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May 24, 2025 43 mins

Kelly Bensimon’s twin brother Tommy is giving her the hard truth about her love life.

Did he think her first marriage would end in divorce? And Tommy gives his unfiltered opinion on Kelly’s “flirting” technique with Pascal.

Her twin is giving the tough love (and support) Kelly needs when finding her next partner.

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Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:12):
Welcome back to ID part two, which one of your
celebrity mentors, Kelly ben Simone. On this podcast. You've been
with me on the journey from talking about calling off
my engagement last year to manifesting my future husband to
going on set updates. It's been so much fun so
far and really really healing. I am so excited today

(00:33):
because I've mentioned this person several times in the show,
and I think having him on the podcast is going
to help you get to know me a little bit better.
So I am bringing in my twin brother. His name
is Tom caylorin, but he's known to me as Tommy.

(00:53):
Hi Tommy, Hi Kelly, Happy birthday, Having birthday Tommy, and
love you.

Speaker 2 (01:01):
You made it another year.

Speaker 1 (01:03):
Thank you for my president. You're the worst person to
buy presence for because you're like Jim Shorts. I'm like
Jim shortsone's Jim Shorts, asked.

Speaker 2 (01:10):
For Jim Shorts.

Speaker 3 (01:11):
But you know, forty again, Kelly, A baby.

Speaker 1 (01:19):
Again, Tommy. Let's get into this because we're on our
d part two and actually I've been I told you
about this, how much fun I've been having talking about
love and kind of you know, unpacking everything that happened
last year, but I want you to tell the listeners
what it was like growing up with us.

Speaker 2 (01:42):
Kelly, You're.

Speaker 3 (01:44):
You are one of the most unique people in the country.

Speaker 2 (01:48):
Like you, you whin the.

Speaker 3 (01:50):
You've topped the funnel at the top of people that
come down into the bottom of greatness.

Speaker 2 (01:56):
You know, you're one of those people.

Speaker 3 (01:57):
I mean you You've funneled your way to the top,
and you're just You've.

Speaker 2 (02:02):
Got all these unbelievable talents. You're so.

Speaker 3 (02:07):
Well spoken, and you're a hard worker, and you're a fighter,
and all those things are amazing.

Speaker 2 (02:15):
So, I mean, you have so much talent growing up.

Speaker 3 (02:18):
Well, I think all three of us are like that,
and I think it has a lot.

Speaker 2 (02:23):
To do with things that we had to do.

Speaker 3 (02:28):
You know, Dad was a lawyer, had a busy law practice,
but we still.

Speaker 2 (02:32):
All mowed the lawn every week. You know how to
operate a lawn more.

Speaker 3 (02:37):
I'm telling America, I'm telling the world on this whole podcast.
You can operate a push mower because mom and Dad
made you do it.

Speaker 2 (02:45):
And I just think it. I think it made you.

Speaker 3 (02:48):
I think it's made us all better people that we
mowed the lawn, that we you know. Did you know
when a when a car battery died, we didn't call
the gas station. We jumped the damn battery with jumper cables.

Speaker 1 (03:02):
Do you remember that, you me, Tracy, our older sister, Tracy,
the three of us we did. But I always got
I always when we when I move the lawn, you
got to be on the tractor, you were, Tracy, But
I always did the hand uh handheld because Mom wanted
to be perfect in the backyard.

Speaker 3 (03:21):
We actually never used we actually never used that tractor
because it was never worked.

Speaker 1 (03:25):
But Ray, remember.

Speaker 3 (03:29):
It was a mindset that they were workers, first generation
in college they had you know this is they didn't
there was nowhere to go back to ask for a
loan or to get money or to help out.

Speaker 2 (03:40):
It was them. Yeah, And so you know, it's just
thinking about you.

Speaker 3 (03:46):
You're just you just imby all those things that mom
and dad work so hard, and you just watched them
work and you just kept doing it.

Speaker 2 (03:55):
And I'm proud of you. I love you so much.
But you know, now we got to find you a mate.
Let's work on that.

Speaker 1 (04:04):
What was it like where before we get in found
me a mate? What was it like being my twins?

Speaker 2 (04:10):
I mean it was amazing.

Speaker 3 (04:14):
It was amazing because Kelly, you know when you when
we were growing up, you your your talent was just
so apparent, and your desire to be successful, it was
so apparent, and you know, it was just sort of breathtaking.
Your rise into the modeling world was sort of meteoric.

(04:37):
I mean when you know, mom and dad, so coming
from a family with a lawyer, Dad had enough money
to pay for you to get good pictures.

Speaker 1 (04:47):
Do you remember when you took my photos in the
backyard for Team magazine? Remember you took those photos.

Speaker 2 (04:53):
I don't remember doing you took a picture of meat
one time?

Speaker 1 (04:56):
I did.

Speaker 3 (04:56):
I took those professional photos, got into the the magazines,
and you got picked. And I remember being in the
audience at some of the contests and you would see
the other young ladies coming through and you were just,
you know, clearly the class of all those groups, and
you just would get picked and win contests and go
to the next and get a contract.

