The speaker reflects on her six-year marriage to Matt, acknowledging that her time as a single person was just as transformative and valuable as her current relationship. She emphasizes that being single isn’t less meaningful—it’s a crucial phase for self-discovery, confidence, and emotional growth. She critiques how modern dating apps have turned dating into a mechanical, stressful process, stripping it of fun and spontaneity. To counter this, she advocates for relearning the art of in-person flirting—starting with simple, fearless interactions at bars or social settings—as a joyful, low-pressure way to build confidence and connection. She encourages viewing first dates as romantic experiences, not choreographed tasks, and pushes against rigid rules like fixed locations, drink-only dates, or no kissing. Instead, she promotes spontaneity, fun, and emotional authenticity, reminding listeners that even painful or awkward dates offer valuable lessons. Ultimately, she argues that the chaos and unpredictability of dating—its highs and lows—create the foundation for strong, self-aware relationships. She urges single individuals to break free from social media, take risks, and embrace the adventure of meeting new people, because the experiences of being single and dating are not just valid—they are essential to becoming the person ready to love deeply, wisely, and fully.
Daddy gang, welcome back to another Sunday session.
I am feeling really, really reflective
heading into today's episode because fun fact,
tomorrow is Matt and I's two year wedding anniversary,
which means we will have been together
for a total of six years going on seven.
That is like insane to say out loud.
In some ways, I feel like we've been together
our whole lives, but then another part of me
is like still shocked that I'm married
and I have a husband and I'm a wife.
But as we're entering into this third year of marriage,
I have been thinking a lot about the time
before Matt and I ever met.
Obviously, I feel so grateful and lucky
to be in this phase of my life with him,
but I'm also really grateful for the time
that I gave myself to just be single
and on my own before we ended up together
because even though I'm married,
even though being single can, of course,
be extremely stressful and disappointing at times,
it can also be one of the most transformative
and empowering phases of your life.
And I am so happy now to be building this life with Matt,
but I was really happy when I was single too.
And yes, I know like being singled and being married
are two wildly different experiences,
but what I really wanna emphasize today
is that one, I'm not single.
The other phase is not more meaningful
or important than the other.
When Matt came into my life, I was really enjoying dating.
I was meeting new people.
I was figuring out what I liked,
getting to know myself better, was building my career.
And because of that, I think Matt and I were able
to take our time and not rush into anything.
And I think now looking back,
that was such a huge part of why our relationship
worked so well.
I didn't need Matt.
Matt didn't need me.
We were both so centered and working on ourselves
that it kind of was like, if this works out, great,
but like, don't really need ya.
And like, I'm a very independent person.
And if our lives naturally come together, great,
but like kind of doesn't matter if it doesn't work out
because I'm good on my own.
And I think that was such a beautiful place
to be in when I met Matt.
And because of that, I do think that those early dating stages
between us, they got to just be really fun.
Like they were low stakes and we just both got
to kind of be along for the ride and just enjoy ourselves.
Why I'm bringing this up is because lately
when I talk to my single friends or when I'm reading DMs
that you guys are sending me for questions of the week,
I feel like the experience that I got to have
when I was single is very different
from the experience of dating
and trying to find your person in 2026.
And weirdly, like I know it wasn't that long ago
that I was single, like seven-ish years ago,
but a lot continued.
It continues to change with social media.
And listen, I know it's like not exactly a hot take
to say that dating apps have completely changed
the way that we meet people,
but for better or worse,
they have taken a lot of the curiosity
and the spontaneity out of the process
of meeting someone new.
There's obviously so many positives of dating apps,
but that is one of the cons, right?
And I can totally see how people might feel like
the only option in today's dating culture
is to meet your person on,
on an app.
But I also know that when you're single
and your mentality is in that headspace
where you're like,
oh, I don't really want to be single anymore.
Like I just want to find a partner.
Like I don't want to be going out to clubs
and drinking and going to the bars and all of that.
Like it's almost like you go on that drinks
and you're like really hoping it's going to be amazing.
And then it's like, eh.
And then like you go on the second date
because you're like, come on,
like maybe there's like something I missed.
Like maybe he is better.
On the second date than the first.
Then you're like, oh my God,
this is worse than the first date.
And then you end up ghosting each other.
And like, then the worst part,
you're like, I have to start all over again
because I just spent so much time in the apps.
And then I got out of the apps and we started texting
and then I met him on the date and it was horrible.
And now I'm back to the apps.
Like that whole process I do want to acknowledge
can make you feel a little numb.
It's just the truth.
You start to become numb to dating.
And if you're anything like a lot of my single friends,
then you're probably also at a place where like,
you know exactly what you're looking for.
Your standards are probably really high.
You've done a lot of work on yourself,
but every date you go on just feels like
another disappointing job interview,
another waste of time.
And I think when dates start to feel like this chore
that you have to check off your list,
I think that we really then start to strip ourselves
from the potential to actually have a lot of fun
in the process of getting to know someone
and being single and dating.
And so I am here today, Daddy Gang,
to try to bring a little fun back for you, okay?
We're going to try to make dating feel fun again.
And that is my mission for today's episode.
If you have been feeling hopeless or overwhelmed
with your dating life, then this episode is for you.
I have not forgotten my single girls.
Let's get into it.
The whole point of any romantic experience,
whether it's a first date or a 50-year marriage,
is that it's supposed to make us feel good, right?
Like, why do any of us want to partner up?
Why do we want to partner up at all?
Why do we deal with the ups and the downs of relationships?
It's because at their core,
they're supposed to make our lives more enjoyable
than they would be just being on our own, right?
And if you're single today,
that means that all of the best relationship milestones
are still ahead of you.
