culture

4 Women on Dating Younger Men

Photo: A24

Get your glass of milk ready: The long-anticipated release of the erotic thriller Babygirl is finally here. The film follows a high-strung CEO (Nicole Kidman) who enters into a steamy and illicit affair with a hot young intern (Harris Dickinson) who seems to know exactly how badly she wants to be told what to do. Many, many orgasms follow. Though the whole film is a whopping HR violation, there’s little foreboding in Babygirl, which instead presents the older-woman–younger-man dynamic as a space of raw sexual exploration. But what are the dynamics like when you’re actually sleeping with a younger man? We spoke with four women in their 40s and 50s (some of whose names have been changed) about navigating the ins-and-outs of age-gap relationships, from the uncomfortable gendered stigma to the office hookups.

“We were at such different stages: Why would a 20-something be interested in someone hurtling into their 40s?”

I met my husband at work. He was 24, I was 34. He was an assistant, but I wasn’t his boss, and didn’t make decisions about how much money he made, his hiring and firing, or anything like that. We became work friends, and though I noticed he was interested in me, I chalked it up to him wanting to learn about our field. We were friends for a year or two and had hung out in co-worker groups before things ramped up and I really noticed him flirting with me. He’d text me outside of work hours. There was an IT guy at our office who clearly had a crush on me, and he’d say things like, “Well, he’s not wrong about that.I told him about a hookup with someone younger than me, and he goes,You should try dating someone who’s 26, which was the exact age he was. But it was so far from my mind that I didn’t think it could be on his. After all, I met him when he was freshly out of college, and his social life revolved around going to clubs with friends and girls in their 20s. Meanwhile, I was in my 30s and just out of a five-year relationship. We were at such different stages: Why would a 20-something be interested in someone hurtling into their 40s?

We started dating. It was a secret because of work, but eventually they found out. He switched workstations with someone else but was still logged into his personal account. The other person found a message from him to me that was clearly not professional and reported it to the company. It was mortifying, but everything turned out fine. We had to meet with HR and sign some paperwork saying he couldn’t do any work for me. Eventually, he left to do other stuff — it was kind of a starter job for him. It was scandalous at the time because of our age difference, but nobody was surprised. We’d been eating lunch together every day and took the same bus into the office. People were like, “Do you guys carpool?” We were like, “Kind of.” 

I had some reservations over the age difference at first. Friends who knew about us were like, “What the fuck are you doing?” My family was skeptical too. I thought, Maybe he’s just into this sexy idea of an older, seemingly powerful woman. I had no experience with younger men and had this idea of them growing up on pornography, with totally different views about women and relationships than someone like me, who is on the cusp of Gen X. I figured there was no way he could be serious about this. But I thought I’d just see what happens.

We moved in together after about a year of officially dating, when I was 37, and started talking about marriage. I was like, “You’re not even 30 yet; do you want to have a child someday?” Because my time for that has an end in sight. We decided to give it a shot when I turned 39, and I immediately got pregnant with our son. We got engaged during my pregnancy. For all the drama of our early years, we now have a completely normal married life. We go to Costco on the weekends. We garden. Now that my husband is in his mid-30s and I’m in my mid-40s, the age gap doesn’t feel as pronounced. But I look back at old pictures of us and go, Oh my God, you look like such a baby. — Sarah, 44, Seattle

“The post office is known for hookups, and I don’t think anyone was surprised, though the fact that it’s kind of a secret is fun.”

I’m 41; he’s 28. Before him, I never dated younger; most of my boyfriends have been right around my age. We’ve been hooking up on-and-off for about a year. We both work at a sorting facility at the post office and met while working overnights. I’m a lead clerk, and he’s a mail handler. When you work overnights, you make friends with whoever’s on shift. So we became friends and joked around, but I did that with a lot of people. He was just a really sweet, understanding guy with very nice eyes. At the post office, people tend to be negative and complain a lot. He wasn’t like that. He was a Hey, let’s have a good day kind of person.