Speaker 1 (05:16):
You know what was interesting too, is like when people
talk about being twins, and you know, people ask me
about being a twin all the time, and you know,
it's like we were siblings. I mean, we are. Yes,
born in the same day, but we were siblings, and
you know, it was fascinating because like having you with me,
I was always I felt so confident, Like I was like,

(05:36):
Tommy's there, Tommy's there, Oh, Tommy's there, Oh, Tommy's right there.
Like I never felt like I was by myself or
I never felt like, you know, I have any reason
to be intimidated because you know, we were in a
lot of the same classes. We weren't in all the
same classes, but we were in, you know, in a
lot of the same classes. People ask me all the time,
they're like, do you guys have telepathy? Do you think

(05:58):
we have telepathy?

Speaker 2 (06:00):
It's just the stupid ast a question on the plan. No,
we don't have telepathy.

Speaker 3 (06:04):
I mean it's not No, this isn't We're not like
Siamese twins that were separated at birth, you know, and
share the same organs. Now we're born on the same day,
but we're brother and sister, Billy right exactly.

Speaker 1 (06:19):
And it's like, I mean, you know, they talk about
like nature and nurture, and we were you know, we
have the same nature and we were also nurtured in
the same environment. Yes, we can you know, fix anything,
clean anything. You ask us to do anything, we can
do anything.

Speaker 3 (06:34):
If your listeners are looking for that magic clean thing,
you know, it's have to debunk it right now, because
I mean, there are some things that have in common
with your sister Tracy that I do with you, or
you might. Tracy and I might be better at telepathy
as some things than you and I are.

Speaker 1 (06:50):
The two of you are lawyers. I'm not a lawyer.

Speaker 2 (06:53):
You're not shocker.

Speaker 1 (07:01):
Okay. When I get married to my ex, I'm happy
the best time, so happy to see you down. I
love you so much. When I got married to my
U now ex husband, what did you think about that?
Did you ever think we would get divorced? Be honest,
I mean we were too young.

Speaker 3 (07:17):
To really think about like that you would get divorced.
But I mean we were all worried. I mean I
think I was worried as just mom and dad and
Tracy and others were worried that, you know, there was
such an age gap between the two of you, and
that was just something that just worried. Is like, is
that going to Will that be successful? And you know,

(07:38):
will that continue to you know, go forward? And I
think I think the two of you had some good
years together, but I just you know, he he just
proved to be you know, I think there was some
I think he loved you.

Speaker 2 (07:53):
I think you loved him back, but it just proved
to be that he wasn't going to go all in.

Speaker 3 (08:00):
And and commit to being like uh that he was good.

Speaker 2 (08:07):
He would just lay down.

Speaker 3 (08:09):
In front of a moving train for you or walk
through a better broken glass for you. And I don't
know if I don't think it has anything to do
with you that you are great. I just think that
that's a little bit of who he is. You know,
it's been with many women before, and it's been with
many sins.

Speaker 1 (08:30):
I think too, it's hard. I mean it must be
hard for a lot of guys. I mean, obviously we
don't come from divorce, so that's something as well. But
I think it's really hard for a lot of men
to fill to fill shoes in a better way than
you and Dad, because you know, here I have this
amazing twin brother Tommy, and then I have my incredible father.

(08:51):
So I've been around such stellar humans that you know,
I don't like It's not that, you know, I want
a real relationship and you know, I've talked about this before,
like I would like a relationship where I I there's
my partner, there is my best friend, that we can
do all these things together. And I think that, uh,

(09:14):
you know, it's hard too because like I have such
high expectations because I was around great people.

Speaker 3 (09:21):
Yeah, but there are great people that you can be with,
you know, I mean, and we all are imperfect and
we make mistakes, so you know, I mean, and maybe
your next your second.

Speaker 2 (09:35):
Marriage that you had. I know, you've never got formally marriage.

Speaker 1 (09:37):
It's got last let's call it last second. Sounds like
there's gonna be a third.

Speaker 2 (09:41):
I don't know, but I mean you were with him
for a long.

Speaker 1 (09:44):
Time, like I don't know it's gonna be and.

Speaker 2 (09:48):
You were with him for ten or twelve years. I mean,
that was a very lasting relationship. But it was just
the most.

Speaker 1 (09:57):
Disappointing I guess too, Like because like you and your wife, Mimi,
you guys are so close and you're such a beautiful relationship,
and I like, and I've told Mimi this before many times,
I've said, like that's something that I want for myself
as well, Like I want that great relationship and you know,

(10:18):
it's like Mimi understands you, you know she and you
know maybe also really understands me, and so like that's
the thing too, is that again, It's like the expectations
are just like hard.

Speaker 2 (10:30):
I don't think you're right. I mean, I can be inconsiderate.

Speaker 1 (10:34):
Dumb Assmi's the best of the best.

Speaker 2 (10:37):
She's great. I love her. But I just wonder if
you have this story.

Speaker 3 (10:41):
Book view of how everyone's relationships are. I mean, she's amazing.
I wouldn't trade a minute of my life that I've heard,
my time with her ever for anything on the planet.

Speaker 2 (10:51):
But I mean not there.

