No Prenup, No Wedding with Kelly Bensimon
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Then this show ain't for you. Welcome to I Do Part 2, where your hosts today have said, I do eight times between the three of us. Eight times! How was that for an intro, Jana Kramer? Listen, TJ, I feel very targeted in that. You're not, no, no, no. You should just feel seen, Jana. Thank you, finally. Because on this end down here with TJ Holmes, hello, and Amy Robach, hello.

four I do's down here as well and a fifth in the making we should argue on this possibly possibly so yes I'm not targeting no rush right I'm not targeting but welcome everybody so Jana we have to say it is so good to have you in studio Jana is here with us in New York

I love New York. You guys, this is such a fun city. It's so great. And to hear with the beautiful Kelly, I mean, this is awesome. Yes, we have what we should mention. We have the amazing Kelly Ben Simone, right? Did I say your name correctly? All right. Kelly Ben Simone is in the house here. And she is going to be, we mentioned this in the first episode, one of our celebrity mentors. Are you prepared to mentor us, Kelly? I am.

I hope so. I'm working on it. One day at a time. Kelly, are people coming to you for relationship advice more so now than they used to? I mean, in the past month and a half, I've become like the relationship guru. Wow. Everybody's asking me for advice.

which has been really, really sweet, but it's also like bittersweet because I'm just like, I hope I say the right thing. Well, you always say the right thing in the right moment because it's authentic. And I think at some point we were talking about that. Authenticity is a big part of reality TV and sometimes...

It's not, but you've always been the one who speaks her mind. Always. And for those who need an introduction, I don't think many people do, but you obviously hopefully remember Kelly from The Real Housewives of New York and Ultimate Girls Trip, and recently making headlines for ending a wedding to be four days before the nuptials were set to actually take place, all because...

Your fiance wouldn't sign a prenup. Is that the only reason why the wedding was called off? I thought the only reason, Amy. I didn't think so. How long were you guys actually together? Because the first thing that I read, well, I thought, wow, that's so powerful and that's more power to her. But then I was also like, that makes me sad for her because how long was the relationship? That must have been really hard to part from that. Yeah.

Yeah, I mean, we were together for over a year and a half. And everyone's like, you're a runaway bride. I actually ran to myself. It was a very crowded, messy environment on his part with ex-wives and all these kids. And I love children, but it was just very, very, very messy. And I just couldn't handle all of that.

I'm very neat. I raised my girls on my own. I provided for them, educated them. I'm like the mama bear of all mama bears. And to see all this chaos all the time was just not for me, coupled with the fact that

That, you know, I'm the daughter of a lawyer and if I'm going to get married again. I mean, I've been single for so long. Not because I'm like single. Like, you know, someone would like, they're like, well, you're single. I'm like, well, I'm not like single, like out there. Like, oh my God, I'm single. I'm single. Introduce me. Introduce me. I'm just not married. You know? There's the difference. There is a total difference. And you're divorced. Your first divorce, your only divorce, correct? Yes. Was back in 2007? Yes. So you have been single. With a mediator. With a mediator.

you know, it was like, it was, and was there a prenup obviously in place then? No, there wasn't. Um, but it was like a mediator, but it was also different. I was young and you know, he, I was young and made, starting to make money. He was, you know, older and starting to make money. And so we were like, we were really building, you know, I helped him build, um, his career and it was just a different environment. It was a different time too. Um,

You know, in 2007, people weren't like, get a prenup, take care of yourself. You know, women weren't like, oh, I need to watch out for my finances. You know, it was a different time. I mean, people didn't even talk about, really, about marriage. I remember going on, when I was first on Housewives, and, you know, I was like, I'm a single parent, and they were like,

So that's, we got one of those in the room. Yeah. It was kind of like I had like leprosy or something, you know, I was like, I'm just single. Like I just raised my kids on my own and I was, you know, also young when I got married. Um, but just, it was just a different time. Now it's like people are like, I'm single, I'm loving life. And back then, um, it wasn't really perceived that way. So I asked kind of an insensitive question. You can, I think, uh,

Push through it. You'll make it down. Just get through it. Because I don't want to sound... I don't want to put him in a bad light, but does he not have a lot of money? I don't... I mean, I don't really know what his money situation is, which is also a bad thing. You should kind of know what the finances are, the family finances. I just knew that...

