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Hate Dating but Still Want Love? The 4 Mindset Shifts That Make You Want to Try Again

from We Need To Talk with Dr. Darcy Sterling

70m 50s

Hate Dating but Still Want Love? The 4 Mindset Shifts That Make You Want to Try Again

Dating today is increasingly shaped by exhaustion, fear, and a shift from possibility to protection. People now approach first dates with a checklist of red flags, quickly ruling out potential partners as a form of self-defense, rather than openness and curiosity. This behavior is rooted in past disappointments and the emotional toll of repeated bad experiences, which has transformed dating into a chore rather than a hopeful journey. The overemphasis on detecting flaws or making quick judgments reflects a deeper issue: a lack of self-awareness. Many people who speak in generalizations about groups (e.g., "all men suck") haven’t reflected on their own patterns or taken responsibility for past relationship failures. True standards should focus on values and behaviors, not superficial traits like job titles or appearance. A first date should not be about deciding if someone is "the one"—its goal is to have fun and decide whether to see them again. The pressure to make a judgment too soon is unrealistic, akin to hiring a job candidate after just one interview. When people stop expecting a perfect match and instead focus on presence, vulnerability, and mutual enjoyment, their experience improves. Many find that taking a break from dating helps them reset emotionally and regain self-trust. This pause allows them to rediscover joy and curiosity, often leading to a quiet but sustainable return to dating with more confidence and authenticity. Ultimately, the key to healthier dating lies not in avoiding risk, but in embracing the uncertainty and vulnerability that real connection requires.