Speaker 3 (10:53):
Are days when you know she would just like to
close the door and maybe never see me, or at
least not see me for another couple of minutes or days.
And so, I mean, relationships are imperfect and hard. It
requires work, and it requires kind of worst, you know,
saying you're sorry. It's so freaking hard. The whole that
you get gets harder to do. But that's the critical thing.

(11:15):
It's just like, can I just dump you to admit
that I was a dumbass and I was sorry? Yeah,
that's hard. So I don't know, I'm not sure I
agree with you. That there's this big storybook between the
two of us. I think there are many great marriages.

Speaker 1 (11:29):
I just see you guys as such a as just
like really, you know, it's like they always talk about
that missing piece, which I think is very beautiful. But
I don't thinking of it like that. I just think
that you guys are so beautifully compatible and I love that.
But you know what's interesting is that when I when
I was thinking about getting divorced, before I even got divorced,

(11:51):
and I, you know, spoke to mom about it and
she was like not happy, And you know, you and
Mimi were so supportive of my decision and not you
were supportive of divorce, but you were supportive of my happiness.
And I think that's something that's also very unusual too,
to have that kind of very strong family bond, because

(12:13):
most people like are jumping from their family, and all
I want to do is be with my family. So
I think that I think that, you know, at first,
I was so I was ashamed because I was the
first one to get married, and I was ashamed that
I couldn't continue with something that I had made a

(12:35):
commitment to. That's that's how I felt. But I never
felt that from you guys, because maybe you knew it
was happening.

Speaker 3 (12:43):
Oh no, I mean there's some things about him that
I really liked, and you know, I mean he was
very good to meet me, but I mean he was
also just you know, and if your beautiful daughters are
listening to this, this is not meant to be critical
of your dad. It's just like some of the things
that he wouldn't do for you from a career perspective,
and some of the things he did to you from

(13:04):
a personal perspective, or you.

Speaker 2 (13:05):
Know, just not okay, So anyway, we'll just leave it
like that. But mine, Yeah, anyway.

Speaker 3 (13:22):
But so then your your next path was into your
next relationship, which was you know, it's almost like you
you went, you went from the older guy to the younger.

Speaker 2 (13:36):
Guy, like you went the absolute opposite direction. Yeah, like
you could. You went as polar opposite as humanly possible.

Speaker 1 (13:54):
How do you think I navigated being a single mom?
I'm really genuinely curious, and you can criticis, but just gently.

Speaker 3 (14:07):
You were you know, you were a single mom when
you were married to Jill. I mean, let's be honest, right, yes, yeh,
So I mean these are basically your kids that you've
raised from birth by yourself.

Speaker 2 (14:17):
He was around some but not a lot.

Speaker 3 (14:20):
And I mean that's just an underappreciated thing that you
did and also trying to also.

Speaker 2 (14:29):
I think in the back of your mind you.

Speaker 3 (14:31):
Must have known that you may not work out with him,
and so you had to be prepared for the next
step of your life, and you navigated that being ready
for the next career step and then also raising the kids,
which was hard. You know.

Speaker 1 (14:44):
It's funny that you say that, because a lot of
people when they when they're like, oh my god, like
on Housewives, are like, oh my god, You've written seven bucks,
You've done all these magazine and all that stuff. And
I I respond to that by saying, if I had
been in a loving marriage, do you think I would
have had the time to write seven books and to
start two magazines and to do all these things and

(15:07):
to be modeling. If I was in a loving marriage,
I would be focused on my husband, uh, not just
you know, doing having this extra free time when my
kids were at camp or school whatever to do these
other things. And so I think too, you know, it's
it's been Honestly, it's been very hard. Not personally but

(15:31):
professionally to constantly tell people that, you know, I did
it for the right reasons. And I again, I also
had you and Dad there for the girls. So when
we would come for Thanksgiving, when we would come for Christmas.
I mean, you know, you're you're such a patriarch, and

(15:54):
Dad was such a is also such a beautiful patriarch.
That my girls, whether they did things that were really
really great or really really naughty, you know, I think
that like it was just it has been so nice
for them to you know, be around be around you
and that male. That male, the male in the in girls'

(16:15):
lives is such an important, important human because it really
shapes the narrative for them in the future of how
they're going to work and love. You know, if they're
you know, they choose to be with a male that
you know, help what that relationship looks like. And so
you know, I'm so happy, you know, I'm just so
happy that they had that they had you and Dad.

(16:37):
But what did you think about when I went on Housewives?
What were your thoughts, remember, gentle, gentle, you know, gentle, I.

Speaker 2 (16:46):
Thought it was amazing. You you know, you were great
on it.

Speaker 3 (16:50):
Your natural You're intelligenic and fun to be around, and
I think it's wonderful.

Speaker 2 (16:57):
I'm waiting.

Speaker 3 (16:59):
I'm just ready for the I'm waiting for the next
step in your career past Housewives.

Speaker 2 (17:03):
I think Housewives was the starting point for you, and
you got more in you.

