All Episodes

April 17, 2025 15 mins

B shares her take on dating during the "in-between phase." That space between raising teenagers and the empty nest of kids at college. PLUS: Thinking about what YOU bring to the table and how men can be even more emotional than women. 

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 (00:12):
People talk about midlife crisis, people talk about empty nester.
What people don't talk about is the bridge in between.
And it's a critical bridge and only someone of a
certain age understands this bridge. You cannot explain it. You
have to go through it. What does it mean? You're
one of the guys that I meet. They're good looking,
they're successful, they are wealthy, they're in shape, they're brilliant minded.

(00:38):
Their kids are fourteen fifteen, so they are sitting in
a holding pattern. Now they're single. They want a date.
They can see the end of the tunnel. You have
kids that are thirteen, fourteen, fifteen, sixteen, Okay, they're going
to go to college, but in this moment, they're in
purgatory because you don't know exactly what your purpose is.

(00:58):
Your kids don't really need you. You could go out
of town for a week. They don't really care. They've
got their homework, they've got their sports, they've got their friends.
They can cook for themselves, clean for themselves, organized for themselves,
pack for themselves, plan for themselves. They understand their calendar,
and they are fully functioning beings, which is why in
Shakespearean times they were getting married. Okay, so they are

(01:19):
humans that make decisions and are almost adults, so your
identity is not tied to them anymore. Maybe your kids
have gone off to college. You're a fifty five year
old man, you're a fifty four year old woman, you're
fifty one. You are not yet an empty nest syndrome,
So you don't know what decisions to make because you
are aware of the fact that in two three years

(01:40):
you could live in Florida, you could go to France.
Your kids are going to college. You know that right
now they barely need you, and you could go to
France now, but you still have to be home, and
you have to be a functioning individual in your home,
and you're going to take your kids on the college
tours and you go into the softball and soccer and
lacrosse games like so you still have to be here
in body, but you just basically a driver, housekeeper, errand doer, concierge,

(02:06):
planner atm machine. So you're in this purgatory bridge phase.
So you think the decisions you're making like you're going
on a date with someone. You're like, yeah, I yes,
I do live right now in Des Moines, but in
two years my kids will be gone. I could live
anywhere I want. I can live into loom in Saint
Barts or Africa. You're trying to like make decisions. In addition,

(02:27):
you're kind of purposeless for that same reason you're working,
but like you have more free time. You kind of
know where you are in your life, and you're just
sort of like this body scarecrow that's just putting your
arms in different directions to like direct people where to
go and what to do. You're just waiting till you
get to live your own fucking Ramona Pino Grigio. Move

(02:47):
down to Palm Beach, Boca tennis, pickleball, golf club lifestyle. Right,
that's what it is, you know. Or you're taking your eat,
praying and loving, or you're painting like it's a per
Tory Bridge phase that people don't discuss enough. And people.
I know this because I'll meet men that are like
so successful and they can do whatever they want. But

(03:10):
but I got this, you know, fifteen year old sitting
here that hasn't gotten to where he's gonna be yet.
So I'm here for this, I'm here for the sports,
and I'm I'm in the same fucking boat. I have
this Neppo baby caviar eating freeloader that'll be upstairs at
three o'clock, just waiting for me to drive her somewhere,
feed her and give her money. I have to give

(03:31):
her her allowance today I forgot and tell her where
she's allowed to be and what she's allowed to do
and what she's allowed to buy and go to her tournaments. Well,
she doesn't pay any attention to me, and I sit
in my own hotel where while she's hanging out with
her friends braiding each other's hair and just like wants
me to watch the game. But that's like my only purpose.
I'm just like a warm body. So it's something people

(03:51):
do not discuss enough. And dating at this age and
stage is interesting because dating at this age and stage
is kind of like purgatory. Also, you're just in purgatory
and you're trying. We're all saying to each other, like
you just don't know where you're going to be, So
you're trying to date but in your own community. But

(04:13):
you won't have a community because your kids want to go. Like,
I've met so many single moms in volleyball, and all
of them are kind of just operating for their kids.
But they're not really tied to the places where they are.
They're in these places because this is where their kids
are going to school. So you're dating, you're dating, it's

(04:33):
called dating and waiting. You're dating, but you're waiting not
for your final resting place, but for your final nesting place.
So I find it to be a very interesting phase.
So there are two dynamics I'm noticing in dating. I'm