Last year on his birthday, he said he didn’t have anything to do, so I was like, Let’s get together and throw him a birthday party. We invited a few people over to his house. A few showed up. I ended up having too much to drink, and we started hooking up. The next morning we woke up and decided we probably shouldn’t do that again. A few days later, we were like, “Okay, let’s do this again.”

One of the reasons I kept going over there was because he made me feel really comfortable, needed, and wanted. And the sex was great. The sex is actually a lot gentler than with an older man. At first I had to lead him, but eventually he opened up and showed me a few of his talents, too. I definitely go back to him whenever I need an ego boost. Would I be in a relationship with him if I could? Probably. But he doesn’t want one and I’m just not built for them anymore. I’ve been through a lot of trauma in my life, and he meets the basic standards that a lot of men haven’t in the past: He’s willing to listen to me, to let me cry it out. When it comes to my kids, he’ll ask: “Hey, how are they doing? How’s the project at school?” 

A few people know at work, but that was bound to happen. The post office is known for hookups, and I don’t think anyone was surprised, though the fact that it is kind of a secret is fun. I worried he might need me to do motherly things and fill the older woman role, coddling him and being like “Okay, okay sweetheart,” but that hasn’t been the case. I did end up doing the dishes and his laundry a couple of times, but that was more my anxious energy and nothing he really asked of me. My oldest daughter is 18 and has met him; we played Cards Against Humanity at his house. She’s kind of judgy — she’s got that, I’m the oldest girl, I’ve got to keep my eye out and make sure things are okay thing — but they got along. — Emma, 41, Kansas

“I’m five years younger than his parents, so conversations at the dinner table are always easy.”

In 2018, after my divorce, I’d just moved from London to the country when I came across a man 12 years my junior on a dating site. He was an old soul, and we stumbled into a relationship, my first with a younger man. When we split up a couple years later, I started thinking that I wanted to date younger as well as older. I thought, I’m established, I’ve got everything I need financially. I don’t want any more children or someone to provide for me. I did that for myself. I just want an equal partner.

I spent about three years dating in the age-gap pool and met people through Bumble, Tinder, and local websites. I dated people my age, younger, and older. To be honest, many of the guys in their 50s couldn’t keep up, and I don’t mean in the bedroom: Literally, my energy level was so much higher. I have an active lifestyle and a busy work life. I went through a gamut of younger men who see older women as a sex object or something for their bucket list; the time-wasters, the men with the mommy issues. I got burned out and took myself off all the sites. That’s when my now-partner sent me a message on Reddit, where he’d seen a random picture of me. He wrote the worst pickup line imaginable — “Hey, maybe if I was a fireman, I’d put you out.” I responded and said, “Look, I’m more than willing to talk, but I don’t want to date.He said he respected that and we became friends. We talked every day; he sent me stupid memes. He was 30 and I was 48.

Later on, one of his best friends told me that even when my partner was in secondary school he was always more interested in the teacher than the students — everybody knew he’d end up with an older woman. After a few months of talking, he told me he’d like to meet in person. We lived five hours away from each other, and I told him he could come and meet me but had to stay in a hotel, which he did. We didn’t do anything sexual, just hung out in a beautiful part of the country. We kissed, but there was no chemistry. As he was about to leave he was like, “Can I see you again?” A couple weeks later, he visited me during a work trip. I came into the room and saw rose petals all over the place. It was cute, but again, nothing physical happened and he was respectful. A few months later he said, look, “We’ve been talking for months, and I’m really interested in you. I was always told younger men are only interested in sex or that people of his generation have sex really quickly, but it wasn’t like that. He’s more respectful than anyone I’ve ever been with. I figured, All right, this guy isn’t just in it for a physical relationship. No one would wait so long.

Since I’ve met him, he’s moved out of his parents’ house and bought his own property and is doing okay at work. We bought our first house together this summer and are talking about getting married. I’ve got a teenager, so we’re making slow and calculated plans to be together. We occasionally get looks when we’re out in public, but I laugh about it. When he shaves, he looks even younger than his age. Once, I was dropping him off for the train into London and loudly said good-bye. The train guard goes, “Oh, it’s lovely you took your son to university.I’ve had friends say to me — especially friends with sons — “Why would you do that?” I think they were genuinely afraid I was a bit of a predator. I’m like, “No, my partner’s 30.” Sex with him is tender, and he’s respectful of how my body has changed with aging. He’s always only been intimate with older women.

