Forget Your Ex! Younger Men Want Older Women!

0:03 Thank you. Hey, I do part two. It's your celebrity mentor, Kelly Ben-Simone. Today, I wanted to dive into a very hot topic. I'm seeing it everywhere right now. Women are dating younger men in their chapter two. I've done it myself, and I think it can be really liberating. So... There's a lot of celebrity women in their chapter two that are experiencing these positive vibes of dating younger men. I mean, here's the list. Like Kris Jenner, she's 70. Corey Gamble, her boyfriend's 45. Jessica Simpson, we just found out she's 46.

0:55 Her boyfriend, Thomas Eisenhower, is 33. Jessica Alba, she's 45. Danny Ramirez is 34. Cher, 79. Alexander Edwards is 39. Love that. Madonna is 68 and Akeem Morris is 30. So we have seen so many of these beautiful women that are in this chapter two, loving life and having the best time with these men. And they are seriously strong, iconic women and good examples. So let's dive into it.

1:29 My first experience of dating a younger guy is 10 years younger than me and very smart and a go-getter. And I really, really loved being around him and I loved his energy. This was right after my divorce. My ex-husband was almost close to 30 years older than me. So it was just a nice foil to... what I dealt with before. And I really like the energy and I just like the mindset. I'm a very curious human and I am always looking to do things in a different way and I'm very open to learning. I mean, some people are like, this is how I do it.

2:10 This is my mindset. This is what I'm doing. And I'm not like that. I'm always asking people their advice. I'm always asking people their opinions. And I just want to learn. And so that's just really important to me. And I met him through a mutual friend. And so I was like, okay, this is fine. I didn't meet him at a bar. I met him through a friend.

2:30 So that was fine. So it was just interesting because at first I was a little nervous. I was like, oh my God, he's 10 years younger than me. Like, what are people going to think? And it's not like I was like, you know, I was 37. So I was just very nervous about what other people thought. And I honestly don't know why, not looking back at it. But, you know, people, when they would see us together, we didn't look, I mean, I always had two kids, but we didn't look like there was an age difference. And because I look younger than I am and he looked a little bit older than he did. So it was, we actually kind of matched in energy and looks. It was just funny how people that I knew, some were like my, you know, some of my friends were just like,

3:18 do you Kelly and have the best time. And other people were like, I'm not going to hang out with you. You're going to date a younger guy. Who is this person? And I was just like, I'm just having some fun and you should celebrate your friends having a good time. And I think that that's something that's like women are afraid of is that they're afraid that their friend group are going to judge them for taking a gamble on something that's totally different. And especially for me, my ex-husband was a homebody. When we were home, he was at home.

3:49 And when he was gone, he was gone. So I was by myself. I was home. And so I just wanted to... And men do it all the time. And I just wanted to do something. I actually didn't want to do anything. He literally just fell into my lap. The universe was like, here he is, have some fun. And I was like, okay. But there is such a double standard. And I think it's a double standard because when men and women get divorced... women process things maybe a little bit more differently or maybe more hyper emotional than men, you know, are considered, you know, now. I mean, obviously men have feelings and it's just the way that they articulate them is different. And, you know, women, we need our friend groups and we need our venting sessions

4:41 and we need to be able to talk through things. And men just really aren't like that so much. That's a generalization, clearly, but that's my opinion. And I just feel like a lot of people, the majority of my friend group, were very, very judgmental. It's funny because I was talking to Luann, was describing how when she met me on The Golden Life on E!, which comes out every Tuesday at 10 p.m., and she was like, well, when I met Kelly, I met her in St. Barts.