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I'm interviewing this person for the role of spouse while simultaneously hunting for red flags. I also hear you saying that they're coming into these first dates really not wanting a second. If they can, if they can possibly rule someone out in the first date, that's their preference. Behaviors that they're honing in on start to feel like they're adhering to their bottom lines or to their standards or deal breakers. But they're actually functioning as there was a time back in the beginning before the apps felt like so much work. Before you had rules about how quickly to respond, how much to share, how many dates to give someone before deciding whether they were worth your time. There was a time when meeting someone new in and of itself felt exciting. You would wonder who they were. You could imagine possibility without immediately calculating risk. And then, somewhere along the way, dating stopped feeling like possibility, and it started feeling like something you had to get good at surviving. This is we need to talk, Dr. Darcy Sterling. It stopped feeling hopeful and started feeling like a chore. You got tired of getting your hopes up, tired of putting in effort and getting so little back. Tired of wondering whether the person you just started liking was about to disappear. And after enough of that, something inside you starts to change. You stop walking into dating thinking, maybe this could be fun and you start walking in thinking, how do I make sure I don't get hurt again. And once your goal shifts from connection to protection, your behavior starts changing with it. You become quick to rule people out, more alert to what might be wrong, less willing to give something enough time to become clear. From the inside, that can feel like growth, like standards, like discernment. Sometimes it is, and sometimes it's exhaustion making decisions for you. A lot of done is the host of seeing other people, a podcast about modern dating and what people are actually experiencing when they try to find connection. She spent years talking to people about dating in real time, which makes her exactly who I want to ask about what dating itself might be doing to us. A lot of done so good to see you again. So great to see you. It's been too long, even though it hasn't been that long, but you just make my day better. So hi. Thank you for joining me on We Need to Talk. You have spent years hearing about dating in real time, unless interested in whether dating apps are good or bad, then in what the experience is actually doing to people. So when you hear from your audience, what are people becoming exhausted by? Oh, so many things. And I actually, I want to start by saying I agree with not talking about whether dating apps are good or bad because they're not inherently one or the other. Or what you make of them, they're a tool, but you need to use them properly. And I think one of the biggest issues in dating right now is everyone is so burnt out from swiping and they're burnt out from going on date after date after date and not finding what they're looking for, but seeing everyone around them somehow end up in relationship. And then they start to question, well, what's wrong with me? And once you get into this window of dating sucks and everything is awful and it's never going to happen for me, you're not actually giving yourself the opportunities that you otherwise would have to meet people because you're really closed off. And if your ultimate goal is to find love, you've also stopped believing that the process is going to get you there. So I want to hear like the very detailed specifics of what that looks like when people become exhausted, what are they actually start doing differently in how they date? You know, I think it's not just that they're exhausted from going on bad dates, they're exhausted from swiping, they're exhausted from matching with people and not having conversations start, they're exhausted from conversations starting and then dying out and people disappearing and having the same conversation over and over getting excited and being disappointed or wondering, you know, okay, well, this date was actually good, but you know, is it going to go somewhere or not? Or this person isn't responding to me and it's a Friday night, are they going on dates with other people? So by the time you actually get to a date with a person, you're already feeling so depleted. And I think what I often see is that, you know, sometimes we say that people aren't necessarily giving their dates enough of a chance. But I also understand why because it's hard to show up being genuinely curious every time when you feel like you've had the same first date, 45 times. But don't you think that that's diagnostic and like part of the problem? Like why are you showing up the exact same way around 20 different people? Aren't they bringing out different parts of you? I feel like I'm a different therapist with every client I show up with. I mean, for sure, there's a common denominator. It is me. It's one personality, one human being to be sure. But like I feed off of their chemistry, I feed off of their energy. I'm a different host with you, which is why I was looking forward seeing you again. Then I was last week with my last guest. Then I will be next week with my next guest. I'm not like the exact same. So isn't that part of the problem? Like why are people, are they showing up with a checklist on first dates? Like what's happening? 100%. Everyone has a checklist of what they're looking for. And I think at this point, people have a bigger checklist of what they're not looking for. So people aren't going into a date being like, I'm going to have a great conversation tonight. I'm going to have a lot of fun. They're going into it being like, alright, I'm interviewing this person for the role of spouse while simultaneously hunting for red flags. And the second they find somebody who says something or does something or wears something that gives them the ik or rubs them the wrong way. They're like, okay, bye. This isn't working next. And I think part of it is the fear of like, well, what if I actually give this a shot? Then that's even more energy. And then that's more fear of, well, I could end up hurt. So it's easier to just look for reasons to not continue it. Even though again, the ultimate goal is to find a partner or someone you could build a partnership with. I think you're landing on something important, which I see all the time behaviors that they're honing in on start to feel like they're adhering to their bottom lines or to their standards or deal breakers, like it feels like discernment. Yeah, they're actually functioning as armor and the person, the data or things that they are getting better at dating when actually they're really becoming much less available for the very things that dating requires, like tolerating uncertainty and getting to know someone over time. And truthfully, yeah, I mean, I hear what you're saying, they don't want to invest the energy that would be required to give someone a second and a third date, but like, you've got to allow for more than a one or two hour conversation to determine whether or not someone is right for you. And that is called leaning into vulnerability. Right. And it's scary because we've been hurt before. But no, I mean, I think it's such a good point of like people are unintentionally going into it, thinking, I'm going to find the reason this won't work before I have enough information to actually know. Like that is how they are acting when in reality, like, yeah, you should not pursue things with people who aren't right for you, but you have to approach it in a way of, I know what matters to me. And therefore, I'm not going to force something that isn't right. So I think, you know, people are afraid to either settle or to be too picky or not picky enough, but when it comes down to it, you have to actually know yourself and know what type of values you want in a person and what type of partnership you want. Because it's so easy to like, I hear this all the time of like, yeah, you know, like, they really wanted to share food and I don't like to share food. So that's just it would never have worked. So like, I'm not going on another date. And it's like, does that actually impact the type of partner this person would be for you and the way they would show up in your life. People are confusing commonalities for common values. Yeah. And those are vastly different things. I also hear you saying that they're, they're coming into these first dates, really not wanting a second, if they can, if they, if they can possibly rule someone out in the first date, that's their preference so that they don't have to invest time. There's a thing, like, you think the problem is that you do it. you picked the wrong partner. And I have news for you. It's that you didn't recognize your patterns well enough to trust that you can run interference on them. It would be so much more convenient to pick someone who is never going to rub up against your soft spots or rub up against your issues, but that is so unrealistic. Certainly there are people who will do it more or less. But when you've done your own work, and I'm going to sound sanctimonious here, I don't mean it that way. Like, when you have reflected on yourself and not just decided that your past failed relationships are because you picked the wrong partner. I mean, outside of abusive relationships, clearly I'm not talking about that. I'm talking about like, you know, it didn't work out. It was a good run. It just didn't work out. In those scenarios, I can promise you, I can help you hone in on what you didn't recognize in yourself that allowed you to keep dating and then eventually being in a relationship with somebody with whom the values and the principles were not well aligned enough. So in other words, it's like you, you've just externalized responsibility for an internal job. If you've done the work, you can trust yourself to go on a few dates, date for a month or two, and extricate yourself, but it's that you don't trust yourself. That's what people are missing. And that's why they're trying to make, they're putting such an emphasis on this first day. It's so intense. Yeah. And one thing that you and I talked about on seeing other people