All Episodes

October 22, 2025 • 35 mins

There are no rules when it comes to dating. Tiff Baira, TikTok's cupid and author of the new Modern Dating for Dummies, joins the pod to break down the difference between situationships and flings, healing after heartbreak, and the kinds of dating advice we should ignore online.

 

Do you have a boysober story to share? We'd love to hear from you! Email us a voice note at boysoberpodcast@gmail.com, or leave a voicemail at (518) 83-SOBER. Please say your name before leaving your message, and don’t forget to include your phone number in case we want to follow up. By leaving a voicemail, you are giving Boysober permission and license to use some or all of your message in our show. But if you want to be anonymous, please state that in your call.

See omnystudio.com/listener for privacy information.

Mark as Played
Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:01):
There's not one rule, there's not one way to date.
It's not one size fits all. And like I'm not
here to tell you the rules. I'm telling you how
to work with what you got. So that's like a
big distinction because I think a lot of previous like
dating coaches, matchmakers, they're always if you don't look a
certain way, you don't act a certain way, you don't
give up your whole fucking personality, like you're not gonna
ever find love. And my thing is is like I'd

(00:21):
rather you have less people that really love you for
you than sell out Madison Square Garden of like fake
people that just want you for the wrong things.

Speaker 2 (00:36):
I'm hopewordered and welcome to Boysover, a space where we're
learning and unlearning all the myths were taught about love
and relationships. Today, I'm excited to pick the brain of

(00:57):
our guest, tif Barra. You might know her from her
viral TikTok show streethearts, where she identifies as New York
City's official TikTok Cupid. She's known for being authentically and
unapologetically herself and encourages others to do so too, both
in our everyday lives and in our search for love,
I'm still constantly grappling with how to confidently and authentically

(01:20):
approach this whole boysover.

Speaker 3 (01:21):
Thing, even two years in.

Speaker 2 (01:24):
So I thought a conversation with Tiff was the perfect
way to find some clarity.

Speaker 3 (01:31):
Tiff, welcome to boys Sover.

Speaker 4 (01:33):
Thank you so much help. I'm so happy to be here.

Speaker 2 (01:36):
Let me get a couple of hot takes from you.
Just about like the dating scene right now. Situationships, yes
or no.

Speaker 1 (01:44):
I am against situationships because I think situationships are one sided.
It's one person that actually wants a relationship and one
person that just settling because they're scared that if they
ask for more, they'll lose them. So I'm against situationships.
But I'm pro a fling because fling feels more mutual.

Speaker 2 (01:58):
Okay, yeah, I'm like, what's the biggest differs and how
would you avoid a situationship but stay in a fling.

Speaker 1 (02:04):
A fling is being very upfront about what you want
from the jump and accepting what people tell you as well. So, like,
you can't change a person. If someone's like, I'm not
looking for something serious just by being amazing, You're not
going to change what they want, so I think a
situationship is almost trying to like invest in something that
you'll never get a return in, where a fling, like
a flirty fall fling, is about like, hey, I don't
know where this is going, but I'm okay with that,

(02:25):
and I want to get to know you and that's
my main objective. But if you're telling me like, hey,
I want to have kids by like thirty and I
want to have all do not get in a fling.

Speaker 2 (02:33):
You know, my producers just put it at me, Christina,
what are you thinking?

Speaker 1 (02:38):
Me?

Speaker 2 (02:39):
Well, here's my thing is, I'm telling everyone and myself
that I would like kids by thirty two gorgeous.

Speaker 3 (02:45):
But I don't.

Speaker 4 (02:46):
Are you still boy?

Speaker 3 (02:47):
Sob okay?

Speaker 1 (02:47):
Yeah, because when last time I saw you, you told
me I wasn't dating, and I.

Speaker 4 (02:51):
Was like, come find me when you're ready.

Speaker 3 (02:54):
Here's the thing.

Speaker 2 (02:54):
It's been like such a I was just telling Christina
about this, but like, you know, this whole thing started
two years ago, and I'm a little embarrassed to say that,
Like I still haven't really like done the work I
feel like I need to do. Like the whole point
of going Voysover for me was like creating like deep

(03:15):
connection outside of romance, but I still sort of get
anxious at a party.

Speaker 3 (03:19):
You see what I'm saying.

Speaker 1 (03:20):
Okay, girl number one, don't be embarrassed, Like you're never
gonna be ready. And I think that's a big point
of the book in my whole like philosophy is like
if you wait to be ready to start living the
life that you want, whether it's romantically or in your career,
like it'll never happen. So like I feel like, start
treading the waters of your comfortability. So if you're saying
like I'm starting to get anxious, like I'm not ready

(03:41):
to go out there yet, there's some validity to that.
But then I would also ask you to like reflect,
like what exactly am I not ready for? Because, to
be honest, a date is just being hot and going
to grab a coffee, you know what I mean.

Speaker 2 (03:52):
Well, I was thinking about this because I was having
a chat with my friend and I was like.

Speaker 3 (03:56):
I don't like a first.

Speaker 5 (03:57):
Date, Like I don't like you want a marriage, you
want to skip the dating, Let's get married.