The first sleepover, the big first I love yous,
the first trips together, like all of it,
meeting the parents, meeting the friends.
Like there are so many firsts ahead of you
that I promise you, I promise you,
your friends and long-term relationships
are probably jealous that you still get to look forward to.
Like if I could rewind and relive some of the early dates
that Matt and I went on and some of those early moments,
like I would because you can't recreate that feeling, right?
The early dating stages can be truly the best time of your life
if you do them right.
And yes, I obviously know that dating intentionally means
you probably feel the pressure and the timelines
and expectations that I am not.
I'm not ignorant to,
but I also know that like anything in life,
when you get so fixated on the outcome,
it can completely negate the enjoyment
that we get to feel along the way.
We're putting too much pressure on ourselves.
And so I think it's time to lean back into those,
you know, the warm, easy, middle school feelings
when all it took to make your entire day
was just like your crush,
complimenting your ugly gauchos
and being like, damn, Becca, you looking good in those.
And you're like rolling your windows down,
blasting, what is the song?
Like suddenly I see.
And you're like, hey, oh, things are turning around.
Like you're so happy.
I think that's the energy we need to start to channel.
Being in this year, if you are single,
we are going to, that is what we're going to do.
So I want to start at the very beginning.
You're like, what do you mean we're starting?
At the beginning, I'm not abandoning you guys.
Like we're getting into the weeds here today.
Okay.
So we are going to start with flirting.
I'm not going to teach you how to fucking flirt today.
You all know how to flirt.
But I think in my opinion, as a society,
we are losing the art of flirting.
And I refuse to let that happen.
Okay.
Flirting has turned into story likes, fire emojis,
swiping, right?
Maybe a DM if we're getting a little crazy.
No.
Okay.
In person, somehow flirting has become a rare art form.
I literally was reading, please guys, let me read this to you.
A recent study at date psychology found that 45% of men ages 18 to 25
have never approached a woman in person for a date.
I just like, I don't understand.
I don't get it.
Oh, you're so fucking done.
You're so fucking done.
I think this is what we're going to have to do.
Listen, we could do a whole episode on how depressing it is and how men have just like
shriveled up to like almost nothingness, right?
That can be another episode, but that's not for today.
We're trying to stay fucking positive here.
So if the men are going to be annoying losers, we need to take matters into our own hands.
Okay.
I remember back when I was single, I used to go up to seriously, like any guy that my friends or I
thought was hot at the bar and I would just start flirting with him and listen.
Yes.
Sometimes it didn't go exactly as I planned, but like there were.
so many instances where I immediately walked right back to my friend group and I was like okay that
that he's not the vibe he looked hot but he's actually a fucking loser on to the next but like
who cares if you go up and you get rejected who cares like I let me just tell you this story okay
take me back to Brahman oh my god I wonder if it's still open okay we're in like 2016 the year is
2016 I am in college and I am at a bar in the peak of winter with a bunch of my girlfriends on the
soccer team and we are in tiny little bodycon dresses with thick heels and we have like shawls
on like we don't even have fucking coats because we're like I can't afford to lose my fucking coat
because like I can't pay for another coat so you just freeze your ass off in line okay we get inside
of Brahman and it is just heaven there's men everywhere
and all of us are like giddy we're like who should we go up to like who should we like try to like
make friends with and make out with and get guys to buy us drinks and all of a sudden this is like
kind of never happened to me in my life but all of my friends and I see this man across the bar
and it literally felt like there was like a shimmering light above his head it was like a
movie moment we were all like genuinely that is one of the hottest men I've ever seen he had like
kind of longish hair with like a beard and he had like big muscles
but he was like wearing like a beanie and like he had a suit on and I was like he's either like
a surgeon or an athlete like I can't tell which one like he either just like finished a game or
like finished open heart surgery either one let's bang and so all my friends are like that's literally
the hottest guy and everyone's like who's gonna go up to him who's gonna go up to him like someone
has to go up to him like what if he has friends what if it's a connection and we're all sitting
there and all of my friends are like no like we're too young like we're just like fucking losers in
college like don't eat I'm not even worried and I just
leave my friends because we don't have time to worry what people are gonna think about us
I go up to the bartender I say do you have a pen she's like bitch do you want a tequila shot I'm
like a pen honey I get a pen I take this napkin I write my number and my a fake name because at
the time I was thinking that every single person was an underage cop that was like a little trigger
of mine because I was obviously underage I was like oh like don't want to like fully give my
name because if they asked for my ID my name was Catherine I had my sister's ID
it's a whole thing whatever so my name was Catherine I'm at the bar do I write Catherine
I write my number I go up to this man I just beeline it he's under his glimmering light
looking sexy oh so gorgeous let's fuck and I say to him hi and he looks at me like who is this girl
and I go I just want to let you know and I just like would kick myself if I didn't say this I just
saw you from across the bar and you're so fucking hot and I need to introduce myself no pressure
here you go call me I start walking away he's like oh my god I just saw you from across the bar
he grabs my arm oh yeah if you haven't had a hookup just close your eyes sit back relax and
just let this one pretend it's you okay he grabs my arm I turn around this man is looking at me
goes what are you doing you can't open with that and then just walk away from me I'm like oh oh my
god like oh so excited it's working he's like what's your name I'm like Catherine I'm like
I'm gonna have to fix that later if this happens I'm like oh my god I'm like oh my god I'm like oh
going anywhere we start flirting oh my god are you here with friends yeah oh my five girls over
there in the corner we turned they're all like pretending to not be staring at us slurping their
drinks I'm like you here with any friends he's like yeah my two boys I'm like oh what do you do
he's like we just got back from our game I'm like I was like an athlete hunter back then
it's since obviously passed but back then oh I could get a rush I could get a rush it didn't
matter I was like I'm gonna have to fix that later I'm like oh my god I'm like oh my god I'm like