(04:56):
noticing a desperation in women where there's certain women that
I know that'll be texting me, do you know this guy?
I have this guy, I went out with this guy?
You interested in this guy? They're almost wanting to horse trade.
They are like blood in the water. They want to
find someone who's a partner who's going to take care
of them, or they're just they know that they still
look good, they're working out, but like they've got a

(05:17):
bunch of kids, they've got a divorce, they don't have
like disposable income, and so now a guy can choose
them they're forty eight to fifty three, or a guy
can choose someone in their forties. But this forty year
old woman might still have young kids, and this fifty
something year old guy who can be nimble and is
almost on his way out. He doesn't want to hang
out with the forty year old with the young kids

(05:39):
because he doesn't have to, and he definitely could be
with the young girl, but she's gonna want to go
out and party in the nightclub and he's already done
all that, and or maybe he's not interested in that,
and he's running a business and he's going to board
meetings and he doesn't want to hang out or look
stupid like a fool to his ex wife and his
ex community with this young girl who's going in fringe

(06:00):
Swayed to Coachella. So now he could be with the
thirty year old springe suede Coachella to get the best
blowjob he's ever gotten. But then that girl is pretending
she doesn't want to have kids, but she is gonna
want to have kids, or he's gonna have to go
out and act cool and do molly with her thirty
something year old friends when he really doesn't want to,
or he does want to while he's experiencing his you know,

(06:23):
two old midlife just got divorced crisis where he's gonna
smoke pot and do molly and take edibles, but he's
gonna get tired of that real quick. That's a cliche.
Or he's gonna be with the one in her forties
who either wants to have another kid or has young kids,
and then he definitely doesn't fucking want that either, because
young kids are worse than being the old guy in

(06:43):
the club with the suede molly taking woman. So now
he's back to the fifty something year old divorced woman.
But she has her kids, and she's got more serious
bills and she's not as fun. So what she brings
to the table is that she can have a conversation.
She's been through it. She understands the music and the references,
and she's relating to the kids of going to college

(07:06):
or I've got a kid in high school, or we're
talking about where are we looking for colleges or looking
for apartments in the city to move them into. She
can relate to that. But she definitely has like the
three kids, and like the financial drag on his ticket
where he just got fucked over by his last wife
and still supports her. So how now he's got to
have another person on the payroll, you know, And frankly,

(07:29):
the thirty, forty, and fifty. For most women in this
country that want a guy who has money, they're going
to be on the payroll. So do you want the
thirty something swede Molly doing party or that's pretending she
doesn't want kids that really does. Do you want the
forty something who has young children that says they don't

(07:50):
want to have another kid, or probably does because they're
jealous of your ex wife and wants to knit it
all together because people are saying you got to get
him to have another kid, or they want the financial
security of getting him to have it other kid. He
wants no part of the fringe swede long term. He
wants no part of the young kids long term. He
also wants no part of the fifties. I have three kids,
and I'm gonna need you to support my dental bill

(08:13):
and support me in some way because I got fucked
over in my divorce and I really don't have that
much money and I need you for that. I have

(08:33):
had a lot of luck and opportunity with men at
all stages because at most of these stages, it's about
she who makes the goal, makes the rules. You gotta
listen to me. It's why you gotta fucking be working.
It's why pre wed doesn't work. It's why you gotta
be working, ladies. Because why Because starting in my mid

(08:55):
to late thirties, I had some money, not a lot,
but I had enough money that I did not need
to be on someone else's program. And in my forties,
I only had one kid, so I met men that
were extremely desirable, but they really liked that I was
nimble with one kid and have my own money. And

(09:17):
now in my fifties, it's fucking a gold rush for
me because I'm meeting men who want to talk to
someone who's business minded. I've still got the one kid,
so I'm light and bright. I can fucking pack that
suitcase and be anywhere I need to be at any time.
And I'm no blood in the water. I don't need
them for anything. I don't need them for a house.
I don't need them for money, I don't need them

(09:37):
for my teeth, I don't need them for business help.
I don't need any of them for anything. The rub
with me for these men is that they don't want
to date a man. They want to date the dough
eyed Bambi on some level with some people, but that's
also a dying breed because they've also been with the
gold digger, and they are so exhaling because we can

(09:59):
have a business conversation. I look decent in a bathing suit,
I could pay my own bills, and I'm light on
my feet. So the only drag on my ticket is
I can't be wherever somebody needs to be because I'm
still here until my daughter goes to college. So while
I think I'm fucking busted up and don't understand why
I'm an influencer, you know, getting the same deals as