Speaker 2 (04:03):
I'm like I don't want to sit at dinner and
like ask you about your siblings and like do this
whole thing where I have to be very I don't
know where I have and it doesn't really feel like
I'm performing, but I just maybe it's like I'm straight,
but I don't like men, so like sitting at the
table and talking with them, I'm like, oh.

Speaker 4 (04:20):
Have you ever met I've.

Speaker 1 (04:21):
Ever met a guy that you don't know what the
intention is, right, you just met Let's say you met
him at a coffee shop or you were walking and
you instantly just like like chatting with them. Has that
ever happened?

Speaker 2 (04:31):
Yes?

Speaker 4 (04:32):
Yeah, I think bring that energy into a date.

Speaker 1 (04:36):
Like yesterday I met up with someone and I'm like,
you know, I've known him for a long time and
reconnected and we never it was always friend. And my
thing is is like anyone that I'm going to date
has to start as a friend because like to me,
throughout all my breakups in my life, I don't miss
them as like a lover because most of the time
they're not that good. But what I miss the most

(04:57):
is that friendship.

Speaker 4 (04:59):
Is that bond.

Speaker 1 (05:00):
Is that person that like is there for you when
you're having anxiety, That person that believes in you more
than you can believe in yourself. So I think to me,
if you're saying like I don't want to go through
the interview process, then don't you know? And also don't
force yourself to, Like I LOOKK you have like a
fifteen minute rule. If I'm sitting on a date with someone,
I know in fifteen minutes if I want it something more,
whether that's like something long term or a fling or whatever.

(05:22):
So if I know in fifteen minutes whether I like
someone or not, why the fuck am I going on
an eight hour date and putting on a performance? Because
a lot of times you could just be funny and entertaining,
but you're just like you're like was a day good?

Speaker 4 (05:32):
Or am I just like so fucking funny?

Speaker 1 (05:34):
You know?

Speaker 4 (05:36):
So if you feel like you're performing, get out.

Speaker 2 (05:38):
I want to know how you came to have this philosophy,
Like have you always been this sort of like sure
of yourself or like knowing what you want and don't want?

Speaker 4 (05:49):
No, I've been deeply insecure my whole life.

Speaker 3 (05:51):
Tell me about the process. Yeah getting there?

Speaker 1 (05:53):
Well, I think I'm still in it. And to your point,
I don't think you arrive at confidence. I don't think
you arrive at being ready to be able to be
like the hottest confidence person in the room. I think
there's moments and I think you start feeling like your
better self when you start telling yourself and giving yourself
what makes.

Speaker 4 (06:09):
You feel like that person.

Speaker 1 (06:11):
So, for example, I know now like I'm not gonna
be I'm gonna not gonna feel good if a guy
is taking eight hours to text me and I don't
deserve that right. So if I start seeing that, I
don't view that as like, oh, he's just busy. I
view that as like, no, that's disrespect. It's not an alignment.
Onto the next I'll communicate it. So your job is
not to expect everyone to be in alignment with how
you live. But after you communicate what you need, they

(06:32):
either have the choice to accept or reject that. But
don't sit there in that rejection and expect them to change,
because that's how you become booboo the cloud. You're like,
why am I like waiting by the phone waiting for
someone to text me when I should be out.

Speaker 4 (06:43):
With the girlies. It's because you're choosing to do that.

Speaker 1 (06:46):
So I've grown stronger and knowing that, like, people will
show you who they are, and you have to choose
yourself over the wrong person, no matter how hot they are,
no matter how great they are on paper, because someone
that is really interested in you and wants to show
that you'll know. And I think like it's all about,
at least for me in my journey, understanding that I
deserve it because I've had people that tried to love

(07:07):
me and I wasn't ready to be loved because I
was used to toxicity for a long time.

Speaker 2 (07:12):
What does your dating life look like right now? Are
you on the apps? Are you just noticing people at parties?
What's going on?

Speaker 1 (07:18):
I went through like a really long breakup and it
took me a long time to heal because I think
going through a really long term relationship made me realize
a lot of things that I was neglecting in myself
and expecting someone to fix. So instead of jumping into
someone new, I really took the last seven months to
just be alone like I haven't And I think it's
so important to not rushshelf to date until you're ready.

(07:40):
That's why I love you know what you do or
you know whatever you're doing. You have a lot of
like autonomy, and I really respect that, Like I think
that's great and it takes a lot of strength and power,
but I did that and then I feel like I
ran into him, cried, and then I felt healed because
the same night I met someone that I felt like,
oh that could be put maybe if it's not him,

(08:00):
he's an example of what my future could look like.

Speaker 4 (08:02):
So I closed the chapter.

Speaker 1 (08:04):
And since then I'm dating. I you know, I go
out not looking for anything, but I really like.

Speaker 4 (08:11):
Meeting in person. I am on the apps, but like,
I love that.

Speaker 1 (08:14):
Like cosmic attraction, when you like run into someone and
you just like each other stuff.

Speaker 4 (08:19):
Of course, yeah, I'm dating. I'm dating to day around.
I'm not married yet. Yeah, if you're single and silly
was doing?