when we've recorded together a few weeks ago was how, listen, there are certain people who have done the work. And then there are certain people who, and I think there's more people who haven't actually done the work, but they've consumed a lot of therapy talk from social media. And therefore, they think, they've done the work. They think they're healed. They think they're evolved to the point where, well, they can't possibly be the problem. So everyone else is the problem. And then we get into the culture, which I hate of like, well, I hate men, all men suck. Because all men are going to go out on a bunch of dates with you and then ghost you, where all men are not going to be faithful, like just because two people have hurt them in the past. And that can exist while also being someone who has done the work and is healed and is genuinely looking for and ready for a real partnership. What you just said is literally one of the greatest red flags that a client can report to me. If a client goes out with someone and I hear that the person that they went out with was speaking in generalizations like this, all men suck, all lesbians suck, all New Yorkers suck, all people from big cities suck, you know, tech bros suck, these people suck. Whenever I hear people speaking in generalizations like that, here's how a therapist processes that. Immediately, I hear you have not done the work on yourself to recognize that the takeaway can't be a group of people. Just, I mean, guys, let's just, let's just, let me give you an easy analogy. Imagine you did that with race or religion. You, we all know that that would not be cool. It's not any more cool to do that with any, any subject. Yeah. Because it's not all. It's, you had a bad experience. And your takeaway was not that you missed something or that you did something wrong. It was that this whole group of people, they suck. And they're out to get you. And they're exactly. And somehow everyone else in the world winds up partnered. But you, there's a curse on you. And look, I don't mean to sound unfair, but I can sound unfair because if everything in your life is because of other people, you're fucked. You have no agency. You have no power in the world. So if you're going to go out and speak in generalizations like that, you absolutely cannot claim to have done any sort of work. What they're doing is they're consuming psychoeducation. And they have no idea if they're consuming it accurately or if they're just ingesting sound bites because they haven't actually sat with a therapist. Right. I think back to when I was single and I was stuck in this pattern for years of going on a few dates with a guy starting to really develop feelings. Like I definitely like caught feelings very quickly and started to like future trip and all that great stuff. But I kept running into the situation where, you know, we'd get to like maybe five, six, seven dates where I'm thinking like, okay, this is definitely starting to go somewhere. I wonder where. And then they would hit me with the, I really like you and I love hanging out with you. But I'm not looking for anything serious right now. But I'm still down to keep hanging out if you're okay with that. And to me, every single time, time after time without fail, I was like, okay, you know what? They don't know me well enough yet to know that they want a relationship with me. But what I'm hearing is they like me and they really like spending time with me and they want to keep spending time with me. So even though I want a relationship and they're saying they don't, I'm hearing that they don't yet. And so every time I stuck around and every time, you know, a few months later, once I'm meeting their friends hanging out with them four or five times a week, sometimes even meeting their families, I'm starting to think like, okay, we're real, it's like this conversation's going to come up again. Like they're treating me like a girlfriend. Like I think I almost have a boyfriend. And then the conversation would come up and they'd be like, no, I told you I don't want a relationship right now. And I thought you were okay with that because you heard me say that and you stuck around. And at the time, I thought this was something that kept happening to me and that, you know, everyone was doing to me and it was just like this is always going to happen to me. And it wasn't until I got so tired of it happening and realizing that like, in a way, I was breaking my own heart that I finally, I had another guy say this to me and I was like, you know what? I've been down this road and I know how this ends and I also really like you and I really like hanging out with you and yes, it could be really fun for us to hang out for a few more months before you move to another state. But I need to choose myself and say no. And a few months later was when I met Jay, who I have been with for five and a half years and married to and like had I not started to choose myself and realize my agency in the situations that I was in, I never would have gotten there. And in defense of you, I'm just going to run interference here and be a little protective and a little big sister-ish. You are an optimist, right? You were hearing and you were tracking accurate like data points like people bringing you around their friends and family. Here comes the public service announcement. If you want something casual and you don't want to be a douchebag or labeled that way, you don't get to bring her around your friends and family. You just took up with her privately and quietly and you don't introduce her to your tribe because she is tracking that as being integrated into your world. And yes, that is so misleading even if you once told her, I don't want anything serious. So that's maybe in protective of you. Thank you. And also, I think it is fair that so the other thing that you were doing is you were like, he likes me and he doesn't want a relationship yet. So you were tracking potential and we can't, we can't date potential. We have to look at the person and not see who we imagine they're going to be in a year, in a week, in a month, in a decade. Who is Ilana today? Who are you today? That is the person somebody has to be prepared to sign up for. Not the person that they think you can become. The minute we start doing that, we start filtering out the language that the person is giving us for the vision that we would like. And those two things aren't always the same. Yeah. I do love that you found your agency in that. And I want to concretize that for one second. You use some vague terms that I want people to, I want to make this very black and white for people. What you decided to do was hear the words out of their mouth and believe them. It wasn't, I chose myself. Yes, that may have been part of your internal dialogue. But that's so vague. It's really hard for people to work. off of and identify the takeaway. What you did was you decided I'm not going to put my heart out on the line for someone who is telling who is not immediately telling me this is what they want. And yes, so that is choosing yourself. But in a black and white way what you were doing was hearing the words and believing them. Even if their actions spoke to something potentially different. And I feel like something that has helped me over the years and that I've tried to encourage other people to do is to stay really grounded in the facts. We love to assume, we love to try and make sense of things. And so let's say you get back from a date. You'll tell you go on a great date. You had a great time and you left and you both were talking at the end about doing something next week. And there was nothing to be concerned about. You had no anxiety, no stressors at towards the end of the day of like, am I going to see this person again? And then this is what would happen to me all the time is I would get home from the date and immediately spiral of like, oh my god, wait, we said we were going to do something. What if I don't hear from them ever again? Like what if like now now I need the text now I need the reassurance. And what I started doing was actually writing down in my notes app on my phone like, okay, here are the facts after the date. Here's exactly how I feel right now before the spiral starts of like, we talked about these things. We had these things in common. There were these things I'm not 100% sure of yet because we just met and I don't know them well enough to be like, this is the one. So I'm going to like also take note of that to control myself a little bit. But as I left the date I had no doubts that the connection was mutual and that they also wanted to see me again. And so two days later or the next morning if I hadn't heard from them or two days later if we had texted a bit and made a plan but then they weren't being that communicative I could actually open that note and look back and be like, okay, everything is good. I'm creating drama in my head for the sake of creating drama and I don't need to be doing that. Let's put the phone down and walk away. And also nobody wants drama. You didn't want drama. Your nervous system started getting jacked up because there was uncertainty because the flip side to excitement which is the early part of the relationship or the dating experience which is so much fun can be such a great time when it's short-lived and you haven't been an aronsum repeat cycle for years and years is that there is uncertainty about what to expect. And so your nervous system would get jacked up about that. And what you did was you created like a grounding technique for yourself. You'd finish the date, you'd write down the facts, you'd write down your feelings and then you had a source of truth to go back to. It was really smart. And it helped. It really did help because I knew that I was going to spiral at some point because I usually did. And I think one of the reasons I started doing this was after there was a time where I had been on maybe six or seven dates with this guy and everything was going really well and you know I hadn't heard from him for like a day. And I panicked and called my best friend and was like Sarah I haven't heard from. Let's call him John. I haven't heard from John and like I just don't know what's going on. Like I feel like this hasn't happened before with him and she was like on a every single week since