really what you did if you threw the ball if you caught the ball if you hit the ball anything with
the ball I was in and this happened to be a puck okay oh you guys know what I felt for hockey
players back in the day those butts and so I then I'm like oh my god do you want to come meet my
friends great boom done his professional hockey player friends come over by all of my friends
drinks at Brahman we hang out I get his number he gets my number we exchange we text we're good to
and then I have a date with him then I obviously can spare you the details of then when I showed up
and he was like continue to call me Catherine and I awkwardly had to tell him like I'm not 21 years
old he still was interested in me is that weird maybe but we'll get into that later anyways the
point is okay shots drinks athletes fun men dicks vaginas everyone was happy that night because I
was like if this man rejects me who cares who fucking cares if this man rejects me because I
went up to a couple other guys at the bar realized they were freaks and kept it fucking moving but
this man ended up giving my friends and I plans and although it didn't work out with him we only
had a couple dates still was so fun still made me feel alive still got me a little oof down there
so I think the moral of the story is I could have given a napkin to 15 guys that night and been
rejected by 14 guys and I was like I'm not gonna do that I'm not gonna do that I'm not gonna do that
but that is okay it just takes one oh my god what is that fucking quote from Cinderella story like
something of like don't let the shot keep you from playing the game or so I don't that's not
the quote but you guys know what I'm talking about don't stop yourselves from believing in
yourselves that who cares if you embarrass yourself it's embarrassing for them to be so
socially awkward that they can't like engage in a conversation with you and not be a fucking dick
right you know what I mean I know you're all looking good you're feeling good go for it daddy
and when it does click with someone and you go up and you flirt with a guy let me just tell you and
he flirts back and you just like allow like that chemistry to flow and the banter is bantering
you're touching his arm he's touching your arm buying you drinks you're getting his number it
is so much fucking fun like that thrill in your body you're like I am on fire I'm on fire like
even if nothing comes after that night it's also just so much for you right like that energy of
like giving yourself confidence and like giving yourself confidence and like giving yourself
confidence of like oh my god I can totally do this and the only thing between you and having
that moment with a hot guy at the bar is just one getting over the fear of rejection two getting the
fuck out of your house and three getting off your phone and actually being down to like go up to
someone and be like if they reject me it's fine but I'm gonna just go for it okay okay are you
with me are you gonna think about me and brahman with the man under the sun okay guys I also know
it's like a lot easier said than done and also like weirdly why did I have so much confidence
but like I get it like now when you're out of college it's like you overthink things I get it
um but I do think we need to start just like if you have wherever you were your highest peak in
confidence get back to that stage I found an article okay guys we are we're not only talking
about dicks over here we are educating the masses here on call her daddy and don't you ever fucking
forget it I found an article on NPR called the key of flirting it's called the key of flirting it's
not about you by Andrew Andrew limb bong and Andy taggle I want to share their advice okay let's
read this one way to ease the fear of rejection is to view flirting as being more about the other
person than about you we get a much better result if instead of trying to get others to make us feel
good we actually concentrate on making them feel good this takes care of lingering self-doubt that
actually presents itself as questions such as what if they don't like me a lot of flirting is driven
by a focus on the end game maybe trying to get someone's number or buying someone a drink this
goal-oriented way of viewing flirting isn't that helpful but we're so used to flirting as a means
to an end to the relationship escalator which is the idea that you date someone enter into a
relationship get married have kids live happily ever after Etc but if you remove that goal you'll
hopefully instead just be looking to create a mutually
pleasant experience instead of any preconceived goals aim for a few minutes of pleasant conversation
that's much more manageable and can help ease the pressure of any possible rejection if all you're
hoping to do is make someone else feel special for a bit you really realize you actually can't
lose open with a question then test and assess how they're reacting to you remember that flirting
isn't about hitting any preconceived Target other than helping someone else have a good time okay
I agree and disagree with this article like I don't want you guys going in there being like
Todd tell me everything oh my God Todd that's amazing okay wait Todd tell me more like and
you're like okay I literally just had the worst date of my life but I I agree in the sense
of like stop getting in your own head like just try to connect with the person and what I love
about that advice is that it completely takes the pressure off of this big moment with someone like
maybe they flirt with you or maybe
they don't but it doesn't actually matter if you reframe the interaction as just being about having
a nice conversation like shift the flirting mentality from worrying like do they like me
do they think I'm hot are they having a good time like that is going to be such a game changer for
your headspace when you are approaching someone rejection is going to happen it is inevitable it
comes with the territory but like everything in dating that's just a numbers game okay you also
never know what's going on in a person's head and rejection usually isn't even about you like you
have to keep in mind maybe this guy is out drinking because his dog just died and he's
sad. So you hitting on him being like, come here often. He's going to be like, no, but my fucking
dog said in his head, but he's not going to say that. And then he's just going to be a dick to
you. Okay. That's the reason he was dick, but you would never know that. Like if the person you go
talk to isn't into it, then just move along to the next. Like all you're looking for here is just
like a fun chat. And if someone can't provide that, then goodbye to them. We're moving on to
the next. Okay. Let's just have fun. No stakes, no nothing. Like enjoy yourself. What a concept.
Let's start there because clearly we are, we are bare fucking minimum right now, guys. These men
are giving us nothing. And if you're like, Alex, no, that is, it's just too scary. Like I just,
you know, I want to sit in the corner and like, wait for a man to come up to me.
Then maybe let's start with a lower stakes situation. Okay. I want you to just start by
engaging.