Speaker 2 (08:28):
I want to know what sort of your seven months
of healing looked like? Yeah, would you say it was
like very intentional? Would you have considered yourself kind of
boys sober?

Speaker 3 (08:36):
Were you like dating at all?

Speaker 1 (08:37):
Like?

Speaker 3 (08:38):
What did that look like?

Speaker 4 (08:39):
A lot of pilates and a lot of tears. I
swear to fucking got it.

Speaker 1 (08:44):
And one day I'd be like, I don't need him,
I'm not bitch. The next I'm like, oh my god,
who am I without him? Like I'll never heal? Healing
is turbulent. It's like being on a spirit airline in
the middle of a thunderstorm.

Speaker 4 (08:56):
I feel like it's been.

Speaker 1 (08:58):
Very chaotic, and I've been really like to be able
to like share some of that because I think there's
so much strength in understanding that, like a breakup won't
break you, even though you feel like it. Being in
love with someone that knows every single thing about you
and then learning how to be on your own again
is truly just traumatizing, but it's gotten a lot better.
So I think for me, the last seven months have

(09:18):
been about Number one, what are the insecurities that I've faced.

Speaker 4 (09:22):
Before him and that I'm still facing now without him.

Speaker 1 (09:26):
You know, I struggle a lot with like my body acceptance,
my self talk, imposter syndrome. I mean, I still struggle,
and I think what is really exciting is that at
least I'm struggling and haven't given up, and I don't
make it make me bitter like I would rather. You
can't lose if you don't quit, And I feel that
way about my insecurities, so I don't expect them to

(09:48):
go in away anytime soon. Like some mornings i wake
up and I'm like, oh, Umshrek's toe, and then the
other morning, I'll be like, oh my god, I'm a
bad and I think we've had a lot of rhetoric
that's been like too be a bad bitch.

Speaker 4 (10:01):
You have to be confident all the time.

Speaker 1 (10:02):
That's not the case, right, Like we're both like there's
so much love around you, and I think when you
do decenter the wrong person, expect the next six months
of your life to be kind of like hillacious in
the sense that like you'll have moments of great like, Wow,
I'm doing it on my own, this is amazing. None
of my healing has ever been about him. It's been
about knowing that I will still be standing after him

(10:25):
and after the next breakup, and after the next breakup,
all you have is yourself. But I can't go into
my next relationship hating some of the things I hated
about myself while I was with him, you know, So
that breakup time is really pivotal, and I feel like
I've gotten to learn myself a lot more because I'm
looking to have fun right now. But I don't want
to have fun with people that I don't see a
potential with.

Speaker 2 (10:45):
Tell me, yeah, tell me about when you really started,
like your public journey, did it start sort of with
like dating, advice, matchmaking things like that or was it
another No.

Speaker 1 (10:54):
I started being like, here's where the metals with bachelor's
because that's where I was.

Speaker 3 (10:58):
Oh, that's where I was.

Speaker 4 (10:59):
I was going out to meet men, and like I
loved it.

Speaker 1 (11:02):
And I think, like, honestly, I still like going to
a bar and flirting with the hot guy totally, that's all.
I don't want to be right, you know what I mean.
But I think what's interesting now as I've grown, is
like now I match them from a place of power.
It's like, oh, you're a dick. I don't give a
fuck it out of my face. I'll buy my own drink.
I don't want to time right at that point, I

(11:23):
remember I was like sneaking in Smirnoff ice and water bottles,
like to the bar because I can't afford you know,
classy trash. It's always what I what I like to do.
But I think, like I wish and I hope for
this next. Like what I love about TikTok. You hear
so many people's different opinion and then it can be
really toxic. But there's also if you can find that

(11:44):
like comfortability circle, just like someone that helps you remind
yourself that you're deserving and that there is love out there,
because I think we hear a lot of all men suck,
there's no one good left, and I like to think
there are always going to be good people. We have
to reject the negative pieceeople that are blocking you from
the good people.

Speaker 5 (12:02):
Don't let your fuck boys stop you from your husband.
And that's what I like to you know, show on
my page.

Speaker 2 (12:08):
Yeah, I like, I feel like you potentially were born
with matchmaker energy.

Speaker 1 (12:13):
Like were you like on the playground?

Speaker 4 (12:17):
I yeah.

Speaker 1 (12:20):
When I was a kid, my parents were divorce when
I was six months old. I never saw love except
for on TV, and like, what the fuck is that?
Like it's just random people meeting in a grocery store
and falling in love and kissing in the rain and
they're married forever.

Speaker 4 (12:31):
That's not realistic.

Speaker 1 (12:32):
So I always wanted to match make my parents and
I would like do schemes to get them back together.

Speaker 3 (12:36):
Tell me about some scheme.

Speaker 5 (12:38):
Scheme.

Speaker 1 (12:38):
Tell me I'd like pretend to get sick at school
and get them to call both of my parents to
come pick them up, Like bitch, I was flotting that
is yeah, No, I was going on.

Speaker 4 (12:47):
That's amazing, and I would sabotage who they were.

Speaker 3 (12:51):
You're lying, I was your parents?