I have two children. I've worked really, really hard. I have a lot of earning potential and I want to make sure that my girls are protected for the rest of their lives. I mean, that's why I'm making money. I'm not making money so I can go to Tom Ford, although I do love Tom Ford. And

And was his stance like... I'm just saying, you know what I mean? We're in New York. People are like, oh my God, they're just spending money like crazy. Well, that's not really how it is. Like, I just want to make sure that my girls are obviously educated and have a good, you know, framework. But I just want to, like, ensure that they can do whatever they want. And he didn't want to sign it because he... What was his reasoning for not signing? He just said no. Just flat out no. Yeah. He was like, we're not doing this. I'm like, we're doing what?

So we're going to combine everything? I'm like, wait, no, no, no. We're not combining anything. That's not happening. Okay. I know, Kelly, a lot of the headlines like that to write about that didn't get married or marriage off because of a prenup. But...

Clearly, there was a lot more going on than the prenup. That might have been the straw that broke the camel's back. Yes. But you all... It's fair to say now you all shouldn't have gotten married. No. And I touched on that. I just was saying, with the messiness and being crowded, it was just too much. It was just, you know, I have two girls and I have a big life. And, you know, just with all of the messiness, it was just too much. It was just a lot. And, like, some people have the bandwidth for that, but, like...

you know, I travel, I work in five states. I'm traveling a lot. I'm all these, you know, different shows and trying to just to have a good time with my life. Now that my girls are, you know, educated and have jobs and are feeling good about themselves. Like, I feel like I'm like, oh my God, I'm like,

you know, 18 again, like world's my oyster. Like, let's go for it. What can I do now? Like where before I was more like whatever was making money with the things that I would just be laser focused on. And now I'm just very excited about, you know, new opportunities. And I think that's something, you know, that we're not seeing that much of, you know, with women in their fifties. Yep. You know, I hear you. What are y'all's thoughts on prenups?

You know, I think before, it's nice to be in a position where you need one. You know, I too got married young the first time at 23, and even when I got married again in my mid-30s, there wasn't a lot to speak of. So it wasn't even a consideration. But once you... I am too a woman in her 50s with two daughters who rely on me solely for their financial support. I've never considered a prenup before, and I don't know how I feel about it now. I know that I have created a trust,

after having learned some lessons during one of my divorces. And so I've taken that action. And that has left me feeling more protected for my daughters. And, you know, everyone's got different avenues, but I learned the hard way that you do need to keep that in mind because as the saying goes, you don't know who someone is.

until you divorce them. So I'm not a lawyer. I'm not trying to, you know, tell people about the law, but I'm just, you know, explaining what I know. And, you know, it's either you either have a trust or a prenup.

So, you know, if you're going to go into a relationship and you want to say to the person, okay, you know, we're going to get married. I mean, at the end of the day, like it's a transaction. It's always been a transaction. Like it's not some new thing. People are like, no, no, it's for love. Yes, it is. But when you're sharing finances, whether it's $1 or $10, that's your money that you made. And the person that you're with should be excited about that and be saying like, that's a great, I mean, if he had said that's a really good idea,

I really appreciate you taking care of yourself and putting your family first. I probably would have married him even though everything was messy and even though there was just so much... It was so crowded. I probably would have been like, you know what? I really appreciate that but because...

because of that really rubbed me the wrong way. I was just going to say that's about I think so much of I can only speak for women we want to be supported and sometimes that's getting the support to know that we can support ourselves and if that's not celebrated by the partner or the person who you want to spend the rest of your life with that is a red flag. Well and yeah and I will say this too a lot of and I don't know if this is just now but

At least five girls that I've spoken to about prenups, it was the guy that didn't want to sign the prenup. It was always the guy having the issue with it. Like, why do you want me to sign that? And, you know, my girlfriend who was, you know, she's...

she was my last text. She was just like, I, he won't sign it. And it's frustrating me that he's just like, I've built this business. I've done this. And there's, and I have multiple examples of, it's always the guy rubbing up against it. So I'm curious, TJ to direct it towards you. Like, what do you think that is with the man to not, I was about to ask you, is there an imbalance in all those friends? Was there some kind of financial imbalance or just, I think maybe some are a few are, um, equal in pay. And then the others, the women do have more money.

why did you ever, and I'm going to ask. TJ, I'm going to you first. Don't you dare try and put this back on me. I promise I'm going to answer. I promise. I'm sweating over here in my wool little bag. Did you ever do one? Did you ever use a prenup? I asked you first. Okay, that's fine. I never have. It's my answer, but then I have an opinion on them as well. Okay. But have you ever used them? If she came to you before you guys get married and she says, I want a prenup, would you sign it? I'll sign whatever she wants me to sign if it means I can marry her. Oh,

I completely pulled that out of my ass. I didn't know. But it was just documented. No, but my feeling on it, and this might sound crazy to you all, Kelly Jenner, is that

There's something that's so unromantic about it. It's something that does make it feel like a business transaction. I get it. I 100% get it. But it just feels icky to me. So I have always been on the higher end or the one who makes more money in my relationships and marriages, but it never crossed my mind to do so. So then you can do a trust. So that's what Amy is saying. So you either do the trust, and if you don't have a trust in place, then you should do a prenup.