Engaging with other normal human beings everywhere you go. I understand again,
this is like, what do you fucking mean, Alex? Like, of course I interact with human beings
on a daily basis. Do you though? Like, I'm not saying I want you guys out there flirting with
everyone in the world. I just mean truly practicing being more open in the mundane
daily moments of your life. When's the last time you complimented someone in line at the coffee
shop? When's the last time you striked up a conversation with your coworker?
In the kitchen. Okay. While they're toasting their bagel chat with the person sitting next to you on
the airplane. Okay. I already regret giving that example. Not for too long. Okay. Read the fucking
room to chat to them before takeoff and then shut the fuck up because it's my worst nightmare.
Someone's trying to talk to me while I'm on a plane. I'm like, Oh, you're going to be chatty
today. Headphones on, shut the fuck up. But you know what I mean? Like I'm saying that you need
to build up that social muscle when you're in situations with zero stakes so that when you meet
someone, you're actually in a situation where you're not in a situation where you're not in a
It's not as intimidating to get the ball rolling. And let me be so clear. I know this sounds maybe so
fucking stupid and simple, but I promise you it's not at this point because social skills have
become something that we do need to practice at this day and age. Okay. Social media has completely
taken over all of our brains, all of our world. We literally sit there and scroll and we feel like
we know people and we feel like we understand people and we're like, Oh, I know her. Oh,
I follow her. You don't know any of these people.
Even if it's your friend. No. Did you call her? Have you texted her in a while? If not,
you don't know any of these people and you're just like playing a video game. Okay. I feel
like we used to be able to actually talk to a wall. I guess I am still sitting here alone,
talking to a wall right now, but you guys know what I mean? Like, I feel like I could back in
the day, make small talk with anyone. But even now I realize like I'm out in the world sometimes
and I'm like, Oh my God, am I being awkward? Like I'm having like weird, like is that what that a
weird interaction? Cause I'm on my fucking phone all the time. Like even just with a barista or
something, like I find myself being so in moments awkward and I'm like, Alex, I need to put my phone
away. I need to stop being obsessed with social media and watching everyone's lives. Like touch
grass or I don't know, go talk to someone face to face. Okay. Like close enough that you can see
the pores in their face. I just think technology has changed the way that we interact with the
world around us. And it's, it's not our fault. Cause that's just what's happening.
Around us. But it is then truly on us to retrain our brains of how to engage with someone face to
face, especially when it comes to dating. And I know it sucks. Trust me. Like I'm so jealous of
my parents. I'm like the way that your generation had it, like the romance and the build and the
in-person meetings and the, Oh, Oh, Oh yeah. Take me back to the notebook days. Like their biggest
problem was like, they couldn't get in touch with each other. Oh,
Oh, little mystery, a little, Ooh, like it's not even ghosting. It's just distance. Oh, like,
yeah, yeah. And now it's like, we're on Snapchat talking to each other. We're on Snapchat,
but we'll never meet up. We're just going to Snapchat until this whole thing fucking lingers
and then dies out. No, if you are messaging a man on Snapchat, knock it off. We're done.
We're fucking done. Okay. I think it's just helpful to work on
that social muscle so that you're ready. When there is someone that you're actually interested
in, you're like, Oh my God, here we fucking go. So let's say you do meet someone in person.
Let's, let's start there. Okay. What a concept. We meet someone that we actually like,
and they're not a complete loser and they're not a complete psychopath. Then you're able to strike
up conversation with them. And it feels like things are going well from there, right? Classic
flirting, boom, like we're ready. But remember if someone cannot hold a fun conversation, that is
not a reflection of you.
And when it clicks and the vibes are there, try not to worry so much. If you're being funny enough,
or if you're being cute enough, if you're being hot enough, like the fun of it is just being,
just be present in the moment, be your fucking self. Okay. So now we're leaving our cages.
We're leaving our dungeons. We're seeing the sunlight. We're meeting men. We're out there.
Okay. The next stage that I want us to discuss is the one that is inevitable. It is important
to something that I know a lot of you may absolutely dread, but I promise it has the potential to
be a night you will never forget. Let's get into a first date.
I get why first dates might be so hard to look forward to. It's a whole thing. You're like,
I got to get ready. I have to leave my house again.
To all of us trolls. No, no, no. This is a good thing that we're being forced to leave our house,
but you don't know if you're going to click with this person, right? It could be awkward. Like
you're just like, Oh my God, I'm kind of like meeting a stranger. And like, I don't want this
to be a total waste of time. Great. Okay. But if you're going into a first date with the energy of
a, here we go again, like, I just got to get through this. Then that headspace is going to
completely affect the entire date experience. So fake it. Okay. It's probably going to be a lot
harder to vibe with someone when you're approaching meeting them, where you're
like, this is a task that I have to get through. And I'm already thinking that you're going to be
worse than the last. So let's just get this over with. So I can tell my friends, I went on a
fucking date. No, instead, ladies and gentlemen, I want to reintroduce like romanticizing your
fucking life. Okay. You need to be romanticizing and enjoying every element of a first date
experience starting before you even leave the house. When you are getting ready, let's turn
on one of our favorite songs. Let's catch up on some shows. We haven't watched face
time a friend. Okay. Take that long, everything shower that makes you feel. Oh, so amazing that
you had to do regardless of the date. Okay. Blow out your hair, put in an outfit. You haven't had
a chance to wear yet. Try on your new lip combo. Do everything you need to do to feel your absolute
best. A first date is an important opportunity to like take a boring, normal weeknight,
turn it into something to actually look forward to. Okay. A random Tuesday in your cubicle is a
is going to end with you potentially just looking so well, you're going to look, there's no potential.