Speaker 2 (12:53):
Good for you?

Speaker 1 (12:54):
Girl? Right?

Speaker 3 (12:56):
Did it ever work?

Speaker 4 (12:57):
But you can't blame the girl for dry of course.

Speaker 1 (13:01):
But yeah, I think like truly as someone that was
always on the outskirts of being desirable quote unquote, like
since I grew up, I was always knows like the
fact girl right. And I think this also shows for
a lot of like queer relationships, you don't have a
lot of exposure to what that relationship looks like because
in entertainment's always tropes you have like the gay best

(13:22):
friend or hyper sexualized queer communities, which is not the case.
So when I created Streethearts, my goal was to show
real people just being themselves, yapping and seeing if there's
a connection, because I know what it was like to
be lost and be told by like Patti Zanger, like
from a million dollar matchmaker, that if you are not
a size too, no man will like you, and if
you have an opinion, no man will like you. And

(13:43):
I'm the antithesis of that, amplifying that representation of not
just tropes and more of like real people is what
I hope the future of entertainment. But also the dating
space is so important as young kids are learning how
to date, like you know, eighteen twenty, you feel like
if you don't look like person in the magazine, that
you don't deserve love.

Speaker 4 (14:02):
So there's almost this.

Speaker 1 (14:03):
Like amazing ability now with TikTok to show different people
and I really hope that, like, even if it's just
like someone understanding that, like they can be themselves by
watching Streethearts or reading you know, modern Dating for Dummies.
It's like there's a place for you even if you
haven't seen it yet, it exists.

Speaker 2 (14:38):
What is like a piece of advice you see circulating
online that you think is like the worst piece of
dating advice.

Speaker 1 (14:45):
Oh, I really hate the rhetoric that like men only
like they call it your feminine energy completely. I feel
like that's just another blanket statement of saying a woman
that doesn't have an opinion or only placates men. If
you're naturally soft spoken and like someone to lead, I
think that's great, But also there's a difference between someone

(15:06):
leading you and owning you. And to me, if you
like when a guy orders for you at the restaurant.
That's great, but a guy that actually cares about you
will ask what your favorite type of food is or
will ask like what area is comfortable for you. I
hate this binary of like alpha male and woman. That's
like just wanting to be that again. If that's what
you want, great, but make sure that you're being respected

(15:28):
through it. Like in high school, towards my mid twenties,
I felt like guys would only like me if I
watered myself down. So I think that advice is really
shitty because yes, you can get the millionaire with the Bugatti,
and you know, like, if he doesn't love you and respect,
you're gonna feel like you're in a trailer park.

Speaker 4 (15:46):
So that's my advice.

Speaker 1 (15:48):
Don't don't chase the person on paper, and don't water
yourself down for the wrong person because you think that's.

Speaker 4 (15:53):
All they'll like. Especially I can go one last come on.

Speaker 1 (15:58):
The worst advice that I've ever heard is that guys
only like one certain type of body, and I think that's.

Speaker 4 (16:04):
Really created just generational trauma is so many people, and
it's not just for women.

Speaker 1 (16:09):
I also think it impacts all genders in a sense
that like no matter who you're sexually attracted to the
idea that there's.

Speaker 4 (16:16):
One body that someone likes, it's not the truth.

Speaker 1 (16:19):
You know, you're so much more than your body, and
so much love you more than just your body, because
those types of people that only like I for your
body are the same type people that might cheat on
you when you get pregnant. You know what I mean, right,
So let's go a little deeper. That's what I of
course you know, and I think it's it's really important
for young people in general. Like sex can be a
band aid on a bullet wound, right in the sense that,

(16:40):
like you get a dopamine hit of what affection feels like,
but that's not affection.

Speaker 4 (16:44):
That's at tension.

Speaker 1 (16:45):
And I think it's so important to make sure that
everyone dating, whether it's just to have casual fun, you
feel empowered by it and it's liberating, but you're not
sleeping with someone in order to hope that they'll love
you more by doing it, Because I think that's something that,
especially when you're younger, you get lost in because you're
experiencing all this for the first time, and a lot

(17:06):
of times, if you do struggle with insecurities, you tell yourself, like.

Speaker 4 (17:10):
This is the best I can get.

Speaker 1 (17:11):
So my whole new approach as I've grown older and
really proved to myself that like, honestly, it's better to
be alone than with the wrong motherfucker, and I practice that,
and I think it sometimes takes leaving what you've always known, resetting,
do a whole metamorphosis, like pause your subscription.

Speaker 4 (17:29):
Get in the cocao, get in the cocoon.

Speaker 1 (17:31):
I feel like every few years I get in the
cocoon totally, and I'm like, because I want to come
out a better version of myself and not for anybody else.

Speaker 4 (17:36):
And that's why I like, you know, I always.

Speaker 1 (17:40):
Feel like being bullied, broke and confused it is the
best thing that ever happened, because I feel like, in
a way, like I've realized I when I was like
eighteen to twenty five, I thought I was going to
have the picket fence and the Prince Charming, but the
American dream guys sometimes in an American nightmare.

Speaker 4 (17:55):
Right and if American psycho.