5:10 And I was so upset with my marriage, and she was with this hot guy, And I was so jealous of her. And I was like, okay, well, how to be happy that I'm with someone that's fun because I just spent the last 10 years of my life locked up like Cinderella. So maybe it's okay to enjoy your life and have a good time. And I didn't see anything wrong with that. So when it came to dating this younger guy, You know, it's like, I felt like Stella got her groove back. I felt really beautiful and I hadn't felt beautiful in a long time. And I just looked at myself differently and I worked differently and I accepted jobs that I wouldn't have. You know, like I auditioned for a James Bond movie, because I was like,

6:03 I could do this. Why not? I probably wouldn't have done that if I was, while I was married, I would have been like, no, no, no, I can't do that. That's not for me. So I was just doing things that were different as well. And it was just really, really good for my self-confidence and for my ego. And it just, you know, I really suggest dating someone or just what we were talking about before, kind of practicing dating, experimenting and dating all different kinds of ages because After I dated him, I dated a guy that was 15 years younger than me, and he was, like, an incredible human.

6:40 I mean, he is someone, like, he was just an incredible human. I was, he was 15 years younger than me, and I was 45. And... He was kind, considerate, well-educated, well-mannered, beautiful to my kids, loving and nurturing to me. Very, very, very sweet. And I had gone through, I met him actually on Facebook. I was getting my MBA and I had my computer open. I was getting my MBA online at 45 and I had my computer open. And this guy is like on Facebook. I'm not like really a big, I mean, I work in social media, but I'm not like a social media person. I don't like use it to communicate. And I was like, wait a minute, this guy is like texting me over Facebook, messaging me. And so he was like, I want to meet you. And

7:37 I'm like, I'm kind of studying right now. I'm a little busy. And because I was cramming my MBA, trying to cram it into a year and a half. And He was just like, no, no, I want to meet you. So I met him at a bar in New York. And my best friend was literally sitting down on the table next to us to kind of see if everything was okay. And he was very, very handsome, very attractive, very well-educated, again, very well-mannered, just sweetest, sweetest guy. And I adored him. I mean, I was like, this is my guy. This is my person. Except for one thing.

8:14 He wanted more kids. And I was 45. And I was just like, how is this going to happen? How am I going to take this to the next chapter? Am I going to have another baby at 45 years old? I literally was like psyching myself out and had this narrative in my head about what it would be like to have a child at 45 years old. And I think that is one of the negatives of dating a younger guy is that you want them to have a beautiful life just like you did. I did I wanted them to have everything and I want them to make their mistakes and I want them to learn from them and I wanted them to be in a position where they could I didn't want them to resent me because they were with me and they and you know a part of their life was gone like I you know

9:04 resented my the first guy that I dated who was younger because I wanted to have more kids and And it was just, it could just, it never was able to get to a point where it was something that I felt secure about. And so I resented him for that. The second guy, younger guy, I feel like I'm like this wild woman. He was 15 years younger than me.

9:29 And I reached out to him literally this year, just because I've gone through a lot of health issues, physical, I got brain concussion. And I was just like, you know, let me just reach out and just say hello. Just how are you? And I tried to like text him. And then I asked a friend about him and he lives in Italy and he has a baby and he's a rock star. And he's, you know, completely different life than what he was. doing with me. So, isn't that just so crazy? It was very sad. And then I dated another guy that was 10 years younger than me who I really, really liked and I felt like I didn't date a lot of guys because I was like, oh, these guys are like, I felt comfortable in that 10-year relationship to my junior vibe. I felt very, very comfortable.

10:22 I didn't feel intimidated. I didn't see, I just felt, I just felt that older guys, when I was going on dates with older guys, I just felt that they weren't, they just wanted to go out with someone that was famous and someone that was pretty. I don't, I didn't feel like they wanted to have any kind of like true connectivity. And so when I would go out with younger guys, they couldn't care less like what I was doing.

10:46 They're like, okay, that's great for you. And the shows that they weren't watching and they didn't even care. So the third guy, I really, really liked him a lot. And we broke up because I had just filmed Scary Island on Bravo for Real Housewives. And I just said to him, I really care about you so much. And I'm going to have to break up with you because I cannot subject you to to anything that happens online that could be bad because people are going to be like, you're with that girl, the fall girl. She took the heat for everything. And why did she do all that?