Speaker 3 (17:09):
From that perspective, from whatever it is that video production
or video show or any type of the type of medium.
I think you're going to do something else. I think
that's not the that's not the apex of your career.
I think that's part of it, and there's going to
be more and you've got a real talent and it's
going to be great. So I loved it, and it

(17:29):
was a little bit weird at the start because when
Housewives was first on, it was very.

Speaker 2 (17:36):
New and very popular and very controversial.

Speaker 3 (17:41):
And I think one of the things why it got
so popular is because it caught people in those.

Speaker 2 (17:48):
Awkward circumstances and you got caught for sure.

Speaker 3 (17:51):
And now I just don't think it's just natural or
and you know, now they infew.

Speaker 2 (17:58):
You know, there's alcohol is just in fee use at
such a high level.

Speaker 3 (18:01):
I feel like, you know, purposely, I feel like but
I'm you know, I'm not there every day, so I
don't want to criticize.

Speaker 1 (18:07):
Too much, but I mean, do you think that do
you think they saw the real meme? Uh?

Speaker 2 (18:11):
Somewhat. Not no, not all the time, but somewhat.

Speaker 1 (18:15):
So it's funny that you say that because I sent
I have my og group chat and I sent a
photo because I'm always like, Happy Mother's Day, Happy Valentine's Day,
Happy Tuesday, Happy Monday. How are you guys? YadA YadA.
I saw this and I'm always responding to the group
chat and it's always crickets, except for when I sent

(18:37):
a photo of you. I said, it's my it's my
my twin and I have a birthday today, like have
no idea. They go, they go, I knew who's in
the group giants like me, Luan, Sonya, Ramona, Jill, Drenda,

(18:59):
and they go, they go, who said that? Luan goes,
who's that chills are? And that's her twin brother And
I can't remember what I think it was. Rona was
like she has a twin, I'm like ladies leads and
Luian goes, he's very tall, he's very handsome.

Speaker 2 (19:18):
That's part of the problem with the show is it's
not is not sickle. Oh good god, what.

Speaker 1 (19:26):
I called off my engagement last year? What were you
shocked or what were your thoughts?

Speaker 2 (19:32):
I mean not really.

Speaker 1 (19:33):
I just so like.

Speaker 3 (19:38):
His your relationship with him was I felt like there's
a lot of greatness in that, and there was.

Speaker 2 (19:43):
There was a lot of promise.

Speaker 3 (19:46):
Because I like being around him and and he shares,
you know, at some level, he shared a lot of
the values that I think you do and I do,
and Tracy and our family do, and so I was
kind of I was somewhat optimistic, but there was just
always a you know, a hesitance.

Speaker 2 (20:07):
He is you know, is he going to be able?
Is he going to be able to continue to you.

Speaker 3 (20:14):
Know, move forward with the relationship as an adult and
like as a responsible adult and not that he was
you know, adulteressts or drinking.

Speaker 2 (20:27):
This is not I don't want to give your listeners
that idea. That's not who he is.

Speaker 3 (20:31):
But you know, being a responsible adult is just doing
things you don't want to do, which is like going
to work every damn day and you know, producing for
your family and you know, making sure there's a place
for a roof over everyone's head that night. And I'm

(20:52):
not trying to say he didn't work, because he worked,
no question.

Speaker 1 (20:55):
You know what's interesting. People are like when they see
me on Instagram and I'm like, oh, I'm showing or
I'm here, I'm there, and they're like, you don't really
work like work? I work every day. But remember when
I was you know, when we talked about the prenup,
you know, you know you you were like, do you
remember what you said to me about the prenup? Not
really you said get it don't again?

Speaker 2 (21:20):
Yeah I probably did. Yeah, I mean I just why not?

Speaker 3 (21:24):
I mean, what, what's what's the hold up for you know,
having an agreement in a relationship when you're you know,
I'll just you know, spoiler alert post fifty for your.

Speaker 2 (21:37):
Listeners, it's shock her fifty.

Speaker 1 (21:42):
You're not supposed to say that.

Speaker 2 (21:45):
No spoiler alert if you.

Speaker 1 (21:47):
Just want to forty Tommy forty forty forty forty Yeah.

Speaker 2 (21:51):
Yeah.

Speaker 3 (21:52):
So anyway, like it sucks because he was you know,
he had a lot to offer, and I feel like,
you know, some of his family was you know, I
never met his mom. His mom sounded like a great
lady from what you from what you told me about her,
and was bored to meeting her, and you know, he
had a lot of he just has a lot of
things going, great things going for him. He's got beautiful kids,

(22:15):
and you know, he's going to figure it out for himself.
It's just, you know, I just think deep down inside
of it is just going to be hard for you were
just worried about, you know, just that day in and
day out grind of making your way through through life
was something I think you were a little bit worried about.
Not that there was anything imperfect about him, but like

(22:37):
was it going to keep going? You know, was there
going to be a sustainability to hit you know, his
professional development?

Speaker 2 (22:46):
And you know, I.

Speaker 1 (22:47):
Think too that's probably a lot of it too, is
from me and my insecurity and you know, constantly being
in the environment where I'm always reinventing myself. And that's
just been like a fear that I've had for so long,
is like constantly rein in renting myself and constantly being
the main provider. And that was big, that was a

(23:08):
big problem. What is the what do you what do
you think some of the patterns are it?