Speaker 1 (18:00):
But uh, for me, I'm still in this process of
learning to love myself. But I'm gonna give myself everything,
and I want to date out of desire not desperation.

Speaker 2 (18:09):
And what would you say to that person who feels
like there's not a place for them but they like
want desperately to step out or step into a relationship,
Like what's that first step look like?

Speaker 4 (18:20):
So people are gonna talk shit? Yeah, I trying to
get fair warning right right.

Speaker 1 (18:28):
Being who you are will never be without people putting
you down or talking shit.

Speaker 4 (18:33):
But they're gonna do that either way.

Speaker 1 (18:34):
So to me, I would say, find out what makes
you happy, whether it's like I mean, I'm wearing clown colors,
I love to wear bright colors.

Speaker 4 (18:42):
I like to do that.

Speaker 1 (18:43):
I like to I might be too loud to some
or I might be too opinionated to some, but you
have to go inward. So I would say, like, if
you're just starting to date, no matter your age, whether
that's post divorce or you're just first college relationship, write
down like what.

Speaker 4 (18:55):
You like about you?

Speaker 3 (18:56):
Do you like to bold?

Speaker 4 (18:57):
Do you like to go party all night?

Speaker 5 (18:59):
Like?

Speaker 4 (18:59):
Whatever that is?

Speaker 1 (19:00):
Because you're not looking for someone to complete you, You're
looking for someone to reflect you in certain ways. So
how the fuck are you gonna find someone to love
You don't know what you love about yourself?

Speaker 4 (19:08):
So get a pin and paper, write it down.

Speaker 2 (19:11):
I'm like, this is another thing I'm gonna put into
my brain forever.

Speaker 4 (19:15):
I got you.

Speaker 2 (19:16):
I loved your quote. How you date is how you live? Yes,
can you just tell me about the inspiration behind that?

Speaker 4 (19:22):
One hundred percent? Again?

Speaker 1 (19:23):
As a deeply insecure baddy for most of my life,
I realized that, like, I.

Speaker 2 (19:27):
Wait, totally a deeply insecure baddy. I like, yeah, no, right,
because you have to like come out of that and
it's all I just like those two together because it
proves that it's always within you.

Speaker 4 (19:39):
Oh yeah, no I am.

Speaker 1 (19:41):
I'm not sitting here to say like, oh I took
a magic potion in it's a confident. I literally have
cried in the back of the uber this last month
about not feeling good enough, and I'm sure I'll do
it again, right, But what I will say is that
how you live is how you date. It embodies two things.
It's the narratives that you tell yourself. So the same
way that you say, oh my god, that pers is
out of my league is the same way that you're

(20:01):
gonna say that job is out of my league, or
the same way that you say, like they could get
that guy but I couldn't. That's same way that you
say they could pull out that outfit but I can't.
So rather than telling yourself and limiting yourself, whether that's
in dating or in life, it's all the same because
if you limit yourself in one thing, you're gonna still
have those those thought processes and limits in everything you
do of course. So I mean I think, like, in

(20:22):
my opinion, shoot your shot, figure it out, So like
how you live is how you date to me, means
like shoot your shot with a person, a job, a career.
And also, don't let other people tell you that you
have to live by their rules. So you know, no
matter who you're attracted to, do, no matter where you
want to live, no matter what it is like, play
by your own rules, do things on your own terms.

Speaker 4 (20:42):
And if people talk shit, let them give them some entertainment.

Speaker 3 (20:45):
Right, give them something to talk about. Yeah.

Speaker 2 (20:48):
No, I'm resonating with this because I've never thought about
it that way, how you live and how you date.
But it makes a lot of sense as someone like
We've been talking about this a little bit, but I
haven't totally explained and like, yeah, am I still boy sober?

Speaker 3 (21:02):
What's going on? With me there, I am trying.

Speaker 2 (21:05):
To be still and sort of like re entering the cocoon,
like we were talking about trying to like not have
sex with men because it makes me crazy.

Speaker 4 (21:13):
Okay, why does it make you crazy?

Speaker 3 (21:15):
Thank you for asking?

Speaker 4 (21:17):
I mean, girl, I probably really.

Speaker 2 (21:20):
I think it makes me get too attached and to
emotional and I've found out that my attachment style is fearful, disorganized.
And this is like when you want someone close to you,
but then as soon as they are close to you,
you push them away.

Speaker 3 (21:33):
And then you're like in this loop.

Speaker 1 (21:34):
Do you feel close to other people in different senses
other than sex where that brings that same feeling?

Speaker 5 (21:39):
Right?

Speaker 3 (21:39):
Totally.

Speaker 2 (21:40):
I think sex is a really easy way for me
to feel connected, Okay, Right, And it's like you sort
of said bandaid on a bullet wound, and I think
it's like a really simple way to feel like you're
close to someone because.

Speaker 4 (21:50):
I'm an emotional slut.

Speaker 1 (21:52):
Right, I could not have sex with someone, and like
I could have sex with somebody like, oh good riddance. Right,
have a great rest of your life, sir. But if
I have a martini and spill my whole life to
someone else, right, my husband, right right, vulnerable. But I
think that it's so interesting that, like to your point,
you can define it how you want, right, like when
I'm emotionally slutty and I'm like.