You're going to look gorgeous and you're going to potentially meet someone new. Okay. It's good to
have a different experience than you usually would just like sitting at home. We're watching
Hulu or Netflix again. And here we go. Episode 457 of Grey's Anatomy. Trust me, girls. I love
a good Grey's, but we can pause. We can pause for one night of the week. I also know it can
often feel like, okay, fuck, I'm getting ready for nothing. Okay. I don't want to sit down and
spend. I don't want to put my expensive foundation on this gorgeous skin for a man that isn't shit.
I don't want to waste it. Okay. I don't want to end up crying in the bathroom and crying all my
gorgeous makeup off because what the fuck? I don't want to waste a night. Is it worth it? Because Nicholas last week talked to me about his obsession with toenails.
And I was like, I'm never going another date again. And then the guy before Frank quad,
he literally was talking about, he like likes like mommy, daughter,
porn. Like I'm not, I'm not feeling it. And I so get that Nicholas and for quad, like
far quad, fro quad, whatever. Frogger and Nicholas, they don't exist. They were losers,
but there could be a good one tonight. And so you have to just go with that mentality. Even if
you're lying, lie to yourself, you can lie to yourself and just get yourself through it. Because
here's what I will say. When you put makeup on and you put your outfit on, you feel good. You're
not going to sit on a date. Okay. Because we're going to, we're going to build a shield around
that. When I used to go on first dates, I'd be like, I've never been more gorgeous. Okay. This
outfit slay. I am worthy of someone noticing me tonight, even if it's not the fucking date I'm
going with. And so what I would do is I would always plan a drinks before my drinks with the
person I was going to meet up with. I would go meet a friend. So I'm like, even if I just went
out with a girlfriend and then have a shit date later, it doesn't matter. I got to see my friend.
So plan something.
Or if like, you know, your friends are going out later, you're not wasting your outfit. Try to
have things around. Also get a fucking selfie. Okay. Do a little pregame. Okay. Get a ketchup
drink with a friend over your FaceTime. Like, I don't care. Don't just be like, I'm just going
on a date. And if it doesn't work out, I'm going to rip my extensions out in the fucking cab on my
way home. I'm going to cry. I'm going to rip my eyelashes off. I'm going to put them on the cab
door and I'm going to go upstairs and I'm going to watch the notebook and cry my eyes out being
like, why don't I have a Noah? No, we have a full calendar.
When we have nights of a date. Do you understand what I'm saying?
You're setting yourself up for success. So when it comes to a first date,
i've obviously been out of the first date game for a little bit so i when i was preparing for
this episode i did a deep dive on tiktok to see what advice people were sharing for first dates
and you guys i was horrified i was absolutely horrified i was shocked i was disgusted i was
like no wonder people hate fucking dating right now like i came across video after video of rules
of what you should do and you should not be doing on a first date and i fear we have completely
lost the plot on what it actually means to be seeking a connection with someone because look
i know these rules are coming from a good place like people don't want to be wasting their time
and everyone is looking for ways to optimize the experience of meeting someone but in my opinion
the rules are where the fun parts of the first date go to absolutely die we have to find some
nuance and balance here i am going to tell you the top four rules that i kept seeing over and
over and over and then i need to discuss and tell you why i disagree with almost every
single one of them okay number one they said was to go to the same place for every first date so
you can eliminate any external variables okay we'll get to that number two is to never get
any food on a first date only get drinks okay we'll get to that number three is to set a two
hour time limit for a first date and number four is to never kiss them at the end of a first date
okay well um here's here's here's what i have to say to that no wonder dating feels like a
fucking chore we're stripping out all the excitement and the joy when we start over
analyzing and strategizing to that extent let's start with the first rule which is
go to the same place every time you go on a date okay i understand the idea of being like
i know the place and like i know the lighting and i i know where the bathroom is and i know
the parking situation and i know the way to go to the same place and i know the way to go to the
same situation and like i know exactly what to order like you're just trying to be fully
comfortable i get that but doing this i think that completely eliminates the opportunity to
use a first date as one trying something new think about it you have a whole night blocked
off with someone who is potentially willing to do whatever you suggest right or also potentially a
horrible fucking first date so you might as well get something out of it and like at least go try
the new fucking thai place down the street okay you're like this guy is so this oh my god he's so
but like god damn this thai shit is good or like mini golfing and then you can whack him in the
fucking face with the ball like there's options for mobility here if the date is going horribly
at least they're you're trying the cool new bar down the place that you can find scout out for
your next date and then go there one more time but like use the first date as a way to try
something you normally wouldn't do on your own and then how about it oh my god so cool if he
ends up actually being fucking normal and not a miserable fuck that way yeah if you're trying to
the date can go horrible and you never can see that person again but you're like got it i actually
just had a good time in my opinion the unknown elements of a first date are part of the fun
guys like you need to stimulate all of your senses to get that sense of excitement you're seeing new
things you're smelling new foods you're trying new drinks do not go to the same fucking place
every time you're going on a date it is going to feel like you're back in your cubicle and you're
like bring the next one in marty and it's like oh my god oh my god no then you're like not even
anxious for it you're like barb bring me to the back table bring him in it's like what do you mean
what do you mean no you can you can go to the same place twice maybe if you're if you got a roster
like fine go twice but other than that switch it up for your own sanity babe okay also i think that
like new spots can just like help you get out of your head a bit like get get the fuck out like
we're not going to fucking frank's diner every single fucking time like i get it you like to go
to denny's with your fucking family every sunday don't do it every fucking time you're going on a
date number two which is just get drinks never dinner um let me just say something and i have
to reiterate again the whole point is to have fun on a date okay eating is fun don't let the
internet tell you otherwise trying new foods going to new restaurants is fun why are we denying
ourselves one of the best parts of the experience if some of you are going to say because i don't