Speaker 2 (23:12):
I get what you're You're you're sort of talking around
in circles like.

Speaker 3 (23:15):
A circus ride. But I mean it is true. You're
basically saying, is how am I going to support myself?

Speaker 1 (23:25):
Yes? And without being yes, yes.

Speaker 2 (23:28):
It's really hard and so you.

Speaker 1 (23:31):
Know, continue not how am I? How am I going
to continue to do that?

Speaker 2 (23:35):
Right? Important?

Speaker 1 (23:37):
Yeah? So what kind of pattern to me? What tell me?
What are the patterns? What do you see in my patterns?
Is it my Is it that I'm super immature? You
can say yes, No, I really don't think so.

Speaker 3 (23:50):
I mean, I really like you've had some of your relationships.
I mean, but I just, you know, like picking your
second long term relationship that was just a disastrous choice,
and you that just played into yours, that played it

(24:10):
and sort of played into the what you always told
me about Jill's like I want to just be able
to I want to be with somebody that will take
me ice skating at Rockefeller PASA and do things like that.
So I felt like you thought that like marriage, and
you got married, you know, pretty young. Marriage should have
been a little bit more romantic in storybook, and you.

Speaker 2 (24:31):
Know, I think there are moments like that.

Speaker 3 (24:32):
But then I think you just were like, Okay, I'm
not married to Jilliemore, So I'm going to find the
storybook playing and you did.

Speaker 1 (24:39):
Anyway, move into the next thing, Tommy, what do you
think of What do you think of Pascal?

Speaker 3 (24:43):
I mean, I listened to a little bit of Pascal.
I think he sounded just like Jill, which was just yucky.

Speaker 2 (24:48):
So that just no good, he asked me.

Speaker 1 (24:51):
He goes, so, he's like, what would you do on
our first date? And I said, in like in jest,
and I said, I would take you to the my
Eiger Triangle to Gibson's to see my Playboy cover. And
he goes, what I said, I'm from rock Ford, Illinois,
and Gibson's is one of the most iconic restaurants in Chicago,

(25:12):
and I am so proud that they actually wanted my
Playboy cover. And I'm like, I would take you there
to show off the cover. And he was so wildly offended.

Speaker 2 (25:23):
Why would you say that?

Speaker 1 (25:24):
Though it's funny, because it's funny obviously doing that, but
that was so funny, and I wanted to see what
he would say.

Speaker 3 (25:33):
Sorry, Ummy, why would you say that?

Speaker 2 (25:37):
That's just off putting, That's bizarre. Don't say that. Okay,
here's listeners join in and call in text and.

Speaker 3 (25:49):
Again that's ridiculous, all right, keep going with your weirdness.

Speaker 1 (25:57):
So what kind of guy? So, anyway, to make a
long story longer, Pascal we ended up seeing I ended
up seeing meeting with him when we were in San
Francisco and Napa Valley and he was very, very very nice,
and so I said to him, I was like, what
kind of what kind of hair dresser would uice to see?
How do you know what kind of hairdresser? Juice do
you see yourself like? And he said, orbe like's the

(26:20):
most iconic characters in the world.

Speaker 2 (26:24):
You're losing me here.

Speaker 3 (26:25):
This is very sweet.

Speaker 1 (26:27):
It was very very sweet, very sweet, very very sweet,
very accomplished, very accomplished.

Speaker 2 (26:31):
That's awesome. But you ruined that one. Why did you
ruin that?

Speaker 1 (26:35):
What prescal thing about?

Speaker 2 (26:38):
Boy?

Speaker 1 (26:38):
Because I was having fun?

Speaker 2 (26:40):
That is dumb, though.

Speaker 3 (26:43):
People don't want to hear that about the viagrate triangle.

Speaker 2 (26:47):
That's just.

Speaker 1 (26:50):
I loved it.

Speaker 2 (26:52):
No, No, that is a disaster. That is going to be.

Speaker 1 (27:00):
Time is going to be like the group chat with
my date and be like, she didn't mean it like that.

Speaker 3 (27:05):
I just wish that the listeners could check chat in
right now to support me so that you could get
other realization of how bizarre that is.

Speaker 2 (27:24):
All right?

Speaker 1 (27:25):
What kind of guy do you think I tend to
attract or date? Is there like a type or is
there a personality trait that you think that I attract
or that I like?

Speaker 3 (27:37):
I don't think so, I mean, I don't There was
the one guy you dated from North Carolina for a
long time that was very successful, but he was noncommittal.
I think you're looking for to accomplished people. That's a
good word. I think you are. And all those people
that everybody you've dated, except for the one guy pretty
accomplished that just you know, the question was some of

(28:00):
is that going to be sustainable?

Speaker 2 (28:02):
Is that going to keep going? And so I think
you're looking for that. I think that's your trait.

Speaker 3 (28:09):
You had that one twelve year blip with the guy
with the white jeans and the flip flops.

Speaker 2 (28:17):
But other than that, what kind of guy?

Speaker 1 (28:20):
What kind of guys should they date?