Speaker 4 (22:11):
I do not know that man's middle name. Why does
he know everyone that's ever hurt me in my life? Yeah?
So so it's more the physical is what makes you crazy? Yeah, yeah,
you're not crazy, You're just passionate. But I was in entile.
Don't ask me about it. I don't be on your side.

Speaker 2 (22:28):
But I guess I want to know, like, do you
think I should be dating or do you think I
should just like really not even date sort of in
this like re entering a cocoon era, like in your
healing era, were you going on dates or it was
just pilates and tears like you were saying.

Speaker 1 (22:44):
So, okay, I have a few questions before I answer
your question, but I will say in my experience, I
went on like two or three dates. One date was
like eight hours, so amazing. I love this man, and
then he ghosted me and still likes every single one
of my Instagram stories. Annoying, I mean, like, but to me,
I don't take it if it's like okay, like you're
a fan, Like like I'm okay, Like I people'll show you.

(23:05):
So what I always say is like I went on
like three or four dates in the seven months.

Speaker 4 (23:09):
Now I've been on like three days this.

Speaker 1 (23:11):
Week, because it's like ebbs and flows, like I feel
good and when I feel good, I'll date when I
feel good, and then if I don't feel good and
I want to be in cocoon. Fully, I hate this
idea that you have to be one way, like the
clean girl that does pilates and then like only.

Speaker 4 (23:25):
Drinks green juice.

Speaker 1 (23:25):
Like you could be a girl that doesn't have sex
for six months and then has sex every day.

Speaker 2 (23:30):
For the week.

Speaker 4 (23:31):
There's protection, and or you could be someone that works
out all the time and doesn't you know. I think
my advice.

Speaker 1 (23:37):
For you only you know when you feel good, right,
and don't force yourself or put pressure on yourself to
either stay boy sober or to not because of what
other people think or the judgment that you have on yourself.
Because I think a lot of times we carry the
baggage of like resentment and disappointment, and like how we
can be so hard on ourselves And I'm really bad
at that I'm a perfectionist. I would never talk to

(23:59):
my friends away that. Sometimes I talk to myself, of course,
And I think all I could say to you is that,
like you deserve to be in control of your dating life,
feel happy and empowered by doing it. So if you
call me tomorrow and you're like tiff, like I'm.

Speaker 4 (24:12):
At a guy and I want to sleep with them.

Speaker 1 (24:14):
Great, right, And if you do it and then you
don't feel good about it, reassess what went wrong? What happened, Like,
how do I move forward from there? I honestly think
we're just in like the dating lab, Like we're a
little nice trying to find like what works. Like it's
a lot of experimentation, and I think you're really good
at not labeling what that means. And I think just
having grace on yourself and saying like I'm gonna do

(24:35):
what I feel today totally, and while you do these
life goals of like having a kid by thirty two,
I think also keep that as an alignment measure. So
like if you go on a date with someone and
this is where I say, it's like this weird, it's
a tension because I want you to have fun, but
I also don't want you to forget where you're going.
So it's like you want to drive the cool car,
but you have to remember where you're driving to or else.

(24:57):
To just be in circles and a car without a
destination was point. So I think, like in my opinion,
date people that respect you. It's always that, that's always
the baseline, because I used to date bad guys that
are like tattooed and like I'm different, Like honestly the
summer I turn pretty. Don't date a connor, like.

Speaker 4 (25:14):
You know, I know he's I know he's great, but
all he does is just jerks around and don't be jerked.

Speaker 1 (25:21):
Around right while he might be misunder shit, he has
to do internal work and you can't wait. You can't
pause your life for someone else to do the internal
work that you seem to actively be doing. So like
I would say, try if you feel ready, and when
I say ready, start small flirt with someone that you
think is cute, that's been in your DMS. Maybe go

(25:41):
for like you don't have to do. Don't call it
a date like.

Speaker 5 (25:45):
Networking and what I love aving twenty eight, it's a meeting.
You bring him aden it's a write off if it's
a networking So maybe you don't start dating, start networking, right.

Speaker 4 (25:56):
Build that LinkedIn.

Speaker 3 (26:13):
Talk to me about.

Speaker 2 (26:14):
Choosing, like I choose people who are unconventional. I maybe
choose people who I know are not going to be
long term. You say, like, what's the point of a
car without a destination. I'm usually doing circles in the doughnut.
I don't have the parking lot.

Speaker 1 (26:30):
Do you have fun or do you feel like most
of the time you're anxious and you're like freaking out
about like what's going on?

Speaker 4 (26:34):
Because that's the difference.

Speaker 1 (26:35):
That's again going back to a fling versus situationship, Like.

Speaker 3 (26:39):
I love a situationship. That's my week, Like I get
into it.

Speaker 4 (26:42):
Or the one that wants them more, they want you more.

Speaker 2 (26:44):
Uh, it is whatever the opposite of what they want.
So if they want me more, then I'm like running,
And if they don't want me at all, then I'm.

