The Guide to Dating Older Women

A misconception by younger inexperienced guys is that older women are not interested in dating them. This simply isn’t true. In fact, depending on the guy, dating a woman 5-10 years older than yourself can actually be much easier and more enjoyable.

The beautiful thing about hooking up with older women is that they have confidence and maturity. These are two qualities in a woman that are really underrated. If she likes you, she’s not going to play games and pretend that she doesn’t. She’s not going to test you as much or make you work for her attention. She’s going to genuinely show that she likes you and if you don’t like her back, then that’s usually fine too. She’s sexually experienced and isn’t nearly as concerned about being considered a “slut” by her friends. Typically if she likes you, she’ll just go straight home with you — no nervousness, no awkwardness. Just excitement and fun.

I’ve always loved hooking up with older women. They have interesting things to talk about and 10 more years of experiences to draw upon. They can teach you things and share interesting ideas. They don’t play games and are usually not dramatic. They’re sexually experienced and very down to earth. The first older woman I hooked up with was 31 when I was 22. Then I hooked up with one who was 35 a few months later, and after that I was definitely sold on the whole cougar thing for a while. A lot of guys go through a cougar phase, which I think is great for young guys looking to build some sexual experience and confidence without having to deal with a lot of the drama that younger women bring with them. 

Anyway, here are some tips and advice specific to guys hooking up with older women. Specifically speaking, this goes for guys in their 20′s looking to hook up women 8+ years older than themselves.

She’s more interested in your sexuality and confidence: Older women are going to be less impressed by your witty lines, your exciting banter, how cool people think you are, etc. They’ve been there, done that, and are frankly bored by it. They’re less impressed by physical looks because they’re used to being hit on by guys 20 years older than you. Their standards in that department are going to be lower. What they ARE attracted to in a younger guy is a younger guy who carries himself with some maturity and confidence. A younger guy who acts beyond his years. One of the first older women I ever slept with told me, “It’s scary how confident you are at 23.” What they want is a young guy that they can look at and think, “In 10 years, he is going to be an amazing man and whichever girl lands him is going to be very, very lucky.” That’s what they’re attracted to in you. That’s what you want them to think. So straighten up and keep the lame dick jokes to yourself.

She’ll be more assertive, so let her be: Like I said, older women are less interested in playing games or pretending to be more/less interested than they actually are. If they like you and if they want to have sex, they’ll probably make it pretty clear and often times they’ll even make the first move. Let them. I know there are some lesser experienced guys who are uncomfortable with this and try to play hard to get, or maybe tease her about kissing them or something. Yeah, this may work to get a 21-year-old college chick all riled up and horny, but a 31-year-old is just going to look at you like you don’t have a dick.

Enjoy her company and be honest: The great thing about older women is that due to their experience and maturity, they don’t take things so seriously. Generally you can be 100% honest with them and they’ll be cool with it. If you want it to just be a one night thing, or if you like them and want to see them again, you can tell them and they’ll respond with calm and grace. You don’t have to worry about any he-said-she-said nonsense, over-dramatic explosions or anything. A lot of times, these women have been to hell and back multiple times with multiple ex-boyfriends. So you coming out and saying that you just like fucking her is not going to ruin her day. In fact, usually that’s all she’s going to be interested in too. Older women are rarely going to see you as relationship material unless you spend a lot of time with them… Which brings me to my last point…

Beware of the back-door marriage trap: If you do end up spending a lot of time with an older woman, and things are great, and there is a real powerful emotional connection… beware. Unfortunately biology cannot be avoided. Not to say that they’re desperate or obsessive about it, but women in their 30′s, once they see you as relationship material are going to want to speed up the relationship timeline quite a bit. Again, they’ve been through the “Oh, we’re just seeing each other,” thing in their 20′s. They’ve had a few multi-year relationships that fell apart. Some of them may even be divorced. They don’t feel like sitting around and “dating” for four years first. Now they’re in their 30′s and if they find themselves falling for a guy, they see no point in sitting around and “dating” at all… I’ve reached this point with two older women, and requests to move in as well of suggestions of marriage and kids were not far behind. Obviously, I was young and not ready for such commitments and so things collapsed spectacularly. From what I’ve seen, this is not uncommon. So don’t be surprised if that amazing 33-year-old you’ve been seeing while you finish up college suddenly wants you to move in with her when you graduate.