Speaker 3 (28:21):
I think you should date someone who's honest with you
and themselves. You know what they want in their life
and what you want from your life, and and they're
honest about it, and you know that they know who
they are, and they understand who you are and that
you can coexist together understanding that you know, there are

(28:44):
things that are important to you, so those things have
to continue. You want to continue doing your lifestyle and
continue to improve and be better every day at what
you're doing.

Speaker 2 (28:57):
It's just who you are. You're not going to stop
doing that.

Speaker 3 (29:00):
Or whoever it is has to has to understand that,
and then you probably have to understand.

Speaker 2 (29:04):
It for them too. But I think you, I really
did think you would.

Speaker 3 (29:07):
I mean if you had the professional person and the
accomplished person, and you know, I don't want your listeners
to think that you're out looking for mister wealthy. And
it's not that I don't think it didn't work out
with your engagement because you were afraid that he wasn't
going to be.

Speaker 2 (29:25):
You know, mister Silicon Valley eye.

Speaker 3 (29:27):
But I mean, you're just looking for someone that's going
to have stability and professional growth and looking for growth
as a person as an individual, like and setting goals together,
someone that's honest, So like setting lifetime goals.

Speaker 2 (29:43):
I want to I want to be.

Speaker 3 (29:44):
Here with you in five or ten years, you know maybe,
and I talk about it this is this is kind
of where do we want to be in ten years?

Speaker 2 (29:52):
Where do I want to be with you? What do
we want to do? Where do we want to live?

Speaker 1 (29:56):
You know, it's interesting because like that's what I do
with seeing Teddy is I talk to them about like
what you know, in five years, what their plans are,
and like, you know, how I can help them. And
you know, we always talk together, but I've never had
that conversation with anyone. I've never asked anyone what they
were going to do or what, you know, what they

(30:18):
wanted to do. I mean with the girls, you know
sees like you know, mommy, now every now that I
had this great job and I'm feeling good about my
you know, financial success. You know, I once a year
I wanted, I want us to go on a great
trip with Teddy and you know, for us to do
these kind of things, and like, I mean it's just
I like, I've never heard that from anyone. So it's
also for me. It's just so amazing to you know,

(30:43):
think of my think of my daughters in that way.
But I also want them to you know, have their
own lives and to you know, be the best versions
of themselves. And I just want, you know, I want
to be there and watch every part of it. But
I've never never had that, never sent someone like, Okay,
in five years, we're going to go We're going to
be in flore you know, whatever it is, like Florida

(31:05):
or I know, Texas, wherever it is, Puerto Rico, wherever.
No one's ever ever had that conversation with me, well,
whoever asked me. I've ever even said, like what are
your thoughts? Like what do you what are the what
are your like lifetime goals or like even that any
of those kind of questions, I've never I've never even

(31:25):
kind of I never even thought of those.

Speaker 3 (31:27):
It should it should be a natural conversation that just
involves with the person and with your breakup. You know.
The unfortunate thing about him is that he's not his
and that might be part of the reason for that breakup.
Is like his kids are so much younger than your kids.
He has one child that's still in elementary school and
two other kids that are not even to college yet.

Speaker 2 (31:49):
So his life is completely unavailable.

Speaker 3 (31:54):
He can't well, I mean I felt like he was
available as much as he could, but I mean I
almost felt like when he was with me, with.

Speaker 2 (32:00):
Us, or like if he was at a holiday or whatever.

Speaker 3 (32:03):
It felt a little guilty to me that he wasn't
with his other kids, because I think his other kids
are amazing.

Speaker 2 (32:09):
They're great kids, you know.

Speaker 3 (32:11):
That was That's a loss for me, is those kids
not being able to see them because I just thought
they were impressive. And he's a good dad that way,
and love those kids. So but the problem coming back,
I'm doing my circle.

Speaker 2 (32:27):
Like you did.

Speaker 3 (32:27):
Is the point is maybe he wasn't ready to talk
about those long term goals because he couldn't see past
getting kids through high school.

Speaker 2 (32:36):
Really, so we need.

Speaker 3 (32:37):
To find somebody that's honest with themselves and honest with
you and you know, can see can see a future
like where we're going to go?

Speaker 2 (32:46):
What are we going to do?

Speaker 3 (32:47):
And it doesn't have to be like are we going
to move somewhere else, but like what do we want
to you know, do we want to take Like should
we plan a trip next year? Should we you know,
do we want to what do we want to do
for our holidays?

Speaker 2 (33:01):
You know?

Speaker 1 (33:01):
You know what's interesting is that like when I said
to him, you know, when we were talking, you know,
because I've never never been on a honeymoon, and so
I said, you know, because we're, you know, taking off
to get married. I said, why don't we take all
the kids to Disneyland for our for our basic for

(33:21):
our honeymoon. And he kind of looked at me. It's crazy.
But I wanted to do something for us, like all
of us. I didn't want to just do something that
was like him and I just going off and going
on a trip and coming back and being like, Okay,
I want to do something that would like really was
like family building. That's no, I know, but I've never

(33:42):
been on a honeymoon. I don't even know what honeymoon's life.