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In my last marriage to my husband of almost seven years, I did not have him sign a prenup. To me, it was like, we are getting, this is my one forever and we're getting married. And...

When he cheated the first round of affairs, when he was in rehab, I made him sign a postnup. But that did not hold up in court. It was not going to hold up in court. My lawyer had said when I finally divorced him that postnups don't hold up as well as prenups. And that he... And he told me he was going to fight the postnup. And so that's when I just went into my own brain of Excel, Google Sheets of, okay, what I think is fair and what is, you know, without trying to take. Because it was...

I earned most of the money in that relationship. Um, so now in this new relationship, it was, it was a really hard conversation to have because I have my entire team of people and lawyers and business managers and looking out for me. And my lawyer was like, this is like getting health insurance. And I'm like, I get that piece of it. I was like, but I'm like, I'm struggling with that. He's like, well, why wouldn't you have health

insurance for your life. This is the same thing. I'm like, but it's not. I'm like, he's the love of my life and I don't want to have a prenup. I don't, I go, having said that, then I look at the other side. I realized how much I lost almost half of my money in my last divorce and

that I worked really hard for. And I come from that single mom of their heart. My mom was a single mom. This is not for me. None of that money is for me. It's for my children. And so if I just want to protect that, and I think when I had the conversation with my husband now, you know, he was very much like, Liu, it's not what we're already going into this to not be together. Like it doesn't feel romantic. It's like, and I'm like, I know. And I was like, I don't want it either. Like zero part of me wants it. And he's like, I will sign it if you want me to sign it. And,

you know, I'm not going to actually say what the end decision was, but for, for me, it was a, it was just a really tough conversation to have. But isn't that so nice? Sorry. It's all right. It's not so nice though, that he said like, if you want that, like that, at the end of the day, I think I needed that piece. And then whatever we ended up doing was the right. And I think that that was the other thing too, is that,

There was no gentle conversation about it. There was no, like, you know, I want you to be happy and healthy and make sure that you're safe. And I think that's one thing that is... You know, there's so many roles being reversed. There's a lot of women that are making a lot of money. And...

you know, it's like when I, when I was dating before I met him, you know, a lot of guys would be like, Oh, you know, Kelly's going to take care of this. And Kelly's doing this and Kelly's doing that. I'm like, why is Kelly doing everything? Like, hello, you can like, you know, start doing things as well. And, um,

You know, I just, I just feel like there's nothing wrong with making money and there's nothing wrong with being, you know, supporting your family and putting your children first and like wanting a nice life for yourself. There's nothing wrong with that. And there's nothing wrong with wanting to have a partner, uh,

that's involved in that as well who's like hey you know what you're doing such a great job and I'm so proud of you I still don't get why he would just he just said a blanket no he didn't just give an answer like a response you say he just said no and moved on I mean what was the logic behind it am I missing no I was going to ask that question if you didn't the same exact question he had to give you some reason why besides just no I refuse

Well, actually, he said to me, no. And then he was like, I'm going to have my lawyer go back. And I'm just like, no. That's where it's so trans-art. That's where it gets so icky. And I was like, no, no, no. We're not doing this back and forth. It's like, this is it if you want to be involved or not. And...

That's it. That was it. And he had it for a long time. It's not like he had it like a day. Well, I mean, I know this is crazy, but my brain goes straight to a place where, you know what, it all happened the way it was supposed to because if he went to that place immediately with you asking for a prenup before you're even a married couple...