want to get stuck there like i like i don't want to like you know i don't want to eat in front of
what if i got stuff in my teeth well if he doesn't like you with a little bit of fucking spinach in
your upper right tooth babe he's not gonna fucking like you when he splooges all over your face
ignore me you know what i mean they need to see you in your best and your worst okay so
eat in front of this man if you're fucking hungry now if it just happens to be drinks
it happens to be drinks but don't be like gunning for the drinks he's like do you want
to order some appetizers you're like no tiktok told me that i can only drink on a date like no
no is this man gonna never see you eat in the entire course of your relationship
no why are we not letting ourselves do it when the stakes are the absolute fucking lowest now
i think people could assume like you just want to be trapped on the date you know food makes
like linger a little bit longer then again why are we going on a first date with the mentality
of just getting in and out that's not the mindset of someone looking to having an amazing night
and also i have up and left at appetizers babe okay i have i have up and left if you
are having that calamari and he is saying ruthless shit you get up you slurp your shirley temple down
and you get the fuck out of there you don't need to stay food doesn't mean babe you're locked in
handcuffs on seated three hours full course let's make it to the sunday you don't have to do that
you can leave free will free fucking will um which leads me to number three okay setting a two hour
time limit for the date uh literally why especially if you're having a good time with someone you're
clocked it gotta go he's like wait why i thought we were having fun you're like it hit that two
hour limit got a boogie like no one of my best friends just became official with her boyfriend
and their first date was supposed to be just like grabbing drinks and then it turned into a full
night bar crawl they literally hit a ton of different spots all around the town they were
like boom boom boom now they're dating oh my god guess how long that date was basically fucking
five hours oh my god look it worked out tiktok good things come when you let yourself enjoy them
allow yourself to just be a little bit more open and not be these strict guidelines boom boom boom
i get it if you're like wanting to keep a little bit of like the mystery and you're just sitting
at dinner and you're like all right we need to like wrap this up just because it's like
we shouldn't go on hour four we shouldn't go on hour three like having the two-hour window of
like feeling comfortable to leave after a normal amount of time yes but don't don't be like setting
your alarm and the alarm goes off and you're like that's time jim i'll i'll be in touch like
swear to god i swear to god daddy gang do not set a fucking alarm on your date um this takes me to
rule number four i think it was number four and this makes me the most annoyed the most annoyed
and maybe i was just a little whore you know but i do believe i had it right on this one
when people on tiktok are saying no kissing no kissing on a first date
no i completely disagree with you i completely how about this also no no kissing on a first date well
sometimes i fucked them on the first date how about that one tiktok um how about i let him eat
me out on the first date and i married him no i'm just kidding he didn't eat me out that was like
the second time but okay listen if you are gonna say to yourself in the mirror before you go on
that first date baby you will not accept a kiss you will not even accept a hug what are we doing
what are we doing like you're skipping the most fun and romantic and magical part of having a
great date with someone like like get in there like if a first kiss feels right it feels right
right the first kiss at the end of the date is seriously what they write movies about and songs
and books okay and what i dream about because it's one of the most exciting romantic human
experiences that you can possibly have you do not need to be denying yourself pleasure
to prove some arbitrary point to be like did you kiss him you're like they're like good girl good
girl get your fucking lips in there both if you want let me tell you a story um i've told the
story many times i'll make it quick matt and i i went in there not knowing who this man is i'm
like oh this hollywood man movie producer what's he gonna be about slowly fell in love first night
i was like oh my god i want to fuck this man unfortunately my sister was staying with me in
the same hotel room so like i probably wouldn't let him upstairs into my legs but like i didn't
because my sister was up there but i can't i came across like i wasn't willing to give it up on the
first date whatever the point is is i went to the bathroom we're leaving we're going to the car
after our full long two plus hour date may i add and he texted me to come
to the back of the restaurant to go the back way and i walk down the long alley and i see him under
the little light in the back and he grabs my face and he pushes me up against the wall in the back
of the parking lot and he starts making out with my face and i came in my pants i was like this is
this is what dreams this is what dreams are made of i come to la i meet this man he grabs me by the
back of my neck puts his hands on my hips puts his tongue down my throat puts me in his car and it's
where to next yeah fuck me like that even if i never saw matt again i've had so many dates where
like i had great first date kisses and i was like oh my god i'm never calling you but oh who doesn't
love a makeout like makeouts are so fun okay and so kiss them the first date fucking sleep with
them the first night like i don't care you have to go based on what feels good to your body and
what feels right to you and so if you have some fucking friends that are prudes that are like you
the first date
you're gonna give
them the wrong
impression and
there. You're just going to think you're a whore. Okay. Maybe for you, Cassandra, but I'm about to
let him in my back door on night two. You don't have to do anal on night two, but you could.
Whatever feels right. You have to be at your core centered with what feels right to you and your
body and what you want to do. And if you want to fuck or you want to make out, or how about this?
If you don't want to kiss on the first date and that is your MO, great. But don't just be like
Googling like what to do on first date. No kissing. Got it. Check. No. If a man is going to treat you
like a piece of shit and isn't going to call you, he's not going to treat you like a piece of shit
just because you fucked him or made out with him on the first night. A man knows. Okay. And guess
what? Stop giving all the man the power. And so should you maybe make out with him. So you stop
wasting your time. What if little
right?
Robbie has got a fucking tongue or that hits the back of your esophagus and you hate the way he
makes out or what if like small lip Sammy is like barely gets a little tongue in there and you're
like, I can't even fucking find we're just hitting teeth. You're probably not going to want to fuck
Sammy, but good to know that you've got it done on the first date. We're maximizing our time. People
you want to not have a two hour date. I'd rather have a four hour date. Quick make out. No, he's
not the one.