Speaker 3 (26:51):
Like running, please please.

Speaker 4 (26:53):
Yeah.

Speaker 2 (26:53):
So I'm like always stuck in this loop, which is
the thing I'm like really trying to walk away from personally.

Speaker 1 (26:59):
Do you like that because there's sense of like protection
in a sense, like when you're chasing, you know you'll
never have them, and then when you're protecting you know
they'll never have you, right. So I mean, like, have
you ever been with someone and really felt like they
were your person? You know?

Speaker 2 (27:15):
Like I had one long term boyfriend who definitely taught
me about love in a way that I hadn't really
like experienced before.

Speaker 3 (27:23):
He was like.

Speaker 2 (27:26):
He was like the embodiment of All About Love by
Bell Hooks.

Speaker 3 (27:29):
It was like everything about him. I was like, oh
my gosh, he does this, he does this, he does this.

Speaker 4 (27:32):
Probably before rely read that on the subway right weirdly.

Speaker 2 (27:36):
Like I think he just had like stable parents totally,
and so he was like a really amazing person.

Speaker 3 (27:44):
But I never felt at ease.

Speaker 2 (27:46):
And I was like, if I could love him, if
I could marry him, it would make sense. My life
would be so easy. It could just like all, you know,
But he wasn't my person.

Speaker 1 (27:55):
And I think that's such a great point that you
bring up, because sometimes it could be the person that
you feel like you should love but you don't, and
like they could be treating you really well, but there's
also that magical moment where you feel connected in a
way that words can't even define. So I feel like
respect and excitement and fun. Like respect is the baseline,

(28:18):
but it's not enough in the sense that like a
nice guy that like respects me is obsessed with you,
but you don't feel that spark. That's still not enough,
you know. I think, like, in my opinion from what
I'm hearing from you, you really are.

Speaker 4 (28:33):
You're a lover girl. I feel it. I feel it.

Speaker 1 (28:36):
But what I feel is that like I feel like
I'm like reading your taro.

Speaker 4 (28:44):
No no, no, I'm not a dog do.

Speaker 3 (28:46):
All I'll say.

Speaker 1 (28:47):
Is that I feel like there's some fear into like
actually being vulnerable with someone, which I experience a lot too,
because when you hand over the keys to your heart,
they can fuck your shit up. And I think, if
you've worked so hard to create something for yourself and
that stability for yourself, maybe from a past that wasn't
always stable, it's terrifying to have someone in and to

(29:07):
give them access. So I think, like, if I could
tell you one thing is that, like whoever you want
a date is out there, but it's not gonna find
you In this podcast.

Speaker 5 (29:18):
Maybe it might, but it's not gonna find you working.
It's not gonna find you.

Speaker 1 (29:22):
You know, you can't door dash love like I would say,
like experiment with some of the people that you naturally
gravitate towards.

Speaker 4 (29:29):
So like, do you have passions like outside of work,
Like what do you do?

Speaker 5 (29:32):
Oh?

Speaker 2 (29:33):
Well, I love to dance? Okay, I love that. Yeah,
I'd love like find a lover on the dance floor.

Speaker 4 (29:38):
I don't know about New York class, I don't know,
but it's so cool.

Speaker 1 (29:42):
Like go to dance, Like I mean, I feel like
the main thing is like chasing activities that you're gonna
naturally meet single people at or doesn't because I feel
like Also, like what I hear from what you were
saying is like it feels like a job kind of
like an interview to like go out and physically.

Speaker 4 (29:57):
Put yourself out on dates.

Speaker 1 (29:58):
So what if you could transform the dating experience into
something that you would just naturally do?

Speaker 2 (30:03):
Right? Totally Okay, I'm writing this down. That leads me
to my next question, which is, like, what is your
number one piece of advice for people who are dating.

Speaker 1 (30:12):
I think the number one piece of advice for people
that are dating is to not put your dating life
on someone else's timeline just because all your friends are
getting married and like go into punk me and patches
with their significant others and like kissing in a fucking
like holiday Hallmark fucking movie that doesn't have to be you,
And don't trust everything you see online as true love.

(30:33):
A lot of times, the real connection, the real work,
happens when there's no phones. And I think a lot
of times, like every time I open my fucking Instagram store,
another fucking person's engaged and I'm like, damn, Like I
just like kissed the guy in a.

Speaker 4 (30:45):
Band, Like what's going right?

Speaker 1 (30:47):
I also know that like I would rather be alone
till I'm forty five and find someone that is perfect
for me, then to settle too soon because of fear
that there's no one else left. My biggest advice there
are people out there do the work to be open, vulnerable.
You can't control what happens, but you can control if
you're putting yourself out there. And one of my favorite movies,

(31:09):
He's just not that into you, that big scene where
she's like, I'm a lot closer to love than you
because she's trying. While she was a little anxious about it,
she was trying. So I think it's cool to try.
I think like this whole like I'm too good for love,
like I'm all about my business. Like if that is
you go off like I love a business, battie. But
I also like, I think you can have everything that

(31:30):
you want if you're working actively towards it. And remember
there's different seasons for it. So like if you just
gotta break up, don't feel the need to go shake
ass the club and break up with guys if you're
not ready for it. But also like, once you heal
or whatever healing looks like for you, don't let anyone.

