Why You’ll Love Dating an Older Woman

SamanthaDating an older woman is hot. Ask any man who dates one. And as a woman over 35, I’ve never felt more desired by men in their late 20s and early 30s than I do now-moreso even when I was that age. So if you’re only seeking women in the 21-29 age range, let me tell you, you’re missing out. Big time.

So why are men dating these ladies? There’s the ol’ elbow-jabbing, wink-wink idea that cougars* are more likely to put out and pay for everything. Meh, that may be a reason a naïve man attempts to score with an older woman, but not the reason he dates one.


She’s got her own life. And by that I mean: her own career, her own friends, her own apartment, her own money. A 30-year-old man from Brooklyn told me this is what makes independent women a turn on. “I find it comforting to know that her life goes on when I’m not around,” he said. Great if you have a life of YOUR own, i.e., dread clingy girls who abandon their own ships the moment you have sex and set up camp on your shore. Also, the fact that an older woman has her own money means she likely worked very hard to get it. Should you automatically go dutch or expect her to pay? No. In fact, you want to impress someone, take a lady out with some bank because she knows exactly how much that costs.

She can hold her own. This ain’t her first rodeo. So when you take her out with your friends or coworkers, to a wedding or work event, you don’t have to worry she’ll perish without your constant attention. She’s been to enough of these things on her own to manage just fine while you’re talking to someone else. And unlike the 23-year-old who gets tanked and throws shade at your ex, she’s got class. In fact, your ex will likely friend her on FB (like my old bf’s ex-wife did).

She knows what she wants-and doesn’t want. And at this point, she’s not afraid to say it. In the bedroom? Go ahead and try to shock her. Bondage? Bisexual encounters? Threeways? Role play? If she hasn’t tried it herself, she’s likely considered it. If you’re curious about the intimate lives of the older woman, I’m sure the videos over on sexmature.xxx can provide a good insight into what you’re missing out on. But I’m talking outside of it as well. You may buy into the idea that all older women are “desperate,” and some are, but many are not.** She’s choosier, and, unlike the 26-year-olds who think they’ll drop dead if they’re not engaged by 27, married at 28, and prego before 30, she’s looking at life a little differently now. Doesn’t mean she doesn’t want marriage/kids, because she might-but she’ll be pretty clear about it if that’s the case. Since she’s got a little life on her (and maybe even a marriage in her past), she may not have the rigid checklist that a younger girl has. Most of the single women I know over 35 just want a good man, period.

She doesn’t move in a herd. I aw a young man from Queens for a spell who dated older women exclusively because younger woman, he found, couldn’t do a thing without checking in with 15 of her friends. When you date a younger woman, he said, you also date all her friends, and it’s “a pain in the fucking ass.” You can’t just go out and do your own thing because she must check in with a larger governing body. A slightly more mature lady has friends-but she sure as shit doesn’t need to update them with her every move.

She had sex before she had a FB profile. Hard as it may be to imagine a world before Facebook, fact is, there was one-and I, along with many of my lady cohorts, lived in it. Given that we didn’t suckle at that digital teat so early on like female Millennials, we’re not going to live and die by whether we change our relationship status. I even forget it’s there. Get this: I’m not even FB friends with a guy I’m currently seeing. I’ve found it refreshing. It retains a bit of mystery, privacy, for now. I don’t need to be omni-present, liking everything he says or does, and I don’t have to monitor what I say, worrying it’ll be taken a certain way. I did get a glimpse of his page when he left it open one day, and I did take a gander at his ex, but I found it so stressful I closed out of it, thankful every comment from her wasn’t on my daily radar. Try getting away with that with a 27-year-old.

She doesn’t need you; she wants you. If she’s gotten this far on her own, regardless of whatever relationships are behind her, she’s been through the ups and downs to know she can handle just about anything. And she knows she won’t fall into a million pieces if she doesn’t have a boyfriend. But she would love one, for sure. And whereas younger women are putting you through the paces to see if you can provide her with a life, an identity, and a future, an older woman already knows who she is and what she wants to do-she’d just love someone to share it with.

She can make you a better man. A friend of mine dated a 40-year-old woman when he was 22 and new to New York. “She picked the restaurants, paid for things, took me places. She had access to a world I didn’t, and she had done all the things I hadn’t done yet,” he said. Now he’s in his mid 40s, married, with a kid, and remembers that relationship as critical to making him the man he is now. “As a dude, I’m told that I’m supposed to date girls my own age and take care of them, pay for dinner, and so on. But for that period of time, the roles were reversed. She had the power. And it felt great-who doesn’t want to be taken care of? That’s when I understood what it was to be in that role, to be someone’s bitch, essentially. And I could appreciate it when it was my turn to take care of someone else.”


*A note on cougars: The general consensus on cougardom is not so much a specific age as it is who you date. So, if you’re 35 and dating a 37 year old, yeah, not a cougar. But if you’re 35 and dating a 22 year old, ok, you might qualify. As might someone who’s 55 and dating a 30 year old.)

**There is a caveat here: Older doesn’t always mean wiser. And someone who was impossibly needy at 25 may be even moreso at 35, especially if she hasn’t had the relationships she’s wanted. There is, however, some considerable perspective and confidence that comes with age, and the more evolved women will exude it.


Originally published here on The Date Report.