you met him. At some point you have panic to me saying I haven't heard from John. And guess what every single time you have heard from John and everything has been completely okay. And I was like oh. And she was like literally scroll up in her text and I'm like oh my god she's so right. Every time I did hear from John but it was because I was so used to not hearing from people or getting excited and then being let down that it makes sense that I had my guard up and I'm not going to fault myself for that. It's a very normal part of the experience but going back to you know what we were originally talking about. This is why dating is exhausting and this is why everyone is frustrated because oh my god what is happening in our brains as we're trying to just find someone that makes us happy. The uncertainty is what's happening in people's brains. The flip side to excitement is uncertainty which can feel like stress and it can feel like anxiety and it is hard to manage that especially when you can go six, seven, eight dates in and still potentially like not have a mutual discussion about this is incompatible or this isn't working for both of us and one of you gets veto rights over it. That's a good amount of time to have invested for it not to work out. Give me 10 seconds of your time and please follow the show right on the app where you're listening. Thank you. What do you see people doing different that they think is helping them date smarter but is actually making it harder for someone to get close to them? Oh that is a great question. What are people doing that they think is helping them date smarter? I think people are actually trying to have a much stronger filter for who they are willing to go on and date with because they don't want to keep going out on dates that are duds. So they're trying to have longer deeper conversations beforehand on the apps. They're trying to you know assess before like am I actually going to have a good time with this person but that's really really hard to assess before you're actually in person or at least on the phone with them. And so they're putting all this extra energy and effort into getting on to the date with a person but then by the time they get there again they're already like well let's go red flag hunting instead of actually giving the person like a real clear shot. I think one thing that people have not been doing enough of that is a tried and true as old as time method of dating is actually just like going out and meeting people. I was talking to a friend today like oh like in the wild like like go to a bar yeah like not not have a predetermined date not have it in the bank that there's I I want to hear what you have to say about this and then I have so many thoughts about this go like whatever happened like going to a bar and talking to someone that you think is attractive and then hearing their voice and being like oh okay we kind of hit it off I want to know more about them like people literally don't do that they will go to every type of singles event and be miserable at it they will be on six different apps they will try working with matchmakers they will do everything to avoid just going out. Go out think about the vulnerability involved in that and the uncertainty with that and your whole generation you know in defense of the whole generation has grown up accustomed to having the date predetermined they know who they're looking for when they walk into the bar of the restaurant or the coffee shop and as opposed to I mean have you gone out lately because I can tell you when I go out I can't believe how people aren't mingling I can't believe how people are just with their groups and nobody is looking up like young people are not looking up they're not looking around people are not walking around the bar they go to the bathroom they come back like it is so drastically different from when I was in college and a young adult and in a way I kind of think that there's some freedom in that because when you go out with your friends you're so with your friends it's not a duplication of goals there you're literally there to hang out with your friends you're not on the prowl but the amount of soft skills that are like eroding so when you say why don't you try going out there's a lot of vulnerability involved in walking up to a strange or or like I caught like signaling with your eyes that like you locked in on someone and you would be open to a conversation and then because they don't necessarily have those skills well developed they may not even be tracking that a woman has just made eye contact and would be open to a conversation it's such a fucked up situation right now I mean but tell me are you seeing that as well or am I just seeing that I definitely am seeing it and I've also been places where I do see people talking to each other and I do see people like showing up by themselves and just like sitting at the bar having a drink with you know twiddling their thumbs looking at their phone with a book and yes again like is that approachable not necessarily but at least they're there they chose to go and give themselves the opportunity to be surrounded by other people so I'm not saying it's easy it's not like snap your fingers go out but if if you are only relying on the dating apps to meet somebody I think you're doing yourself a disservice I agree and there's something that is lost in that organic meeting of a stranger in a place because you don't get to experience when you have a predetermined date you walk into a place yes you have excitement and butterflies that are in a different category, then you have just approached a stranger or a stranger has just approached you and you have no idea where this conversation is going to take you and it could be a connection that it's such a different experience than going into a place and being fairly certain, you know, hopefully that the person's going to show up there for you to meet you. Right. And though I talked to someone this morning who was like, yeah, I went on a date last night and it sucked. I'm like, okay, well, what about it sucked? She's like, honestly, I just didn't like his voice and so from the second we got there, I was like ready to go. And those are the dates we don't need to be going on. Like those are the dates that are making dating so exhausting. But I mean, you know what? You hated the person's voice. Do you know the amount of choice that has to be available that that becomes a deal breaker? That is, and I'm not doubt. Listen, I think dating apps are amazing. I think they've opened up everybody's world. They're part of the reason why we live in such a progressive world because people are no longer relegated to their geographic location and like the six degrees of separation from the 30 or 40 people that they're likely to meet over their lifetime. Now they're meeting people from all over all over the place that they would normally not have a then diagram and overlap with. But the downside to that is that there are so many options. That people can be like, I didn't like their voice. Right. Or I didn't like the shoes they were wearing or the way they ordered or the way they ate their food. I don't even know what to say. If the episode is about dating fatigue and that fatigues me, I know. When the concept of the Ick went viral, I wanted to like pull all my hair out. I'm like, this is so dumb. Why are we coming up with like a bit about the little things that we're picking apart about somebody that literally don't matter? That is dating app culture. That is a consequence of dating app culture. I want to circle back to standards. We were talking about standards and what people are doing differently now on first dates and you were talking about like people are really honing in on red flags. They're red flag hunting. I want to make sure that we distinguish that from having standards. If someone is inconsistent or disrespectful or clearly unavailable, that matters. But if every imperfect signal gets treated like proof that the person is unsafe or not worth another date, then what you're calling standards is actually perpetuating the very dating culture that people are exhausted by. Your standards aren't, you know, the level of college this person attended and how tall they are and what type of job they have. Those aren't standards. Standards are about how someone lives, how someone treats you, how someone behaves around other people. If they're communicative, they're kind. Those are standards. Their standards should be about their values and what they want in the future. And you should be thinking about do those things align with what you want. Just because somebody has a job that you're unfamiliar with or that your ex also had or went to a college that you've never heard of or grew up in a place that's less desirable, like that again, that doesn't impact the type of partner they would be to you. And so sure, you can have preferences. I'm not saying don't have preferences. You know, if there's a certain type of person you're attracted to, great, I'm not telling you, be attracted to the complete opposite of that. But recognize your standards and what like, I don't want to say the bare minimum because we shouldn't be just going for the bare minimum. But like, recognize what you're willing to accept and like what you actually want. You know, think about the people in your life, the relationships surrounding you that you look up to and admire and that you would want one of your relationships to be like and then separate those things from your preferences, the nice to have. I think that's such sage advice. People don't think enough about relationship role models. Yeah. And I don't know if we have enough of them to be honest. And that's probably why people don't think about them enough because they're like, wait, what's that? What do you mean? I remember being a young adult. There was, I mean, and this is, this is indicative of the problem. My best friends, parents were just so loving. I mean, it's 40 years later and they're still happily married and they're such a great couple. I credit the wife for everything. She just has such a spirit about her. But I remember watching them in my early 20s being like, that is what I want. That is what I want one day. And I was, I remember tracking the characteristics, the character traits that I loved about