Speaker 3 (33:45):
Honeymoon is simple. You go away and kind of a
week with your new bride and then you come home
or a husband.

Speaker 1 (33:52):
I mean, what do you mean, Well, I never did that,
So I mean, if you don't remember, I got married
and then my ex husband went off and I don't
know if he went to like fashion Week or something.

Speaker 2 (34:04):
I don't remember that.

Speaker 1 (34:05):
But Kelly Tommy, do you think I should get married again? No?

Speaker 2 (34:08):
Wait, I forgot about that.

Speaker 3 (34:11):
I forgot about that about him going to fashion week,
And that is horrible.

Speaker 2 (34:17):
How do you not you know, have a honeymoon, even
if it's a couple of days.

Speaker 1 (34:23):
I never we went. I never went on hoymoon.

Speaker 2 (34:25):
Well, and that's just part of the reason why. That
was just you know, there was a lot of things
that were just not going to be successful there that,
you know, I.

Speaker 3 (34:34):
Mean, the fact that that was not a consideration for
him is hard.

Speaker 2 (34:39):
That's really hard.

Speaker 3 (34:40):
And that's just I'm getting emotional thinking about it.

Speaker 2 (34:43):
Kelly. I'm just so sorry. That is interesting a broken
part of your life.

Speaker 1 (34:48):
I mean, I honestly feel like and maybe this is
like maybe just like talking to you about this is
maybe like maybe having me come to a realization that
you know, like I I didn't have to you know,
you or my twin brother, I didn't have to take
care of you. You took care of yourself and we
did things together. But I always felt that I always,

(35:09):
like with Jille, I always had to take care of him.
I always had to organize everything. I had to like
you know, when he came back, I had to make
sure that like you know, he had like you know,
a place, a good place to live and a place
to do things, and you know, there was an environment
for him that he you know, he had friends, and
I was always taking care of him, and that obviously

(35:29):
taking care of my girls. And just some people are
nurtures and some people are I happened to be a nurturer.
I happened to love making sure that people are healthy
and happy and successful. It's just like part of.

Speaker 2 (35:42):
Who I am.

Speaker 1 (35:43):
But I realized because when I started this whole process,
I said to my producer, I was like, I'd love
to do this podcast, but I'm not going to do
it if I don't go through therapy. And so I started,
you know, I was doing I was going through therapy
and being on the podcast at the same time. And
one thing that I realized is that I don't want

(36:03):
to be in a relationship where I'm nurturing the other
person because that just puts me again. I'm off, I'm
always on my back foot. I'm always like how do
I how do I? How do I take care of things?
How do I organize things? How do I? And I
just don't want that in the next chapter of my life.
I want to I just want to feel like I'm
in a hug. I just want to like come home

(36:26):
and be like, oh, I don't want to be. You know,
it's like I've always been I'm gonna start crying, but
I've always felt so alone.

Speaker 2 (36:35):
And you're not alone, Keilly.

Speaker 3 (36:39):
I know you are people that love me, including me,
I know, kids in your kids.

Speaker 2 (36:45):
But.

Speaker 3 (36:47):
Thank you you're so let's go back to the answer
to the original question, which is should you get married again?
And you were kind of asking it in a funny way,
and absolutely, one hundred percent you should get married again. Now,
you're a therapist who is probably some New York crack
pot will probably say that's wrong, but I don't really care.

Speaker 1 (37:11):
No, she actually said you should get married for the
first time, is what she said.

Speaker 2 (37:15):
Okay, well, you.

Speaker 3 (37:16):
Know, I mean I'm a lawyer, so I don't know
about this stuff, but you know, but I mean, it
just seems like to me that having a mate is
really important, you know.

Speaker 2 (37:25):
And I was some we were having I was having
a conversation with me.

Speaker 3 (37:29):
About like there are people that have gotten that that
have been widowed or you know, and and or older,
and they're like, oh, I'm not gonna get why would
I get married again?

Speaker 2 (37:42):
You know, I don't want to get married again.

Speaker 3 (37:45):
It just I think to myself and maybe I'm a
dumb asset, but I'm like, why wouldn't you want to
get married again? Why do you not want to have
that person that cares for you every day that you
can count on that you've got that text from or
that call from or like it's what We're going to
do something together and it's going to be good.

Speaker 2 (38:04):
May not be quick all the time, but a lot
of times it's going to be good. So yes, you
should get married again. And I'm glad. I'm smart. Like
the therapist.

Speaker 1 (38:16):
Married for the first time she met, like have like
a real marriage, like a real She's like, that's what
you always wanted to the family, for your family. She's like,
go and get it. I'm like, Okay, I agree with her.

Speaker 3 (38:28):
Maybe she's not as crazy crock Pat crock Pat or
whatever a New Yorker as I said.

Speaker 2 (38:33):
Maybe she does some sense.

Speaker 1 (38:35):
So since I've been on the podcast, have you noticed anything?
I mean we have, I haven't gotten to see you
that much this year, But have you noticed anything different
about me?

Speaker 2 (38:47):
They're like, no, yes, is that the right answer? No?

Speaker 1 (38:55):
Do you think I'm more open? Do you think I'm funnier?
Maybe not?