(10:19):
thirty year olds, I also understand that because I've created
my own financial independence and value in business, that's going
a long way with men. Bliss, I'm funny, So whatever
you want to take from all of that, you take.
But women and men are both going through it okay.
And a lot of these men are emotional disasters. Women

(10:41):
get the bad rap for emotional disaster, and I'm just
telling you meeting a lot of disastrous blood in the water,
desperate women who want to find their next meal ticket.
It's giving desperate. It's giving a lot of plastic surgery,
a lot of that palm beach star wars bar look
a lot of extensions, a lot of nail, a lot
of working on the gym, and all of that worked

(11:03):
over stuff. I'm seeing a lot of that, all that contour,
all that beatdown from the YouTube makeup videos. I'm seeing
that in the Desperado women, because it's fucking rough out there,
and you've got to at least find your market. If
you're gonna look like a glazed turkey in a short,
tight dress, you better get your ass to Boca and
Palm Beach or you know, but wherever, like you need
to know your audience and where you're supposed to be.

(11:24):
Or if you're gonna be over plastic surgery, you need
to be in Palm Beach and Beverly Hills. That's not
gonna fly as much. It's gonna be a combo platter
in a place like Aspen. So you know, maybe you're
gonna do well in the Midwest where there are a
lot of wealthy guys but not a lot of those
glazed up turkey hot women that might land there, or
it might be like an alien. Just figure out where
the hell you're supposed to be and where it's not

(11:45):
too competitive. Is it Chicago, Is it Philadelphia? Where there
are a lot of wealthy men, but the talent is
not as competitive as a place like a Miami market
or Palm Beach or Boca. But then again, these men
are sick of looking at bimbos Miami, So figure out
where the hell you're going to be If you're going
to be a barracudah, that's going out there and looking,
and also your emotional well being, Like you got to

(12:07):
be a fully formed human being emotionally before you go
out there, because men are saying, God, is she a
fucking beating, she's a train wreck, et cetera. But here's
the good news and the bad news. The men are
fucking emotional train wrecks. And that's what no one talks
about because men hide there. Crazy women show it on
the first date, the second date. Okay, I've told you before,

(12:28):
you got to talk about what your attachment disorder is.
Are you anxious attachment? Are you disorganized attachment? Are you
attachment avoidant? You know what are you? And that can
seem crazy, but if you understand and could diagnose it,
that's it's necessary for two people to be in a
relationship communicating and understand how they communicate and does someone

(12:49):
get anxious if you're not texting back, and what does
that look like. But I've met a fair share of
men that are a mess. I've met the Catholic guilt
disaster mess that's basically paralyzed and can't function because they
don't know how to operate. I've met the anxious attachment

(13:10):
where the minute that something gets serious at all, they
want it so bad they're according it. They want it.
The minute it gets attached or communicative or anything, they
fucking they dissolve. They panic. I've met the guy who
suffers from anxiety. I've met the guy that suffers from
clinical depression. I've met there are a lot of these
men where it's in a different package. You see them,

(13:32):
they give strong businessman, but then when you get under
the hood, they're a fucking withering mess. And the man
that has to go to bed at eight o'clock and
is neurotic and doesn't like germs and doesn't like sharing,
and you know has you know is a mess about
over is a mess about being tired and travel and

(13:55):
so like, take your menu out and decide what you
can do and what you can't do. In deal breakers,
because you may be fine with someone that wants to
go to eight o'clock, or someone who gets super anxious,
or someone who's super needy. Maybe you were a nurse
in another life. You want to have a patient on
your hands and you don't mind it. You know the
character in White Lotus, the woman liked the woman with
the teeth that got made fun of on Saturday Night Live,

(14:17):
which we can unpack later. Her partner. She liked that
he needed her and she was saving him. I don't
want to save anyone. I'm not looking for the Jewish patient. Okay,
that's a reference to like English Patient, which was movie
years ago. But like, decide what you can deal with
and what you can't deal with. But by no means
are the women going to take over this fucking this

(14:38):
helm of being the disasters because men are disasters too.

(15:00):
He went to bat to the stern
Advertise With Us

Host

Bethenny Frankel

Bethenny Frankel

Popular Podcasts

Dateline NBC

Dateline NBC

Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

On Purpose with Jay Shetty

On Purpose with Jay Shetty

I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!

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

Connect

© 2025 iHeartMedia, Inc.