My mind goes to what that divorce would have been like had it not worked out. Well, like you said... There's no conversation. It's like, I'll take it to my lawyers. That's the worst possible response when you haven't even gotten married yet. Well, just like by... I mean, so we're talking about like, you know, would have, could have, should have, like all these different things. But here's the good news. The good news is the law doesn't care if you're madly in love or if you hate each other. The law says...

you get a certain amount of money regardless if you don't have a trust or a prenup in place. So, you know, you can be loved as much as you want and then when something happens, good, bad, or ugly, and all of a sudden, like, all that money you've worked for on...

the male part or the female part is going to that other person. Like, just like you said, like you had to give money to another person who's like cheating on you. I mean, how does that make you feel? You don't like sleep at night and be like, Oh my God, I'm so warm and fuzzy because he cheated on me. I gave him so much money. It's more so just, and that is the only, that is the only piece that like causes still friction with me and my ex is because I pay him child support. I have the kids 70% of the time. He took almost half of this money. So it's like, it's frustrating to have that,

Where I'm like, I worked my ass off. I came from nothing. Like, my mom worked three jobs. I'm the girl that only saw negative in her bank account. So now I'm to a fault, too much of a hoarder in my bank account now because I'm afraid of not being there, not being able to support my kids and their sports. Like, I had to quit figure skating because my mom couldn't afford it. I never want to have to tell my kids, you can't do a sport because mommy doesn't have the money. So like...

I want to like make sure they're protected. And so, you know, like you said, when you divorce someone, like he even said, I won't take your money. Well, no, because when the divorce is...

They're going to go after it all. The law doesn't care. I just got chills. You know that. You're getting divorced for a reason. You ain't friends anymore. You're not in love anymore. No. They're going to come after you. When everyone starts lawyering up, it goes from amicable divorce to very much the opposite very quickly. And I think that's part of the point of this podcast, which is pretty cool because...

Yeah.

I mean, with my first ex-husband, my only ex-husband, you know, we had a mediator and, you know, it was my, you know, our accountant and the mediator and we went through everything and I just made sure that my ex-husband was safe and that I was safe. And, you know, it's like,

I come from like good stock. I'm like, I want people to feel good. Like I want them when they're around me to feel good. I want them to like feel to trust me. That's like super important for me. And my ex-husband, you know, I mean, I made sure that he, that we were both like in a good place. And, um,

That was really important to me. And so to come into a situation where I wasn't feeling good after I'm the one that like tied the bow on for my first husband, you know, my, my only husband. Well, you're just getting caught up in all of our lives. First husband, second husband, eight husbands. Did you consult with anyone?

With your decision to call the wedding? With my lawyer. Yeah, with my lawyer. No friends or any? And I also, we had just gone to Jamaica with my girls and we were having, and my girls were not happy. My oldest was not happy. My youngest was not happy. And I'm just like, what am I doing? My kids are, my kids that are like my everything are not happy. And I've broken up with guys before that I've been dating that I was like, oh, they're fun. And my kids were like, we hate him. I'm like, okay, you're fine. Goodbye. You're done.

So like they've always been my priority and they just weren't feeling good too. They just weren't feeling it. There was a lot of, where does that love go then? Cause obviously you love this man, you know, like is there any regrets? Do you like, where, where do you place this love? Or was it just an immediate turnoff that it was a turnoff, but it was also just like, I just, well, I mean, if you remember too, it was like I had to move out. And the first night I'm in my ex, my daughter was staying in my ex husband's apartment and

And so I like no place to go. So I'm like, okay, I'm going to go with my daughter into my ex-husband's apartment. And there are all these like sunny angels. And then he's got these like symbols. And I wake up and I'm like, what is going on with my life? Do you know what sunny angels are? They're these like very like little crazy figurines that kids love. They're like kind of...

oddly pornographic. But for kids, they're weird. I don't know. They're not mine. But anyway, I was just like, this is not my life. Like the Sunny Angels and this art and I'm in the bed with her and the dogs and I'm just like... In your ex-husband's apartment. I'm just like, I'm going to lose my mind. You got to that place, Kelly, but how much courage did it take? I'm just curious, for you to actually say, I'm calling off the wedding. What was that conversation like and

Obviously, you knew this would be everywhere because it's been such a public relationship. What went into the decision? How much courage did it take? And how did it go down?

So I was getting a colonic. A colonic. Those are great. I used to have those in Los Angeles. Haven't had one in a while. God, they're so good. Worst feeling in the world, though, right? When it's about to come out. Is this where I step out? This is where I... Oh, this is the time where I step out. This is... Oh, colonics are amazing. So literally... Have you used a catamaran before? I don't even know what you're talking about. Amy, they're just like... They're just amazing. Anyone who has not gotten a colonic, I love them. Oh, wow.

Makes you feel so just like light and energy. Yeah, I was feeling very stressed out. And so I got a colonic and I'm laying down and I was on my phone when I was getting a colonic. And he said something to me along the lines of, you know, you need to if you're going to cancel the wedding, you have to do it now because there's a cancellation policy. Oh, my God. He didn't say if you're going to cancel when he's like there's a cancellation policy for things.