them. They were just so fucking kind and thoughtful towards each other. And it's not like neither of them saw the others flaws, but you never questioned if they were on the same team. And everyone wanted to be around them. Everyone wanted to be in their company because they just made other people feel good and hopeful about life. And she had a high school education, a high school education. And some of the greatest relationship advice I have ever received in my life. And I've gone to the best of the best of the best of the therapists in the world. Because that's who they tell the therapists to go to when you're getting a PhD. And I got better advice from this woman, to be honest with you because she spoke, she spoke. And she was so smart. I remember like this one thing that she told me, Dorsi, use your good China every day. Don't save it for the guests. Use it every night when you eat dinner because that's the person who deserves the best. I mean, and just you don't have to take it literally. But also she would say, you know, when you come home from work, you know, remember that your partner has also been out in the world all day long. And like you don't necessarily have to throw on the sweats and wipe off the makeup so that they come home and they don't see the greatest version of you. Like you can give them 15 minutes before you do that. And I honestly, I think that those little tidbits that may sound archaic to people. And I don't give a shift. They think it's archaic. We are visually attracted to one another. And if you're not going to put effort in for your spouse or partner, I don't know how you expect it to work long term. I've got news for you. But it was really about the underlying theme. Like this is the person you want the best for. You want to show this person as opposed to what comes naturally to us. I think what I know, which is that like oftentimes our partners get the worst versions of us. Yeah. And I love the examples you gave because it's also like it's not about the big things. It's about a lot of little things and a lot of little habits that build and that like your habits and your patterns become your life. And I think that's one thing, you know, going just back to like early stages of dating. Like, it's the little things. It's the way somebody remembers something that you said or, you know, realizes that you had a hard day and is like, wow, like how can I make it better? Or, you know, surprises you with one little thing that was just unexpected. Like, I feel like that. I actually, we, Jake and I had a little phase of going to magic shows for like a month, maybe two years ago. And the takeaway from those magic shows is like, the best parts of life are the surprises. One hundred percent. The things that you're not expecting. And they don't have to be grand or crazy romantic gestures and magical moments. They're just something that someone put a little thought into and had you in mind. And you weren't expecting it. And those are hard things to look for when you're just going on the same exact date and telling the same first date stories over and over in the exact same way. Because you know, someone's going to laugh at them. Like, yeah, that's going to make dating really fucking boring. Oh, that's what people are doing. They have their bits. They know what lands and they're going to that's soul crushing. That's for a comedian or a performer that is not for first date or even a fifth date. I mean, know the material that lands. I'm not, I love to make people laugh. I'm not saying that you shouldn't know what's going to make people laugh. But like we have to be open to surprise. We have to be open to just go out and have a great time. Like, what if that was your goal on every first date? And I, I hear it. I hear what I sound like. I understand to those people who have been out there and they feel like it's a grind. That's why you have to take a break every now and then. And we're going to get to the why of that. A lot of what What changes about a date when someone walks in expecting to be disappointed? Oh, my God. The second you expect to be disappointed, you're probably going to be right. You're going to look for reasons to be disappointed. What you're not going to be looking for is organic moments to make the date better. You're not going to be putting your best foot forward because in your head, you've already written the person off, you've written the night off, you're like, all right, let's just get through it. It becomes a self-fulfilling prophecy of, yeah, dating sucks, and this date is going to suck. And maybe it'll be good, but then it'll probably suck. And what is the vibe? I mean, if you want to talk about vibe, the vibe that is coming off of someone who comes in to a first date, you can tell it and no one wants to sit across the table from someone who doesn't want to be there, who isn't giving it their all, like, I think we forget that the other person there is also dating and is also trying to meet someone. And we're like, okay, we just have to go put on the show and try and win them over. And like, we're actually forgetting that they're human too. I see this all the time and I have so many conversations with my listeners and dating coaching clients about this. So like, every woman thinks that men have it so much easier in dating. And every man actually thinks that women have it easier and that women have way more options and that it's up to them to choose. It's actually true if people could be a fly on my wall, I was just tracking that, you're absolutely right. Each sex thinks the other has a clear path. Yeah. It's that, like, they're showing up to the day and it's like, they have to win the other person over and they have to impress. And so everyone's just like putting on this mask and like trying to go through the motions as best as they can, but really we're all pretending to be somebody that we're not. And we're all expecting to be disappointed. And I would say, think about the last time you had a really fun time with your friends. I guarantee it was something that was unexpected or you were like, my favorite days with my friends are like, well, we're like, let's just have a day and we have no plan. And we're open to possibility and we're open to like going into the weird store or the restaurant we've never heard of or talking to the random people like those end up being the fun days, the ones with no expectations. I'm not going into the hang with my friends thinking, oh, this is going to be such a drag. And guess what? I used to do that and then I realized, hey, I shouldn't be hanging out with people who I'm going into the hang out being like, this is going to suck. So I stopped hanging out with those people. And the other piece is that if you happen to find yourself across from someone who has done their work and is relatively like none of us are the poster children for mental health, none of us are. I self included a hundred percent myself included. But if you find yourself by chance across from someone who has done the work and is relatively mentally healthy, they're going to see and feel that vibe and you're going to immediately repulse them. I mean, whether they're a friend, a potential partner in business, you can't just show up with rusty bitch face. Yeah. I'm sorry. You can't show up without trying to get it up. You have to try and put energy into the things that you're doing. And the people that you will attract that will stick around are people who also are wounded. And maybe they have done the work, but they're not as far along as the people who would be would be around you and be like, oh, I know that if that's where this is date one. And by the way, date one is about as good as it gets. It's about as good as it gets. That's about as good as the attitude gets. And if the person comes in super armored, do you want to be the person with the ice pick chipping away at the iceberg to try and reach them? I mean, because there are people that are day tours, day three years, but like really that's a lot of work to get them to saw. So the people that are going to stick around are the ones that are down for that work. I don't want my clients down for that work. Yeah. Part of the reason I think so many people are disappointed when they go on dates is because they are trying to decide in that first five minutes in that first hour in that one night is this person, my future husband, is this person, my future wife? And that is absolutely not the goal of a first date. The goal of a first date should be two things, one, have a good time. First and foremost, because if you have a good time, what do you think that message is to the other person? Do you think they're credited for it? They think it's because of them. Everybody wants to feel like the person in front of them is having a good time because of them. So you're immediately sending out a signal that is going to make the person themselves feel more satisfied and fulfilled by the date as well. And if you're having fun, that's attractive. People want to be around people who are having a good time and who are smiling and happy. So that's goal number one, to have a good time, whatever that means. Even if it's just trying out a new bar or a restaurant that you've been eyeing and it's been on your list for a while, like, okay, you're still getting something out of the date. So go with the goal of, like, having a good time. And number two, the only thing you should be deciding on a first date is do you want to see this person again? Yes, that's it. That's what it comes down to as opposed to what? Is this person my future spouse could we be together forever? Like could I see myself introducing them to my family at the holidays? Like, that is not productive. And I've been to probably 30 weddings in the last five years. And I think often, I'm so sorry to hear that. That sounds miserable. You have no, it's been, it's been a ride. It's your age. You're in those years where it's like, at the end of it, we have a full 12 months until our next one. So we really deserve a reward there. But all of these weddings, I think about, you know, the stories of how these couples met. And the nine out of 10 of them weren't, we had a first date and we knew nobody said that during their vows. Nobody. It was, that it was easy and comfortable and felt familiar and fun. Like those are