I can never see him again. So I can then optimize my time to not have a second date with small lip
Sammy. So we have to be thinking. Okay. We have to be thinking this way. Your friends and long-term
relationships. I would be begging. I would be begging to relive that night with Matt. Oh, push
me up against the wall. Sometimes they do. Let's pretend it's our first date. Okay. You have the
power. You as a single woman have the power to be completely having these romantic nights. And
for yourself, literally believe that it was romantic and then don't call him who cares. Get
a make out, get a make out. Okay. I'm sure you have like six guys on hinge right now. And that
would be willing to take you out next week. And so I think that you should embrace it. And I think
you should just start taking them all down. Not like that, but you know what I mean? Just start
trying, start trying. So first dates, I think it's a win. I think it's a try new places, enjoy the
food. And let me say this,
something that I think is so underrated when it comes to getting yourself out there and enjoying
yourself and dating is like, I love being married. I love being in a committed relationship. I love
Matt. Put that aside. That's not fun to talk about. When I think back to some of the biggest
funnest nights of my life, it was living in New York city. It was going on crazy dates with men.
And it was like me just being in this like reckless time in my life. And so I do think that,
like something you need to think about when you are in the dating world is like,
do it for the plot is not actually that dumb of a statement. Okay. I know it's overused, but like
when I look back so much of my fun nights, even if they did end in tears or heartbreak or whatever,
that's the shit I remember now sitting here in my thirties as a married woman, like what I would
give to like quickly live one of those nights. Well, I don't know because like my back hurts
and like, I don't want to go to the club and sit, but like, I like to like relive it in my head.
You know what I mean? Like you're in that,
that stage right now where you're like going to the club and you're going to the bar and you're
meeting the guy or you're done with the clubs and you're like going to the dinners and you're
getting wine and dine. Even if it's a disaster of a fucking story, the way that you are going to look
back on these life experiences that were so wild, these men that you met, these women that you met
that are, you're just like, how was this my life? I'm telling you guys, don't hold yourself back
from those opportunities because one day when you do find your partner and if you want kids one day
stories you're going to have and the life that you're going to live, it's so much better than
being like, I was too afraid to take that guy out of the dating app or to go up to that guy at the
bar and to actually like make something of it. And so I just ended up sitting and I watched nine
fucking seasons of vampire diaries over and over until I could recite all the lines that will
always be there. All of your shows will always be there. Your books will always be there. Your
comforter will always be there, but like these opportunities won't. And so like sacrifice one
night if you're tired and go out and do something else. And so I just ended up sitting there and
and have the fucking date go for it because I genuinely believe when I look back, what made me
so confident as a woman was a lot of these really weird experiences I went through and some were not
enjoyable. And in the moment I was sleeping in the bathtub, crying my eyes out. I don't know why I
was in the bathtub for dramatic effect, obviously, but think about that. That's how drama I was back
then. I was like, oh my God, I'm single and I'm dating and these men, they're breaking my heart.
I wouldn't, I'm not going to cry in the bathroom anymore. Okay. So it's like allowing yourself to
also be present in what part of your life you're in, allowing yourself to recognize that being
single is such a blessing. It's such an opportunity to learn things about yourself, to experience
things with people, even if they are negative, like you're going to become a stronger, better
person. And I do genuinely believe that there is no fucking way that I would have been ready for a
Kaplan had I not gone through the amount of nights in the fucking Acme basement and Bijou bar and
One Oak and like all of these different places and all the different bars and clubs that I went to
with men and or met men there, what came from meeting those people and the dates and the trips
and all of it. I had to go through all of that to then mature, learn what I wanted, learn what I
hated, learn what I, what I wouldn't put up with, learn certain things on a first date that I'm like,
Oh, that's another flag that that other guy taught me that I know I don't like I'm up. I'm leaving
by, or, Oh my God, I've never felt this way on a first date. This is a good sign. I'm going to do
a second date. Like you learn so much about yourself. And then when I met Matt, I felt like
I knew that first night because I had never met anyone like him. And I had never felt anything
like that before. And I had dated so many fucking losers. I had gone on so many bad dates. I've told
you guys, I think the story of like,
the guy that like literally used me and he was engaged and he just wanted to see like what it
was like to go on a date with the caller daddy girl. And I was like fully there for an experiment.
And I thought I really liked this guy. And then it turned into like, I was getting fully conned.
And I was like, Oh my God, like, this is so embarrassing. Like I've just gone through so
many weird things as you all have, where you can close your eyes and picture all the fucking losers.
But I promise you to find the positive. Sometimes those losers are literally the best thing to
continue to build your backbone.
To continue to build your arsenal of exactly what you want. So when you find your Matt Kaplan or when
you find your whatever, whoever that man is, it's so glaringly obvious. But had I met Matt when I was
22, I would have never been ready for Matt. Cause I wouldn't have appreciated all the amazing things
that he brought to me. Cause I had to go through the fucking dog shit. I had to be like, this man
fucked me over and this man did it. Like, I swear, I swear. It makes me appreciate that 10 times more
that I had all of these like really horrible dates to be like,
thank God I fucking found you. I say that to that man, like at least once a week, like,
thank God I found you, Matt. And the only reason I'm able to say, thank God I found you
is because I found a hell of a lot of fucking trolls underneath the bridge and thought they
were princes. And then they turned out to be Gollum. Okay. And I was like, Oh my God. And I
had to experience that. And you guys do too. So although dating sometimes, listen, it's not going
80% positive dates and 20% negatives. I get it. Sometimes it's 70% negative, but that's also why
finding your partner one day is that much sweeter. The effort that you put into dating, the effort
you put into being single, the effort you put into working on yourself, not self-centering around the
men in your life. You're like, who am I? What do I like? What do I deserve? I have high standards
now. I know what I want. That builds and builds and builds so that the, when you do find that
person, you're ready.