And I was like, I'm sorry, what? I'm sorry. Did I hear that? Did you just text me? I didn't hear it. I was reading it. I'm like, did I just, do I need my readers on? Did I just see a cancellation policy? That's hurtful. And I just was like, we're done.

It happened over text where it was? I saw him, yeah. And I called him and I was like, what did you just do? First of all, are you talking to people on my behalf? Like, are you talking to people that I know? Because that's not okay. Because if anyone's going to break news, I'm going to break my own news. And listen, you know what?

He's a really genuinely very nice guy. He's just not my lobster. He's not my lobster. And I want someone that makes me feel good about myself. I want someone that pushes me to be the best version of me. I don't want a messy environment. I don't want someone talking about cancellation policies. I want people to be like,

I love you so much. Let's fight for this. I'll sign that piece of paper. You are the best. Let's not do this. It's the rom-com ending that we all want. When they come back and they fight for you. It's hard. You almost break up, but they come for you. We want to be able to write

are we canceling this or not? And then having you guys say, no, I love you so much. I want to do this. Yeah, I want to be raiding outside. We'll always be the high school girls. If he had said, you know what? Money doesn't matter. I just want to be with you no matter what. Let's figure this out. You would have been all in. No, like cancellation policy. I was like, I'm sorry, what? Yeah, we want to be chased. Yes, yes. Chase me, chase me. Okay, you were together two years in total, right? Okay, you just said something. How long in that two years, if you look back?

When did you actually know he was not your crustacean? He was not your lobster? When did you know in those two years? I knew like a couple of months in there was an issue. A couple of months? Yeah, and I was just like, what is going on? Who are these people? Like, what is happening? See, doesn't that happen? You knew that long ago, but it took two years to finally flesh that out. Is that always or often the case? I don't want to say just with women.

But with all of us, isn't that a problem? Oftentimes we ignore the signs that you clearly saw early on. Yeah, we do. I think, yeah, because we want to push through and go, okay, maybe this will change or, you know, we want the love or he's good enough maybe, but it's not the best.

And you know what? That's really interesting that you said that, Janet. You know, he's like not good enough. And I feel like people are like, after I got, you know, I called it off. I was at this restaurant in the Hamptons. And I sat with some people that I really respect. And, you know, he said to me, you know, well, Kelly, everybody has luggage. And I was like, okay, Louis Vuitton, fine. But like a storage unit? Like, no. I just can't.

I don't care how this lands, you guys. I don't care if you guys don't understand. No, but don't you think older in life, though, we have more stuff to put into storage? Like, we've got, now it needs to be. So I have really nice furniture, so I don't have room for everything else. But it's how you organize that furniture. It can't be all untouched. The container store is amazing. All these little plastic things, you can put them in.

It has to be labeled and nicely put away, which is healed and worked on. It can't be like hoarders. Yes. No. When you walk in and there's just mess everywhere. Just like falls out. Agreed. So the advice for someone finding love that feels that initial, I knew within the first two months, what was that piece that would be the...

the advice that you would give them so that we can stop people in their tracks to then meet the right person? Understanding your bandwidth, I think, is like mandatory. So for your own self, you have to, instead of people saying like, this is okay, this is not okay, you have to understand your own bandwidth. For some people, what's messy...

is not that messy. For other people, what's a storage unit is just like carry-on luggage. So you just have to understand your own bandwidth and be okay with that. Do you know what I mean? And you guys have been through a lot together, but you're so connected. Just been talking with you before we even started this. You guys are so...

And just so just connected, like, you know, it's you were like, look at each other when you were talking, you know, it's not just like, oh, my God, what are they going to say? I mean, you know what she's going to say and you know what he's going to say. And it's just beautiful. And just being able to be open to that other person.

And so I don't think the person, you know, it's like everyone's like, they're like, oh, I want to, you know, Jill Zarin used to say, I want a PJ. No, no, no. Everyone go for a TJ. Like that's like, that's the real, you know, that's just what life is about. Just like sharing memories. So you have to understand your bandwidth and know like what you can handle and kind of what you can't.

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We both have great taste.

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We'll say first, thank you for the kind words. No, it's true. I was like, oh. Spent a short time with you before we came in here. But was there ever, did you all spend any time trying to reconcile after you cut off the wedding? Was there ever a chance? Did he say, hey, I want to go to therapy maybe? Yeah. Oh, we did go to therapy once. And I was like, this is not therapy. I was like, this is babysitting for him. I was like, I'm not doing this. This is like, I'm like, the therapist is supposed to be like, here are the tools in your tool belt. Use this one. And she was like, oh, you're so handsome and cute and friendly.

fun and everybody's not nice to you. I was like, I'm going to kill myself. He charmed the therapist? Yeah, he's a charming guy. He's a very charming guy. He's a great guy, just not for me. He's just not my lobster. Well, this show is a dating show, so now we know that you're out there in the dating world. Oh, wow. He's lit up. Oh, yes. Is he outside? I don't know. I don't know.