Speaker 2 (39:01):
You know, I don't think there's been a big change.

Speaker 3 (39:03):
But I do feel like you, you know, you've you've
got to give yourself a chance to be with somebody that.

Speaker 2 (39:13):
You know, you got to give somebody a chance, and
they got to give you a chance.

Speaker 3 (39:17):
And and you know, it's really difficult.

Speaker 2 (39:21):
You know.

Speaker 3 (39:21):
The one thing that that Dips Pascal said on that
podcast I did agree with.

Speaker 2 (39:25):
I kind of liked it.

Speaker 1 (39:27):
What did he say?

Speaker 3 (39:28):
He said that, you know, if you're going to go
out with people, you shouldn't always expect that this you're
going to go out.

Speaker 2 (39:33):
On a date and meet your future mate.

Speaker 3 (39:36):
You should go into it with the expectation that maybe
I'm going to meet somebody or make a friend, which
you know, secretly, I think if you're going on on
a date, you kind of have that hope right that
I'm going to meet the person that I'm going to
you know, hopefully this will turn into romantic.

Speaker 2 (39:51):
Yeah. But I guess really.

Speaker 3 (39:53):
For I guess what he maybe what he's really trying
to say is, look, don't put so much pressure on
it when you go out with somebody, you know, don't
give them the a whole bunch of questions. Just find
out about them, and you know, let them find out
a little bit about you, and you know, just kind
of be honest because at this point in your life,
just you know, I think honesty's the best policy to say. Look,

(40:15):
I mean, I'm after a future. You know, you seem great.
Can we do this together? What are you after? And
if the guy is just like a social climber or
somebody that just wants to, you know, get his picture
taken with you, then you know you'll figure that out
pretty quickly.

Speaker 1 (40:30):
It's interesting because one of my friends on the podcast's
her name is Cheryl Burke and she's on Dancing with
the Stars and she is such an amazing human. I
love her so much. And she said that she's like
Cheryl Brooke, Cheryl Brooke from Dancing. Sorry, she's amazing. I
love her.

Speaker 2 (40:42):
She celebates an incredible dancer. Should watch her all the time. Lohh,
my god.

Speaker 1 (40:48):
She's so cool and we've become really good friends. And
she said to me, she was like, I she goes,
you need to ask more questions, and she goes, not,
she goes, some people are like you have to ask,
like how many kids? Like all these things. She's like, no, no, no,
she goes, you're not answering asking the right questions. She goes,
if a guy is divorced, you can ask, Okay, why

(41:09):
are you divorced? But she goes, don't go into it.
She goes, the way he tells you, you know why
he's got divorced. So it's like whether there was infidelity,
if there's no sex or whatever it was. So I
really really love that my friend Deanna, we've become really
really good friends after spending a lot of time together.
And she was telling me how she doesn't know that

(41:30):
if she would ever get married, you know again, and
if she did, she did from having a prenap, which
is all these things are great. But she was really
good too with me and saying that, like and she's
done a lot of work on herself, and she just
said that like that I'm not asking the right questions
and that I need to listen what they're saying and
move on. And you know, you just said that, you
said the same thing. You said, like you need to

(41:51):
find out like what their goals are, like what do
you want to sail for the rest of your life
or you know, to the sunset? Like are you, you know,
in a ten year plan of work? Like what did it?

Speaker 3 (42:01):
Is it? So?

Speaker 2 (42:02):
I agree with Deanna, you need a prenup. You need this,
you need that.

Speaker 3 (42:06):
Maybe you to need a prenup right with that particular
last relationship you need?

Speaker 1 (42:12):
Yes, but agreed, agreed. I wouldn't. I don't know if
I would. There's there would be. There are certain situations
where I probably might. I wouldn't get a prenup.

Speaker 3 (42:19):
I mean you might go in and figure out that
maybe you don't need it, and right, you know, anyway,
I just don't.

Speaker 2 (42:26):
I don't think you should go. I'm not getting married again.
I'm going to get a prenup. I'm doing this, I'm
doing that. Maybe I don't know.

Speaker 1 (42:32):
No, no, no, no no, I'm open to it.

Speaker 2 (42:34):
All.

Speaker 1 (42:35):
I know that I know my person is out there.
I love you, Tommy. Do you have any parting advice
Tommy to give to my listeners on I Tube perdue.
They are gonna love you, They're going to eat you up.

Speaker 2 (42:47):
What's notts of love advice? You get out there and
find it, listeners. It's out there for you.

Speaker 3 (42:55):
There are great people all over this country waiting to meet.

Speaker 2 (42:58):
You, So go find them and be happy. I love you, Kelly, so.

Speaker 1 (43:01):
Love you Tommy, Happy birthday, Happy Birthday. This has been
so much fun. Thank you Tommy for coming on the podcast.
Are you single after a divorce and needing some guidance?
I am here to help. Email us or call us.
We're here to help. All the infos in the show notes,
follow us on socials, and make sure to rate and

(43:23):
review the podcast I Do Part two and iHeartRadio podcast.
We're Falling in Love is the main objective.
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Host

Jana Kramer

Jana Kramer

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