There’s a lot of vitriol toward older women who date younger. Society will joke about Leonardo DiCaprio, but when it’s a woman who’s hit menopause or is close to it, it’s almost always like, “You’re dried up, and that poor man is missing out on the ability to have children.” My partner doesn’t want children. My past relationships with younger men haven’t lasted because they did, so there was always an expiration date. My partner and I have a nearly two-decade difference, but we don’t notice it. (The only difference I do notice is that my partner is a gamer, but that works well for my teenager, because now they game together.) I’m five years younger than his parents, so conversations at the dinner table are always easy. He’s got more energy than I do, which you’d expect, and I’m financially further in my career, so we divide everything in a balanced way; he pays 25 percent, I pay 75 percent. Our dynamic may change when I retire and he’ll have to provide for us more, but that’s the same for any couple with a difference in age. Sometimes there are stares, but it’s only a thing if someone makes it a thing. —Cameron, 50, England

“You got to go handle your mommy issues, because I’m not the one.”

I’m 51, and my partner is 36. We’re poly, and he just moved in with me and my husband. My husband and I are close in age and have been married for 17 years; we actually met on Yahoo Personals. At first we decided to be monogamous — he’d asked me if I wanted to do poly-type stuff, and I was not in the right head space for it — but down the line he had an accident that hurt his spine and basically left him disabled. I’m a sexual creature, and two years into the marriage, he no longer was. I was like, “We have to fix this scenario because I’m frustrated and taking it out on you.” We opened up our relationship in 2010. I’ve had several relationships since, and almost all of my partners have been younger.

I ended up meeting my current partner six years ago, on a Facebook polyamory group, when he was 29 and I was 45. He reached out after seeing my picture and lived near me, which is rare in a group like that. When I looked at his profile I thought, He definitely looks young. We started talking, and he was the sweetest guy; we had so much in common and texted back and forth. I had a blast.

We continued talking and hanging out. My father and brother had recently passed away, and I was depressed. It was a rough time, but he was there for me every step of the way. He was like, “Make sure you eat. Text me after you do.” He was so supportive. I hear women say they’re afraid to date younger guys, that they’re so childish, they’re not ever going to know what I’m talking about. I’m sure that happens, but it’s never happened for me personally. He’s an old soul, an old-fashioned gentleman. And the intimacy is fantastic. I may have some issues down the road because, well, I’m 51 now and in menopause. But so far, it hasn’t affected me. I still have a really high sex drive, and he loves that he’s finally found a woman with a sex drive that’s similar to his. We have the same kinds of kinks, and he loves that I can keep up with him. (I’m submissive, he’s dominant; we enjoy role play and costumes.) We have no complaints so far.

Younger men have better stamina in bed and tend to be in better physical shape than men in their 50s and older. Many, if not most, of the men my age are experiencing erectile dysfunction; the ones who aren’t tend to be selfish in bed. They often don’t take direction very well. I also find younger men to be more open to incorporating toys in the bedroom: A lot of the older men view them as a threat to their manhood or something. And these millennials are much more emotionally intelligent than a lot of the older men out there. They’ve often had therapy at some point and have healed the issues that older generations simply refuse to acknowledge, let alone address.

People assume a lot about women who date younger. That you’re desperate, that you hit the wall at 30. Maybe you hit the wall at 30. If I get all dressed up, trust and believe younger dudes and older dudes are definitely feeling it. But I do have a loose rule: I don’t intend to date anyone less than 30 years old at this point in my life. First of all, my nephew is 32, and I’m like, No thanks, I wiped your ass. I get hit on by 19-year-olds constantly, and I’m like, Guy, you got to go handle your mommy issues, because I’m not the one. —Sharon, 51, Buffalo

4 Women on Dating Younger Men