Wait, did I hear a rumor that you were dated with Bethany's? Oh my God. Oh boy. This is like crazy. So my last Bethany's ex, the one that no, no, no. Okay. So I'm in the Hamptons with my, cause I'm like, you know what? I'm going to rent this house in the Hamptons. I am getting my license in Texas. I,

It's 180 hours. I'm going to study, do my stuff, spend time with my kids, learn to play polo, learn to do something that's like so difficult. I'm going to learn that and just really, you know, take myself out of like all my little, you know, drama filled, you know, environment and just go do something that's different and just like get excited about life again.

And so, you know, my daughter's like, mom, you know, she's like, you can just go on Raya. But you, you know, at the beginning when I was on Raya, I was like, people are like, they're like, oh, just say hi to people. So I was like, hi, hi. I was like, this is not working for me. It always just ends at the high. Like, I think people just want to be like, all right, you're cute, cute. We like each other. And then it just, the conversation ends. Right. When I was, yeah, before when I was saying, I was like, hi, hi. I was like, this is not happening. Yeah.

And so she's like, mom, she's like, she's like, say something like your trouble. And I was like, oh, hold on.

So I was like, you know, I usually say aloha. That's usually my thing. I'm like, aloha. And they're like, are you from Hawaii? I'm like, I could be like, I'm, you know, I love traveling there. Exactly. Thank you, Amy. So I was like, okay, I'm just, you know, like, and then my other friend is like, she's a lawyer. She's like, it's a numbers game, just like all these guys. So I'm like, okay, like, like, like, like, oh, okay. Like, oh, oh, yeah. Like, like, like, like, whatever.

And then they, you know, I'm like, aloha, aloha, just trying to be polite. And my oldest daughter's like, you're not supposed to do the first one. I was like, it's aloha. It's not like I'm saying, like, let's have sex. Like, and she's like, ew, you're so gross.

So, cut to, there's this one guy that's from California. And I was like, oh, this guy looks really nice. And he's like near Malibu. And I have this beautiful listing in Malibu. And so, I was like, oh, I spent a lot of time there. And so, I was like, oh, just, you know, in my head. You know how you're like, oh, that's kind of nice. And I wasn't thinking about it. And then he was like starting to chat with me. And I was like, oh, okay. And he's like, we should move over to your cell phone. I was like, my what? You want my cell phone number? Like, how?

How does this work? So I was like, okay. I was like giving myself a number and then he's like, like texting me at night. I was like, like, I'm not a night person. I'm like a morning person. So I was like, why is my phone going off? What is going on? And he was like, blah, blah, blah, whatever.

I have kids. I have all this stuff. And so this goes on for a while. And then I'm at dinner at Bill Bouquet in Sag Harbor. I'm sounding very bougie, you guys. So we're in Sag Harbor at Bill Bouquet, which is a beautiful restaurant. And we're all dressed up because we had gone out for a work dinner. And my two girls were there. And I walk out. He goes, Kelly? And my oldest daughter is like...

And my younger son, I was like, I don't think you know my mom. Like, I don't, we have no idea who you are, basically. Like, she's totally giving him the cold shoulder. And he's like, Kelly? He's like, I met you on Raya. And I'm just like, and like, everyone's just like...

And I was like, oh my God. I was like, hi, yeah, nice to see you. And then my daughter's like, I'm getting ice cream. Bye. And I'm like, I'm just going to go get ice cream. And so like, I literally, I'm awkward. This was the guy? Yeah, don't look at me like that. No, no, I'm joking. This was the guy. This was the guy that I was texting with. Okay. So then whatever, I text him. I didn't text him. My best friend, my friend's like, she texted him and she's like, yeah, so nice to see you. We should...

connect because she's like you gotta like get them to connect right and how long ago is this I need it's like three weeks ago okay happy oh wow this is sounding like a good story to me am I 100% this does not end well no no no hold on so then like I'm like and is this related to Bethany or not yeah we're getting there we're getting there okay so I'm gonna go I'm gonna talk faster okay so