11:30 I mean, I did it for a reason because it's my job, but I really felt badly for him. So looking back, I texted him again too this year. And I was like, hey, do you want to talk? And he's like, no, I'm good. I'm great with my life. I don't want to talk. I was like, I get it. I wasn't really the nicest person to break up with.

11:58 And I did hurt their feelings, but I didn't hurt their feelings for the wrong reason. I broke up with them. Each one of them, I broke up with them for the right reasons. The first one, because it just wasn't going anywhere. The second one, because I knew he deserved a bigger life that I couldn't offer him. So yeah, so I broke up with those guys for all the right reasons. I mean, I know that I hurt them and I hurt myself too, but I also understand when things are moving forward and going to be good for everyone.

12:31 I understand that. And my last boyfriend was 50 years old and younger boyfriend that was 50 years old. And at this point, I'm just like, I know what's good and I know what's not good. And I hope that they're all super happy. And sorry if you're listening and I hurt your feelings, but I'm sorry. But I did it for the right reasons. So now let's talk about the pros and cons of dating guys. So the pros.

13:05 First of all, if a younger guy, I was doing some research, and if a younger guy dates an older woman, he actually lives a longer life. So I thought that was actually interesting. And I was like, wait a minute, what about the women? Do they live longer lives too? But actually it's really, really good for younger men to be with older women. It's really healthy for them. But I really liked what we do. We outlive men too.

13:32 So it's part of that, but it is really, really good for their longevity. And I think it's because they can younger guys, when they're with an older woman, they can just be themselves. And we're accepting of who they are. We know they're younger. We know they're in their velocity era. We know that they're trying different things. So I just really have always been a possibility person with my male friendships, my female friendships. Like I just have always been like, I see a possibility in someone and I try to nurture that. I'm a fixer. And so I just really, I'm also an avoidant fixer. That's a new term. So maybe that's one reason that I like younger men too, is because I don't feel like I'm, that I don't

14:22 have to do anything. I can just continue on my life and there's no expectations. I haven't had been with the guy that where I really thought there was going to be expectations outside of the one guy that was 15 years younger than me. I mean, I think with a younger guy, obviously they can be attractive, but older guys can be attractive as well. It's just a different kind of look. I personally like the playfulness because I work in a transaction business with a lot of very aggressive men. So I like when men are playful with me.

15:01 I don't like when they're aggressive because that's my work life. And I... I just like the spontaneity. I love that they're just like, let's, you know, it's a beautiful day. Let's go get a beer. Like, I just love it. Or bring Tarzan. Let's go on a walk. I just love that kind of, or, you know, let's just go to that party that you have to go to and then just walk around and just see where the night takes us. Like, I just love that kind of vibe versus being with like an older guy. They're just much more like, The party's at seven. We're going to be there until eight. I need to be in bed. I need to work out in the morning. I'm going to the club in the morning, working out or whatever they're doing.

15:40 They're just more, for lack of a better word, just more rigid in their mindset and how they're living their lives. And no harm, no foul. It's like they've been living it this way. This is how it works. But a younger guy is just more like, hey, let's try it and see what happens. And I think that's really, I think there's nothing wrong with older women dating younger men.

16:04 And I want to hear about every single story about all you guys dating younger men. I have some news for you that I kind of changed my mindset about dating. And before I was like, I want to get married. I want children. I wanted to have more children. I always wanted to have more children. That's why originally why I got divorced because I just like, I want more children.

16:26 I want a family for my family. And that just never worked out for me. Um, and now I was just so adamant for so long about, I want a family for my family. My children don't deserve this beautiful family, but they have a beautiful family. They have me, they have my twin brother, they have my father help, you know, who's helping to nurture them. They have all of my male friends in their lives who adore them. And they just have such, they live in such a warm, loving environment that, um, I don't really have that feeling anymore.

17:01 And then after having two health issues this year, I just really decided that I just want to live my life and whoever wins, wins. I don't care how old they are. I don't care what they do. I mean, obviously they have to have They have to have a certain financial wherewithal because that's just not fair to me.

