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Three Men on Why They Like to Date Women at Least a Decade Older Than Them

Or in the case of one of them, 32 years their senior

If OkCupid is to be believed, the common trope about men being primarily attracted to younger women is no stereotype. The popular dating site has been tracking its users’ age-related habits for years now, and while women are often most attracted to men two to three years older or younger than them, men prefer women between the ages of 20 and 23, regardless of whether they’re 25 or 50 years old themselves. In fact, more than half of the straight conversations on OkCupid are between men and women who are younger than them. And about a quarter of the time, the woman is more than five years younger.

Yet for some men, the allure of the elusive recent college grad is lost. Instead, they prefer the opposite: Older women.

It’s easy to dismiss this attraction as a MILF fetish, but that, too, would be a stereotype — and in this case, a hollow one. Older women are more emotionally mature and self-confident, more steady and successful in their careers, more worldly and chill about the nature of the relationship, these men say. There’s also the part about women being more sexually adventurous as they age.

Indeed, OkCupid urges men to date older women for all the reasons listed above.

To better explore this phenomenon, I interviewed three men who swear by dating older women: a 32-year-old truck driver engaged to a woman 20 years his senior; a 21-year-old IT technician who casually dates 40-something women he meets on dating apps; and a 33-year-old man in a relationship with a woman nearly twice his age.

John Stevens

Job: Truck dispatcher
City: Natchez, Mississippi
Age: 32
Fiancée’s age: 52
Their Story: I never consciously dated older women, it just always worked out that way. But it seems to keep happening, so I must have a preference for them.

It started when I was in college. I was a World of Warcraft nerd, so my college dating life wasn’t much to write home about. But when I was 20, I dated a woman who was 25. It was nice to date a woman who had her own job, her own place, her own money and her own life. There’s a certain confidence to older women that younger women don’t have. For example, when I was 23, I dated a woman who was 29. We went to a computer repair shop, and they tried to screw her over. So she dressed them down, like Clint Eastwood in Unforgiven. That was hot.

My fiancée is a full 20 years older than me, and she’s pretty badass. She owns and rents out a house, and when there’s a plumbing problem, she fixes it. If we have to build a fence for our house, she builds the fence.

We met two years ago when she moved in next door to me. One night we bumped into each other at pub trivia, and I was like, “You’re my neighbor!” She told me she was going to hike the Appalachian Trail, but she wanted to test out her camping gear first. She asked if I’d go with her to try it out. I’d been trying to get my nerd ass outside and exercising more, so I accepted.

I soon realized we had so much in common — e.g., she’s one of the 12 other liberal atheists living in Mississippi. After one hike, I was covered in dirt and sweat and asked her out on an actual date.

“Do you know how old I am?” she asked.

Until that point, I’d never felt love. I’d never been in a relationship that lasted longer than six months. But I started to fall hard for her. She’s the first person I told that I loved them.

And the thing is, she’s more naturally active than I am. I can kayak now because of her. I’m SCUBA certified now, which, if you met me five years ago, you would’ve never thought would happen. I’ve lost nearly 100 pounds since we got together. My walls were bare when I met her. She’s the director of a local art museum, so now I’ve accumulated a sizable art collection.

To me, the age difference isn’t a big deal. Same for my parents and friends, who have been nothing but supportive. Or at least, if they do feel weird about it, they haven’t said anything to me. Who cares anyway? If they snicker behind my back, so be it.

Max Albalate

Job: IT technician
City: Santee, California
Age: 21
Preferred age range: 30 to mid-40s
Their Story: When I was 18, I had a girlfriend who was 25. But now I tend to date women in their 30s and 40s. I’ve dated five women in their 40s, for example. I meet them using Tinder, Bumble and CougarLife, a dating site specifically for older women who want to date young men.

I find older women are often looking for a deeper, more intellectual connection, whereas the women my age tend to only want the most attractive guy. Older women also tend to put less pressure on the relationship. With women my age, I feel like I need to text them constantly; I never feel that obligation with older women.

Sometimes I meet women who don’t realize how young I am — I have a beard and long hair, so people often assume I’m older. When I tell them I’m 21, they get a little hesitant. “It’s just that I’ve never dated anyone younger,” they say. But when I tell them why I prefer dating older women, they’re usually receptive to it.

Most older women are excited about dating a younger guy. I’ve been talking to this 38-year-old woman on Tinder for a few days, and she recently messaged me, “Can I tell you something? I find it really hot you’re only five years older than my son.”

I understand I’m not like my friends my age. I have 21-year-old friends in college who are trying to date 18-year-olds, and here I am trying to date those guys’ moms.


Job: Manufacturing
City: Wyndham, Connecticut
Age: 33
Girlfriend’s age: 65
Their Story: I got married at 21, and after 10 tumultuous years, we got divorced. That’s when I decided to explore my interest in older women. But by then, the fantasy had changed. When I was younger, it was about a woman schooling me about sex. After I divorced, though, it was about me being the experienced boytoy — pleasuring and fulfilling the needs of an older woman. I’d fantasize about being a handyman or pool boy, and doing work for an older housewife.

Anyway, after the divorce, I moved into a new house. One night, I noticed my neighbor’s mother at a party she was having. Her mom immediately caught my eye. It was like cliché love at first sight. I’d been drinking a little, so I had some liquid confidence and started talking to her. She was a strong, independent woman who was very self-confident.

Eventually, someone came around and offered us virgin Jello shots.

“So you’re just offering us Jello?” I replied. She laughed at that.

She told me how she needed someone to come over and do some handiwork, and I readily offered my services. I think I even said, “You won’t even have to pay me in cash.”

I got her number, and we began texting. At first, she kept trying to find every reason for it not to work between us. But I’m good expressing myself in writing — much better than I am when speaking, actually — and I was able to show her that I was genuinely interested in her and wanted to give it a legitimate shot.

A year and half later, we’re still together. She looks 15 years younger than her age, and she’s youthful, athletic and always doing stuff. I’ll be the one sitting home on a Saturday night, and she’ll be texting me how she’s on her way back, because she’s always out at social events. She’s a free spirit, and even at her age, she still always manages to see the good in people. In general, she’s just a very loving person with a fantastic heart.

At first, my neighbor was skeptical of me trying to date her mom. Maybe she thought I was cougar hunting or something. But she’s since come around. When my girlfriend’s husband died, my neighbor was worried her mom would never love again, and spend the rest of her years sad and alone. So she was happy that her mom and I found each other. “You make her smile,” my neighbor has told me.

My girlfriend’s nephews are all former military guys in their 40s, so they’re older than I am. But we managed to win them over, too. At first they thought it was weird she was dating someone younger than her kids. But soon after they saw how happy we were together, they said, “We get it. You don’t have to explain.”

Every once in awhile, my girlfriend will ask me, “Are you sure you don’t want to date someone your own age?” And I always tell her, “No way, I don’t want to go back to that.”

*Name has been changed to protect the innocent.