So we're like, I'm like, he's like texting back and forth all this stuff. And then all of a sudden, like, I don't hear from him for a couple of days, but I was like, oh, whatever. Like it's, you know, I'm doing my stuff. And so then it's after Labor Day weekend and I'm in the Hamptons and on Raya, it tells you where people are. I did not know this, but I found out this, that it says like. Visiting. Visiting in wherever. I was like, wow. Oh my God, you know where people are. So that's fun. So he's like, are you in Montauk? And I'm like, I happen to be in Montauk.

doing a photo shoot and he was like let's meet for a drink my kids are leaving and i was like okay so then he i was like oh you know i have to be back in new york so i have to be in new york early and i was like well we can meet for a drink but like i'm driving to montauk and it's spotty in the hampton so i was like it's either now or like basically never so um

You know, and we've been like texting a lot. Like he was like always texting me. And like, so then I was like, I have to leave. Like I can't be in wait for you in Bridgehampton. So a week later, this is very suspenseful. I'm here. I like my friend goes, wait, is this the guy that you were dating? And I'm like, who, what? And it just like sends me page six. And it's like, Brittany, Brittany,

is dating this guy and I'm like wait what I'm like so he's dating her and me so I sent him a text and I'm like I'm like oh I was like the Hamptons is such a beautiful place like I hope you come back I'm really really sorry you are part of the dark side and then he calls me

Call me on the phone. But he was actively dating or is actively dating Bethany Frankel at the same time he's texting with you? Yeah, he said that like that she was like I don't feel like this is going anywhere and so then he started texting me. I'm like, so now I'm like your sloppy seconds? No, thank you. Said no one ever. Like, no, thank you. I'm like, oh my God, hideous. The dating world is so tough. I was going to say, is it that small of a pool to pick from here in New York that that can happen? By the way,

worse than, I mean, first of all, like, like whatever you think about her, like, like her or not like her, every single, like almost, I would say, she's always been so kind and lovely to me, like, on podcasts and through DMs, but yeah. That's amazing for you. Okay.

She's been opposite to me. Oh, no. Awful. I'm so sorry. I love that Jana is just now getting filled in on this. I'm so sorry. She's like my quote unquote like life nemesis. I mean, I knew you guys didn't get along in the show like a million years ago. I didn't know if that was an ongoing thing. No, no. She takes life to another level. It's like whatever she can to get like anything.

She's very thirsty. So cut to, she's like, so I was like, I'll meet a guy and I'll be like going on a date. And he's like, oh, so your best friend? I'm like, I dated her. I'm like, who's my best friend? Really? Wow. Brittany.

And I'm like, wait a minute. I'm sorry, what? I don't know Brittany. It's just a moniker. It's a moniker that was just created. Oh, okay. Got it. So I was just like, wait. We should let other people in on that. I just don't want to say her name. Is that her real name? Brittany? Brittany Frankel? It's just, yeah,

Yes, it is. It's just, you know what? According to me. When you don't have good feelings about someone, I understand this. You just don't want to even give their name power. So you come up with a different name. I've made up names in my book to not give people power. There you go. And legal reasons, but that's besides the point. But were you interested in the guy, genuinely? He's a really nice guy. He has kids my age. That's disappointing. Yeah, and I was like, oh my God. We have similar interests.

And I was like, oh, that would have been fun. But I was like, no. Is he still pursuing you? Well, he gave me this weird phone call, which is kind of like, basically like, if it doesn't work out, I'll let you know. Oh! Also, he's trying to go back to Brittany. Well, I don't know what he was doing, but I was just like, I'm not interested in anything. I'm like, thank you. The only thing that I will say about Raya, which is the piece that I don't like, like, I know that I was...

Some of my friends on the time that I was on Raya, he was matching. Certain people would match with some of my girlfriends. And so we're like, oh, like my girlfriend, Caitlin, she's lovely. And she'll be like, oh, you match with him too. I matched with him. And I'm like, oh, you can totally have them if you want. Like, I don't think that is so wild. But everyone is kind of talking to everyone until it becomes, you know, a thing. So like, I'm not giving him grace whatsoever. Like he was actually in a relationship that's messed up, but I will give grace to the guy where I feel like a lot of guys are called out for,

talking to different people if you're just dating that's the dating world you're talking to different people until I don't know it's just my personal opinion for not totally bashing the dude 100% like listen do I think that he's a bad person no but do I think that he loves housewives yes he knew what he was doing 1000% that's my issue 1000% you can't that's not funny man all he has to do is google and be like her he knew what the hell yeah

He knew exactly what the situation was. And people are Googling people. I don't necessarily like to do that because it's just kind of- I didn't Google you for, I didn't know the drama, so I apologize. I just figured that was kind of show made. I didn't know it was life or not live made. Well, it was supposed to be, but then it was like life made. And I was like, this is so weird. I was like, I don't even know what's going on here. What do you think makes a person thirsty?