the, the feelings that were happening in the beginning, not, oh my God, our first date we met and it was fireworks and sparks were flying and I, I went home and I called my sister and was like, that's my husband. I mean, in a thing, if that happens, bonus, yeah, 100%, and what did I do for five years straight in my 20s? I came home from every date saying to my roommates, I think I'm in love. And guess what? None of those people were my husband. Yeah, that is part of the problem. Part of the problem is that there is too much pressure on the first date, the expectation that you're going to know if this is your person on a first date is so unrealistic. You know, have you tried to get a job lately? Do you know how many interviews people make you go on before they decide to hire you? They won't even hire most people in less than five interviews. Am I right? Yeah. Now they have a whole AI interview first, too, before they even decide to talk to you. Right. The point is, yes, we don't want you to have your chat, but rule out your dating potential matches, but you've got to give it more than one date because the pressure that you put on yourself and the pressure that you put on the poor person sitting across from you, it's too much. And what you said is so important. There are so many other things you can get out of that first date, even if the person isn't right for you. You never know when you're going to be doing business with that person. You're going to need that person as a contact or as a friend, like whatever happened a friendship, whatever happened a friendship. Why can't you be friends with the person you matched with? Or even I actually have this thought this morning, there's this specific bar, like a protein bar that I love. It's like my favorite snack, it's it's called power crunch. You want to know where I first had a power crunch bar, how I first learned about it. From a guy I went on some dates with. And I thought about that this morning, I was like, thank God, I went on those dates even though like it ended with me in tears because here it's like eight years later. And this is still my favorite snack. And I don't know if I would have tried it otherwise by any chance as a gluten free. I don't think so. Probably not because there nothing good in life is gluten free and it's all I can eat. I don't know. It's fine. It's fine. I have my aloha bars. Very happy with them, I'm happy for you. How do you know when someone has gone from tired of dating to genuinely jaded? What do you see in someone? There's just a dark cloud and you're like, I have had it. I'm so sick of this. I dread every day. I come home and I'm like, that was such a waste of time. Dating isn't out. adding a single positive thing to your life. Stop dating. The best thing you can do is take a break. If you are like, I spend so much time on the apps and I can't even get to a date and it's exhausting and it's making me feel terrible about myself, take a break from the apps. Dating, yes, it's really hard. Yes, it can suck and it should be fun. You should look at it as something you get to do because for so much of human history, people didn't even get to date. People didn't get to choose their partner. So it's actually in a way like a privilege and a luxury we have that we get to date so many people and decide who we like and who we want to spend our time with and who we feel comfortable with and safe with and who we want to see again. But if you can't find a single positive in dating, if you can't remember the last time you had a good time on a date, spend some time with yourself, with your friends, get a hobby, do something that makes you feel good and that makes you feel more like you and put dating aside. And listen, that doesn't mean that you're pressing pause on your whole life and your timeline is gonna be all out of whack 'cause guess what, it's not working right now, right? It's not working. All you're doing is amassing more evidence that it sucks and that it's miserable and it's like doing an exercise with poor technique. You do a deadlift again and again and again. You're gonna get hurt. Yes, and it's gonna be so much harder to correct. You better off taking a break. I fully agree with you. And then go on a PT. Yeah, take a break, like prioritize yourself, figure out what makes you feel good and the more you can get yourself feeling good and having good times and smiling, the better you'll feel. And guess what, like, okay, maybe a few weeks, a few months will go by and then you'll see someone on the street and be like, that person was really cute. Oh my god. And then like, oh, I wonder if, you know, maybe I could, maybe if I open an app, maybe I'll find them on it. You might just get an itch, you know, it kind of happens slowly where you're like, you have a little curiosity again. That's your sign of it's time to start dating again. People always ask me like, how long should I take a break for? I'm not gonna say one week, one month, one year. Take a break until you decide you wanna date again. I almost always ask new clients to go on a dating sabbatical because the first thing I want to do, first of all, if somebody who is on the apps is coming to me, they're not having success. Something is wrong and that's why they're coming to me. So the first thing I wanna do is I wanna understand what the problem is and while I'm trying to figure that out, which by the way also doesn't happen in one session, I mean, I may have an inkling, but do you know how often I'm wrong? And I know it because I document it. And I've been doing this for 30 years. So I asked them to go on a sabbatical because I don't want them amassing more evidence. I don't want them engaging in whatever is not working for them. So I asked them to take a break and then based on what it is that I think the problem is, that's how long I will ask them to stay off. Sometimes I ask them to stay off for 90 days. It's three months of your life. Three months of your life. If you were training for a marathon, you would invest at least three months of your life. And that is something that is a beginning of middle and an end and if you wanna life partner, it doesn't. It has a beginning in a middle and no end. So it's a larger, long-term goal. And it's worth taking a break from. What do you think about people who go on first dates or any number of dates and talk shit about their exes? Like, well, like, why are you on a date? Like, what do you think that's going to get you? Like, what are you expecting the outcome of this to be that has never once led to a relationship or something going right? I mean, they have no business being on the date. - What does it communicate to the other person? - That they're not over their ex, that they hold a lot of resentment, that they shouldn't be dating, that the person in front of them isn't important enough 'cause they're thinking about other people. Yeah, all of these not great things. - For me, one of the things it indicates is they have an identified their culpability and why that relationship ended. And they're blaming their ex and if they're doing it to their ex, what do you think they're gonna do to you? - I always would say, if someone's calling their ex crazy, you're the next crazy person on their list. - Absolutely. Yeah, absolutely. When someone starts enjoying dating again, what do you notice they're doing differently? - I think it's less about them specifically doing something differently and more about how they're feeling. Like, are they feeling confident in themselves? Are they feeling like they actually have something to offer and that they're not just trying to convince people to want to be with them? I find that when people start to recognize their own worth, they have a much better experience in dating. They start to realize, oh, I also get to choose how I feel about somebody and I'm not just trying to convince them to want to be with me. And they also are less afraid to speak up or say, hey, actually, I don't like this type of food. Like, can I suggest a different restaurant? And then, therefore, they'll have a better experience. Like, I think when you are able to recognize like, hey, I'm not just trying to convince somebody to pick me, but I'm also getting to pick. And this is also equally my experience. They are so much more themselves and that shows too on a date. You know, that comes across and people can feel when you're being yourself and people like that. They want to actually get to know you, but you have to know that you're enough as you are in order for you to show who you really are. What is an example, maybe a personal example of when you wouldn't show yourself versus when you would? What are the behaviors that you would engage in when you would, that you wouldn't, when you wouldn't? When I wasn't confident and when I thought that everyone else clearly was deserving of love except for me because everyone around me seemed to be able to get into relationships except for me. I tried to play it cool and I tried to be chill and I tried all these different versions of following rules that I saw online. And guess what happened when I would do that? Sometimes it would work for a few dates, but then they would realize that, or they would realize I would realize this isn't me, this doesn't feel good. I'm suffering behind the scenes every second that I am playing it cool and being the chill girl because I am not the chill girl. And once I started being my whole like weird silly self who like wasn't afraid to send a text if I had something to say, things started to feel better and dating got more fun. - I love that. I really, really do. So caught up in that example. I think that's so relatable. - Yeah. We talked about this when I was on your podcast. - Yeah. - That playing the cool girl is such a bad long term strategy and it's all we've been raised on. Everybody was raised on it. That the rules, here's how to get them. You know what you're gonna get when you're playing a cool? You're gonna get somebody who's emotionally unavailable. That is what you're going to get. - And in a way, you're manipulating somebody into buying into the idea of you, but it's not actually the idea of you. It's the idea of a fake you. - Right, and at some point your nervous system is gonna feel safe enough with them to suddenly show who you really are. - And they're gonna be like, "What