17:28 But I definitely am open to just living my best life and seeing what happens. So when it comes to some of the negatives of dating a younger man, there's a couple of things to think about. Number one, and this happens on 90 Day Fiancé all the time, that one of the partners is not financially stable. And so if you're an older woman with a partner who's not financially stable, it's very, very, very taxing on, you know, it would be very taxing on me because I would constantly be trying to think of like how I could help them, but then I wouldn't be focused on what I'm doing for myself. And at this point in my life, I've already raised two beautiful children and I need to be with a partner in crime and not with someone

18:19 that I am, raising or nurturing. And number two, and this happened, this was what I used to think about all the time. I'd be like, why would, I would literally, this is awful thing, but I'm going to tell you is that I would walk down the street and I would see a really pretty girl and I would be like, oh my God, I was like, that's something, that's someone that my boyfriend at the time should be with. And that's not cool. And it's awful to think like that.

18:47 And sometimes they do leave you for younger girls. And there's nothing wrong with that. I mean, there's nothing wrong with finding your person no matter what age, but that is always in the back of your head. And I know it's in the back of a lot of men's heads as well. They're just like, well, she's just with me right now, like an older guy or the young girl, she's just with me right now for my money or she's just here for the fun and then they just never move forward and then you put time, effort and resources into somebody, this doesn't happen. So, if you're going to date someone that's younger, you just have to be open to it. You have to just be like, I'm just going to date this person. I'm just going to

19:34 date these people. And I'm not going to put any expectations on it. And I'm not going to put any expectations on myself. I'm not going to look at my skin and be like, oh my God, he's going to see that my, you know, 58 year old skin looks like this or whatever. Um, So my age range, I was like, at first I was like, maybe I should, maybe I should jack it up to 70. So my age range is 45 to 65, I think is a really good, like I think those are, that's a good range for me. Like not, not 40 is I think is too young. for me um but I definitely like 45 I could date and 65 I could date but not I don't know if I could date older than that I thought I could date 70 but I don't know if I can I don't know I've never met

20:22 I haven't really met anyone that's 70 yet but I am on the golden life so you never know what's gonna happen Enough about me. I have a great friend who's going to come on and he's going to talk to us about actually dating and has married a younger guy. Stay tuned. Jenny, Jenny, my favorite Midwestern girl.

20:58 Kelly, Kelly.

21:00 I have a hot topic that I need to talk to you about.

21:04 Tell me.

21:05 It is about older women dating and or marrying younger men.

21:12 Well, I don't know anything about that, Kelly.

21:18 That's what I wanted to ask you.

21:20 My husband, well, we dated for like three months and then we got married at six months.

21:25 Wait, I love that. Three months and then six months. Yeah.

21:29 He's nine years my, what's that called?

21:35 Junior.

21:36 He's nine years my junior.

21:38 Yeah. I love that. Have you ever been in a relationship with a younger guy before him?

21:45 No. No.

21:47 He was the first.

21:48 I mean, yeah, because I was just around people my own age my whole life.

21:51 Right.

21:51 I always thought maybe I would date somebody older.

21:53 Right.

21:54 But then, you know, you can't, when Cupid comes a-calling, what are you going to do?

22:00 100%. Did you know he was younger when you met him?

22:03 Yes, I did. I knew he was younger, and I was literally just trying it out. I was kind of at that stage in my life where I was going to, practice dating because i'd never done it so he was supposed to be just a practice date and then you end up being your husband yeah well there was just such he brought such a um an energy into the room into the relationship and you know it and i think there was something to the fact that i had already done it once twice um and he had never been married and So he was like eyes wide open and like, this is so great and exciting and oh my gosh. And so I wanted to get married to him, not just for myself, but for him, for the fun and levity that he brought into our home. And there's

22:56 good and there's bad when you're dating or marrying a younger person.