Speaker 4 (31:46):
Tell you what your love life looks like. You know,
and build it for yourself.

Speaker 1 (31:51):
You're literally building your own house, building their own infrastructure.

Speaker 4 (31:53):
You are the architect, the resident. You are everything. And
I always say my biggest thing, you are the bouncer
of your own love club.

Speaker 1 (32:02):
Right and kick anyone out that's fucking around with you,
because that truly is it steals your energy from people
that actually would appreciate it. You don't need to give
a PowerPoint presentation to prove your worth. You don't need
to chase someone that's running away from you. The biggest
question to ask if you're dating someone is what I
like this person as a friend Because we put so
many exceptions and caveats and excuses when it comes to

(32:22):
romantic love, but truly romantic love is just blatonic love
with sex. So I have nothing else to say.

Speaker 2 (32:30):
No, I know, And a lot of times I'm dating
someone or sleeping with someone who I'm like I would
never be their friends.

Speaker 4 (32:38):
You don't have to judge yourself for it.

Speaker 1 (32:40):
And I think like part of it, like I'm giving
all the like woo woo wisdom shit, But also there
is something so valuable and so fun about running around
the city kissing guys learning, Like I think, like there's
a beautiful world where like you have fun, you learn
who not to date so that you can be ready
for who you want to date. But at the end
of the day, like when you're talking more seriously, which

(33:01):
you say you want kids and whatever that structure looks like,
don't think, oh my god, he's the hottest guy in
the world, but he like has twenty other girls on
his rostering streaming like shit, think like would this person
be there for me if my grandparents died?

Speaker 4 (33:13):
Will this person be there for me? If I got sick?
Would this person be there for me?

Speaker 2 (33:17):
You know?

Speaker 1 (33:18):
And knows different capacities because you're not looking for like
the hottest guy that looks like a GQ cover. I
mean that'd be great personality you like the Shreks.

Speaker 3 (33:29):
Yeah, yeah, the same.

Speaker 1 (33:32):
But what I'm saying is like, you want someone to
multi facet in and someone that gets all sides of
you and you know, shouldn't have to feel you're performing.
And when you meet the right person, just like friendship,
you'll have that ease that that makes you feel instantly comfortable.

Speaker 2 (33:44):
What is the biggest thing you've had to unlearn about dating?

Speaker 4 (33:48):
I had to learn that I'm datable. It's all for me.

Speaker 1 (33:51):
I mean, I spent most of my life telling myself
I didn't deserve love, that no one was gonna love me,
and that I truly was someone that they should be
embarrassed about because of like my body or how I
viewed myself. So the last I would say, like ten years,
has been every day showing up and loving myself the
way that I hope someone will one day. I mean,
I really want to find love, and now I'm getting

(34:12):
closer to understanding what that actually looks like for me.

Speaker 3 (34:16):
Well, thank you so much, coming on, You're brilliant. I'm
not kidding. I'm like, I'm gonna journal after this, and.

Speaker 1 (34:24):
I really want to hear and stay updated. I'm always here,
let me know. I will let me know what's up.

Speaker 2 (34:30):
I'll I wish I could hire Tiff as my personal
dating coach.

Speaker 3 (34:39):
We should definitely have her back on for more dating advice.

Speaker 2 (34:42):
But until then, I'm gonna have to go out in
the world, stay true to myself and figure out what
it really is that I want. And I hope that
Tiff has inspired you to do the same. Thanks for
listening and I'll talk to you all next week.

Speaker 3 (35:08):
Boys Sover is a production of iHeart Podcasts. I'm your host, Hopewordard.

Speaker 2 (35:13):
Our executive producers are Christina Everett and Julie Pinero. Our
supervising producer is Emily Meronoff. Our assistant producer is Logan Palau.
Engineering by Bahid Fraser and mixing and mastering by Abu Zafar.
If you liked this episode, please tell a friend and
don't forget to rate, review, and subscribe to Boys Sober

(35:36):
on the iHeartRadio app, Apple Podcasts, and wherever you get
your favorite shows.
Advertise With Us

Popular Podcasts

Stuff You Should Know
Crime Junkie

Crime Junkie

Does hearing about a true crime case always leave you scouring the internet for the truth behind the story? Dive into your next mystery with Crime Junkie. Every Monday, join your host Ashley Flowers as she unravels all the details of infamous and underreported true crime cases with her best friend Brit Prawat. From cold cases to missing persons and heroes in our community who seek justice, Crime Junkie is your destination for theories and stories you won’t hear anywhere else. Whether you're a seasoned true crime enthusiast or new to the genre, you'll find yourself on the edge of your seat awaiting a new episode every Monday. If you can never get enough true crime... Congratulations, you’ve found your people. Follow to join a community of Crime Junkies! Crime Junkie is presented by audiochuck Media Company.

The Breakfast Club

The Breakfast Club

The World's Most Dangerous Morning Show, The Breakfast Club, With DJ Envy, Jess Hilarious, And Charlamagne Tha God!

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.