the fuck are literally going to be like, who the hell is this woman?" I thought you were such low maintenance. And now you have needs. You want me to talk and it's like exactly, exactly. That's why as counterintuitive as it can feel both emotionally and socially, 'cause we are raised to be reserved and to wait until we feel safe to really put forth needs. If you wait too long, you're gonna have caught feelings by the time that happens. And then you have too much skin in the game. It's much harder to extricate yourself at that point. - And people are so afraid to ask for what they need. But you know, what's scarier? Asking for what you need or not asking for what you need and then not knowing if this person can show up for you. Like an example, 'cause this comes up all the time with texting. I've always been a big texture. I'm actually a horrible texture now. But when I was single, I really, I was a big texture. I wanted to be chatted all day long. And I went on I think four dates with this guy. And our dates were so great. And I left them feeling amazing. And we always had that next plan made. And so I wasn't uncertain of like, am I going to see him again, but I wasn't hearing from him that much in between the dates And so it made me anxious of like, well, is he not just a big texture or like does he not really like me because to me That's a sign that someone doesn't like me, but then I see him in person and everything is so great And I have no doubt in the world that he likes me. So I decided you know what I'm just going to I'm going to bring this up Because what's the worst that's going to happen like it seems like he likes me if he doesn't like me I'd like to know that 100% so I just brought up I was like this is going to sound like really weird I don't really know how like properly like say this but I feel like our dates are so amazing And I'm always so excited to see you but when we don't talk that much in between dates I start to get the feeling that like you're not that interested and I get really anxious and I know I'm a really big texture and like maybe you're not But I just wanted to bring it up because like I feel like it's it's giving me mixed signals and I don't know what to think or how to feel And he was like, oh my god, no, like I'm so sorry, like I'm not usually a big texture especially during the week I like I don't mean to be sending mixed signals at all but now that I know that you're feeling that way Like I'll definitely try and text you a bit more and be a little more communicative in between dates And I wouldn't say this is an example of if he wanted to he would because here's the thing He didn't know I wanted him to until I told him and it took me communicating and guess what? He became an amazing texture and we started communicating a lot more in between dates But that never would have happened had I not taken that risk and yes it was a little scary But I'd rather know exactly and I think that you gave him an opportunity to show you what he's capable of He tested his capacity And he was able to show me that he can show up for me Yeah, you know when I think about dating culture I feel like people especially people have been single for a while and have been at it for a while I feel like they're not clear about how or if the activity of dating has changed them over time And how that might be impacting their experience and the experience of the people that they're dating Which then contributes to their takeaway that the date sucked What do you think about that? That's an interesting question You know what I think about that is if the experience of dating and the dates that you've been on have changed you for the worst I would say that you owe it to yourself to go on more different types of dates and have a bigger variety The date doesn't just have to like in our head we think a date is like getting a drink at a bar, a wine bar or cocktail bar, a dive bar, whatever type of bar Like just getting a drink with somebody If those experiences to you have not been positive, have not been enjoyable, have made you feel down about dating Try something else Go do a paint and sip class or go for a walk and get ice cream or go to a park and have a picnic or go to a board game bar Like go do something different and switch up what dating actually looks like It doesn't have to be the exact same thing over and over because that gets really boring and stale for everyone And you owe it to yourself to have a positive experience So I don't even know if this is answering your question or just some weird tangent I decided to go on But I think part of why it starts to feel so dull and repetitive and doomed is because we're doing the exact same thing over and over and having the exact same conversations every single time So I would say switch it up do something different You did answer my question and I love the way you answered it because you landed on the behavioral manifestation of it So I'm going to try and compliment that and give an internal idea of what to do if you're feeling like dating is just resulting in the same miserable outcome over and over and over again I always like people to be able to see how or if they are contributing to this negative experience that they're having So I tell my clients to engage in a dating audit and it's basically four questions You have to ask yourself first, what is the goal? What am I still trying to get from dating? Are you looking for a long-term relationship? Are you looking for hookups? Something casual? Are you looking just for a short-term relationship? Ask yourself what you are specifically looking for The next question is about pain. What part of dating is hurting or exhausting you? Is it that your results suck? Is it that it's not fun to go on these? You have to separate and untangle what the parts are that are Resultaining you being unhappy or distressed. The third question is recent shift. You have to ask yourself what you have started doing differently because of that pain Because so often that pain results in people even uping their standards which are not really standards they're just armor intended to keep them from being hurt again so it's important to ask yourself how has my behavior or my thinking shifted since I've been dating And then ask yourself about the consequence. What is that shift costing me? And here's the brutal part. The thing that that recent shift is costing you is very often the thing that you came to dating to get in the first place Once you can see how either your behavior or your thinking or your approach to dating has changed, things you start to have options because now you know what that protection and armor is costing you And I love this format. I think we all like to solve problems. Maybe we don't like to but life is partially about solving problems. You and I like to solve problems. But if someone was facing a problem at work, what would they do? They would probably try and solve it. They wouldn't just sit there and be like, well, this is just never going to work. And no matter what we try, it's not going to happen and everything sucks and everyone else is able to figure this out, but I can't. So I'm just going to sit here and twiddle my thumbs and be miserable over here. And I'm just going to keep doing the same thing that's going to run into the same issue and then we're never going to get that end result we want. We wouldn't do that. We wouldn't do that in any other part of our life. Right. So why do we do it in dating? And I think when you can take a step back with often the help of a therapist, you can start to actually realize, hey, maybe there are decisions I've been making over and over that aren't actually serving me or maybe I've just been doing this because I thought that that was the way it was just supposed to be. And I never actually considered that there could be a better way or a while there's a pattern that I'm starting to see. Oh my god, I've never zoomed out and looked at all of this. I do think there are so many ways that we can help ourselves if we actually pause and took the time to look at the situation from a different lens. But that feels scary and and we're not the problem everyone else is so we don't do it anyway. You have to pause to do that and pausing is something that is hard for people to do. Most of us would rather do the same thing repeatedly than to pause and sit in the discomfort and the space that arises and contemplate either alone or in the company of a friend. I mean, your friend was like a lot to look at your text to do this every two weeks with me. I mean, everybody needs a friend like that. But, but a friend, not your entire group chat. Oh, right, because that could be so embarrassing, right? Not not even not embarrassing, but you're getting so many mixed opinions and everyone is bringing their own baggage into it. Right, you're not opening this up to five of your girlfriends because you're going to go crazy. Yeah, that's not productive. One trusted friend, not the whole group chat, not the whole sleep way camp bunk, not the whole sorority pledge clad like there. No, one friend. I want to always my final question. What is one idea about relationships that you think people get wrong? I think that people are looking for the perfect person and they forget that first of all, we're not perfect. Like none of us are perfect. We're looking for someone who is imperfect, who is going to grow and change on their own and with us and in ways that we could never expect. But I think so many people are looking for the perfect person to come and sweep them off their feet. And if you're looking for that, you're never going to find it because it doesn't exist. Sage advice again, I try a lot of done. Thank you for this. Where can people find you? Thank you so much for having me. This was such a treat. You can find me at a lot of done on Instagram and TechSack or seeing other people on Instagram or my podcast seeing other people wherever you get your podcasts. And I was on it recently, you can listen to that episode right there. Thank you so much. This was great. If there's someone in your life who needs to hear this conversation, show them some love and share the episode now. And make sure you're following the show wherever you listen so you don't miss the next conversation. I'll be back on Tuesday with more. I'll see you soon.