23:02 I love that you're talking about the levity and the fun, because you've already done it. You have your beautiful children, you have your life, and you just wanted to enjoy your life. And I think that's one of the things that's so great about dating a younger guy. I'm kind of shocked. It was like you dated for three months and six months you got married. Do you think that that's typical where younger guys are just like, okay, this is what I want and I'm ready to go?

23:30 I guess so, but I don't know if that's like naivete or just, you know, like they don't think things through quite as much as an older guy would. More like just like jumping in and let's see what happens. But I do think that, like I said, it comes with its pros and its cons because you have to make sure you're marrying someone that, and they hate hearing this, but that you see potential in. So when you're marrying someone that's younger, you can look at the man they're going to be in 10 years, in 15, in 20 years.

24:03 And you have to know that that person has the capacity to grow and like to evolve. Because if they're just still, you know, acting like a child and acting like a frat boy, then you probably should not waste your time. But if you can see that like nugget of a good man in there.

24:21 Right. I love that nugget.

24:25 There's a chance that you could grow together in this beautiful way.

24:29 So I was wondering, does being with a younger man, obviously he matches your energy and that was something that you really liked? He does.

24:37 I don't think he can keep up with me.

24:39 I was going to say that. I was like, I can't.

24:43 No, he can't keep up with me. We were just talking about last night, actually. And I was like, look, this is who I am.

24:48 I go.

24:48 I think of things.

24:49 I do things.

24:50 I act. He's kind of like an old man in a younger man's body. Which it works and it doesn't work because I'm a homebody. So I like staying home. And he does too. We like our routines. But I'm much more like, I like spontaneity as well. So it's hard to say who's bringing what to the relationship at this point. But we always have a good time together.

25:19 I love the partner in crime kind of vibe where you're just together and you're having a good time and he does his work and you're doing your work.

25:27 And you're so much more confident as you get older that you are busy doing your thing and your work and reaching your goals. And he's working to reach his goals too. And to figure it all out.

25:42 Yeah.

25:43 And sometimes the gap, the nine-year gap, really shows itself.

25:47 And sometimes it doesn't. Like television shows or like how?

25:51 Well, just developmentally and like career. I think that's where I see it sometimes. You know, he's much more like, you only live once and I'd rather go golfing than, you know, focus on work today.

26:09 Yeah. And that's his choice. Like, okay, great. If that works for you, great. But I have a little.

26:13 Bit more of like a got to work hard all the time and keep going, keep pushing.

26:18 I think that's our Midwestern vibe. Probably. We want to eat. Right, exactly. We have to do it well. We have to do it well. So do you think that women should experiment with younger men in their chapter too? Yeah, absolutely.

26:32 I mean, if you don't do that now, you're going to miss out on knowing anything about it.

26:37 Right.

26:38 So yeah, try it out. But like I said, look for a guy that has that nugget of what you see as potential, what you know is going to be a good man at the end of the day because you don't want to put all your energy into, you certainly don't want to raise this guy. You certainly don't want to be his mommy. You have to make that very clear from the beginning because the younger guy's tendency is to be like, oh mommy figure it feels so good to be you know around you taking care of you i feel like safe there but yeah no that doesn't work in the in the end um i don't want to be anybody's mommy except my girls.

27:15 No so exactly and you've already done that yeah oh.

27:18 My god make sure that the guy you know he's he's got his own path right he's not just hooking his train onto yours.

27:27 I love that. That's perfect advice, Jenny. Of course, always. You have such good advice. And I love seeing you.

27:34 I saw you on a magazine. I was like, oh, there's my friend.

27:37 I hope I see you soon.

27:41 Okay, ladies, go for it.

27:42 Don't hold back. All right. Bye.

27:45 Bye, Jenny.

27:46 Thank you so much, Jenny. I really appreciate how honest and beautiful you are. Are you dating someone younger in your chapter two? How's it going? Send us an email or leave us a voicemail. All the info is in the show notes. Follow us always on socials. I do part two and I Heart Radio podcast. where falling in love is always the main objective. And don't forget to follow me every single Tuesday on E! on The Golden Life.

28:19 I'm in my velocity era. Let's get golden!