They're ready for you. And you're, you know, what you're ready to accept and what you're not
willing to put up with. And so get out there to all my single ladies who maybe you have been
taking a hiatus. That is so fair. And that's so fine, but do not let yourself continue to get
upset over. Oh, but I see like turn off also social media. That's been the best fucking thing
ever. I like posts. I turn it off. Everyone is so fucking negative. I'm sorry, but everyone's
so negative on social media, giving their thing pieces of why dating fucking sex in 2026. Well,
we're alive in 2026. What are we going to do about it? Be fucking victims and have victim mentality like this sucks so much. All right, we'll get off your
fucking phone and just go and try and try and try and try. Cause I, I promise you something good is
going to come of it. So change your attitude. I'm always here. I'm, I'm literally at the fucking
front lines with you. You are not alone. You've got this. Sometimes we just need to remind
and we're letting ourselves create this negative narrative around something that guess what?
If it was supposed to be so fucking easy, everyone would have perfect relationships and everyone would
be fucking happy and perfect and, and would be a boring fucking life. You need to do the fucking
hard work to actually get something that is worth the fucking hard work. Nothing fucking great is
easy. Okay. You got to work for that shit. Thank you for coming to my Ted talk and to all my single
friends. Get that fucking selfie bitch. Cause I know you're hitting that cut crease. You're
overlining that lip.
a little bit you got that highlighter boom get the selfie if all goes to shit get the fucking
selfie before the first date and tag me going on my first date boom hot bitch love you
all right daddy gang that is it for this week's episode um I hope to god that this inspired some
of you because I a lot of times and I always tell you guys this like a lot of times I just
think from my own perspective of like what would I have needed and although I loved dating and
going out I do genuinely think that I really remember some times where I just really struggled
to be like I think I need a break and again like that's fair but
you
it's almost like right when you're done with it is when you need to just get back at it
get back on the fucking horse and so I love you guys I know it's not easy out there I also know
like men fucking suck right now and it's just like but I promise you there are some good ones
out there and you just have to really fucking look and I know it sucks that we have to be like
digging in the weeds to like find not even a diamond just like you know like a little like
copper metal or like just like a little something but you
you are smart and brave enough to weather the fucking storm ladies so
daddy gang I love you so much and I will see you fuckers on Wednesday goodbye
Podcast Summary
Key Points:
The speaker reflects on her six-year marriage to Matt, emphasizing that being single was a transformative, empowering phase that built self-awareness and independence.
She argues that dating and being single are equally valid and meaningful experiences, and that the early stages of dating should be fun, low-stakes, and centered on self-exploration.
Modern dating apps have reduced spontaneity and emotional connection, making dating feel like a chore and leading to emotional numbness and disappointment.
Flirting in person—especially at bars or social events—is encouraged as a joyful, fearless act that builds confidence, reduces fear of rejection, and fosters genuine human connection.
First dates should be romanticized, not rigidly structured, with advice against strict rules like same-location dates, only drinks, or no kissing.
The joy of dating lies in the experiences themselves—whether fun, messy, or painful—because they build self-knowledge and emotional resilience.
Being single offers opportunities for growth, self-discovery, and learning what one truly values in a partner, making future relationships more meaningful and grounded.
The speaker calls for a shift in mindset
Summary:
The speaker reflects on her six-year marriage to Matt, acknowledging that her time as a single person was just as transformative and valuable as her current relationship. She emphasizes that being single isn’t less meaningful—it’s a crucial phase for self-discovery, confidence, and emotional growth. She critiques how modern dating apps have turned dating into a mechanical, stressful process, stripping it of fun and spontaneity.
To counter this, she advocates for relearning the art of in-person flirting—starting with simple, fearless interactions at bars or social settings—as a joyful, low-pressure way to build confidence and connection. She encourages viewing first dates as romantic experiences, not choreographed tasks, and pushes against rigid rules like fixed locations, drink-only dates, or no kissing. Instead, she promotes spontaneity, fun, and emotional authenticity, reminding listeners that even painful or awkward dates offer valuable lessons.
Ultimately, she argues that the chaos and unpredictability of dating—its highs and lows—create the foundation for strong, self-aware relationships. She urges single individuals to break free from social media, take risks, and embrace the adventure of meeting new people, because the experiences of being single and dating are not just valid—they are essential to becoming the person ready to love deeply, wisely, and fully.
FAQs
No, both being single and being in a relationship are equally meaningful. Being single offers valuable self-discovery, growth, and freedom, while being in a relationship brings connection and partnership. Neither phase is more important than the other.
Dating apps often remove spontaneity and curiosity by turning dating into a chore-like process. They prioritize outcomes over experiences, leading to numbness, high expectations, and a sense of rejection that makes the process feel draining and repetitive.
Enjoying a first date starts with mindset—viewing it as a fun, low-stakes experience rather than a task. Prepare with excitement, dress to feel confident, and focus on having a great conversation, not on meeting specific rules or outcomes.
No, you should not avoid food. Eating is a fun and natural part of a date. Trying new food or sharing a meal helps create connection and allows for more authentic interaction, not just drinks.
Yes, it's okay to kiss if it feels right and natural. The first kiss is a romantic and exciting moment that can be a highlight of the date. Denying it just to follow rules can miss out on genuine connection and joy.
Flirting helps build confidence, creates chemistry, and makes dating feel fun and spontaneous. It's about making someone feel good, not just getting a number or a date, and it strengthens the sense of connection and fun in interactions.
Chat with AI
Loading...
Pro features
Go deeper with this episode
Unlock creator-grade tools that turn any transcript into show notes and subtitle files.