Podcast Summary

Key Points:

  1. People are increasingly using dating as a tool for self-protection rather than connection, leading to quick rule-outs and a focus on red flags instead of genuine curiosity.
  2. The shift from hopeful, open-ended dating to a survival-based approach stems from repeated disappointment, exhaustion, and the fear of being hurt again.
  3. First dates are now often treated as evaluations for compatibility, with individuals mentally preparing to disqualify others before meaningful connection can form.
  4. Generalizations about groups (e.g., "all men suck") reveal a lack of self-reflection and indicate that people have not done the internal work to understand their own patterns in relationships.
  5. True standards involve values and behaviors, not superficial traits; mistaking preferences for standards leads to premature rejection of potential partners.
  6. The pressure to decide if someone is "the one" on a first date is unrealistic and creates unnecessary anxiety, undermining both the experience and the possibility of connection.
  7. Vulnerability, curiosity, and presence are essential for real connection—yet people are often depleted by overthinking, over-planning, and a lack of trust in the process.
  8. Taking a break from dating when it feels exhausting allows individuals to rebuild self-worth, which ultimately improves their ability to form authentic, lasting relationships.

Summary:

Dating today is increasingly shaped by exhaustion, fear, and a shift from possibility to protection. People now approach first dates with a checklist of red flags, quickly ruling out potential partners as a form of self-defense, rather than openness and curiosity. This behavior is rooted in past disappointments and the emotional toll of repeated bad experiences, which has transformed dating into a chore rather than a hopeful journey.

The overemphasis on detecting flaws or making quick judgments reflects a deeper issue: a lack of self-awareness. , "all men suck") haven’t reflected on their own patterns or taken responsibility for past relationship failures. True standards should focus on values and behaviors, not superficial traits like job titles or appearance.

A first date should not be about deciding if someone is "the one"—its goal is to have fun and decide whether to see them again. The pressure to make a judgment too soon is unrealistic, akin to hiring a job candidate after just one interview. When people stop expecting a perfect match and instead focus on presence, vulnerability, and mutual enjoyment, their experience improves.

Many find that taking a break from dating helps them reset emotionally and regain self-trust. This pause allows them to rediscover joy and curiosity, often leading to a quiet but sustainable return to dating with more confidence and authenticity. Ultimately, the key to healthier dating lies not in avoiding risk, but in embracing the uncertainty and vulnerability that real connection requires.

FAQs

They’re often doing so out of fear of getting hurt, not because they’ve clearly defined standards. This behavior reflects exhaustion from repeated disappointment, not genuine discernment, and can stem from a lack of self-trust or unresolved emotional patterns.

Standards are about values like kindness and communication. Red flag hunting involves dismissing someone based on minor imperfections, which is often unrealistic and leads to missing meaningful connections. True standards don’t rely on surface-level judgments.

People become overly cautious, expect disappointment, and focus on finding flaws rather than building connection. They often go on dates with pre-set expectations and immediately spiral when things don’t go as planned, leading to emotional depletion.

The real issue isn’t the apps themselves, but how they’ve been used—leading to endless swiping, superficial judgments, and a lack of real human connection. The problem is the cycle of disappointment that builds from relying on apps without emotional investment.

It reveals they haven’t done internal work to understand past relationship patterns. This mindset externalizes blame and shows a lack of self-awareness, making it impossible to genuinely form healthy, reciprocal connections.

By taking a break from dating apps, focusing on self-care, and rebuilding confidence. This pause allows space to reflect, heal, and return to dating with a clearer sense of self and healthier expectations.

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