- Just constantly going after you for things or just commenting, just genuinely, inherently just mean things. Or going after people that are like, I think one of the things at the very beginning, which we're not talking about, but just like what I don't like in general is that going after people that are like doing good things. Like I don't go after you

to say like, oh my God, like you've had three marriages. I've only had one marriage. I'm better than you. Like, I'm like, oh my God, I have empathy. I'm like, oh my, there must've been something happening. So a thirsty person is someone that like goes after someone who's successful so that they can hop on that success, but then drag that person's success down so that they can kind of prop themselves up.

So that's kind of how I see it. That makes sense. You don't know the full picture of things. Right. And I'm always like, tell me. But I guess from being on television, people just genuinely think that we know everything. I'm always like, listen, if you want me to know your story, you can send your bio to me beforehand and I'll read it. That's how they were. They were like, you don't know everything about me. I'm like, no, I've never even met you before. I'm trying to learn.

you can give me a chance to learn. Kelly, what is the dating world like? You are 56? Yes. Stunning. Gorgeous. Thank you. There's a trend and I'm living it actually right now where women are dating and it's

perfectly acceptable dating younger men. What's your thought on that? And what do you, like when you're looking at who you might date, what do you give as an age range that you'd be willing to date? How low would you go? How high would you go? You know, this is interesting. Number wise. Well, cause like, you know, I always like defer to my kids about everything. Cause it's like, they're my like, you know, life arbiters. And I'm like, okay, so what is it? And they're like, mom,

So like my oldest is 26. She's like, Mom, I'm 26. You can't go to 30. I'm like, I didn't say I was going to 30. She's like, well, some guys at 30 might like you. I'm like, well, OK, but I didn't say that. You said that.

So I think like mid 60s and like, you know, mid 40s is, you know, good. Like, you know, 10 years younger, 10 years older. I think it's like a good thing. I mean, I did date one time one guy that was 15 years younger than me, the nicest human. I mean, he was such a smoke show. God, he was so hot. What happened? It's

I'm so attractive. Why did it end? What happened? What was the reason? Was the age difference an issue? And the nicest person on the planet. It was the prenup, Jenna. He was just too young. He was too young. He was too young. What made it too young? Because he was 15 years younger than me. But was it just the number that was bothering you or was there an actual reason for? It was the number. I just felt like he was just too young. I was just like,

And like I went out to dinner one time with his friends and they were all young and I was like, this is too young. But that's like that, I don't know, but I'm like, I mean I get that, but at the same time, like that Anne Hathaway movie, I'm like, I just, I think there's, I don't want people just to focus on the number. I don't, I love that movie. I thought it was so good. I read the book. I loved the book. I loved it. I ran to that book. It was great. Don't leave. I loved that movie. I did. It was a lot though. He was in his 20s. I mean, but love is love, okay? I don't know. Love is love.

Well, you know what the thing is too? It's 20 years. When I was dating this guy who was 15, who was just so attractive. His name is Alejandro and he's just so attractive. What a name though. You know he's hot with a name like Alejandro. Oh my God, so well-mannered and nice and kind and attractive. He was so nice to my kids when my kids were younger and

I just was like, I knew that he wanted more kids. And I was like, I don't know if that was going to be something that we could do. And, you know, he was also, you know, it was like in his early, he was 30. And so he was like, you know, just trying to like get his life started. And I just didn't think that that was like appropriate.

We have so much more to talk with Kelly about when we continue our conversation. If you are single and ready to find love again, call us at 1-844-4IDOOPOD. That's 844-443-6763. Or you can email us at idopod at iheartradio.com. That's idopod at iheartradio.com. Or you can follow us on Instagram at idopod.

Part two pod. That's I do part two. That's the digit two in the middle there. I do part two pod. And I heart radio podcast. We're falling in love is the main objective. CBS Thursday Academy Award winner. Kathy Bates stars as Matlock in the new CBS original series that critics are calling brilliantly witty with great storytelling and a suspenseful joy ride. You won't be able to take your eyes off Kathy Bates in this reimagining of the original classic.

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When you travel with Road Scholar, you'll be an active learner, not a passive tourist. Every day is thoughtfully planned to open your eyes to new discoveries, ideas, and people. You'll learn from local experts and meet others who share your passions. Find your next adventure at roadscholar.org.