Pause, Cougar! What You Need To Know Before Dating A Cub

Romantically involved with a boyish type? Decide whether it's "for fun" or something more serious.

By Kara Oh — Written on Aug 15, 2013

Relationship Advice For Women: Dating Younger Men

One of the members of my Inner Circle asked me to write about being an older woman involved with a younger man because she's dating someone younger. I guess I'm kind of an expert in this arena because I've been involved with a younger man for the past two and a half years. He's 40 and I'm 63. He's 23 years younger, which is probably a bigger gap than most couples.

The crazy thing is how perfectly suited we are to each other and how well we match on every level, even though, on the surface, it would seem like we'd have very little in common. One thing that works in our favor is that I wanted a younger man (although I was thinking more like 48) and he prefers older women (he pursued me and knew how old I was, because he first set eyes on me at my 60th birthday party at the tennis club where he worked as a trainer).

It turns out that one-sixth of women in their 50s prefer men in their 40s. Who knew!

I knew I wanted a younger man, but only as a playmate. I was hoping for someone to have great sex with, to join on dates and take a vacation with a couple of times a year. Even when Stephen and I first got together, I assumed it would be temporary. As of tomorrow, we'll have been living together for two and a half years. And the crazy thing is, we marvel that it continues to get better with each passing month.

One thing that worked is that I told him we should just let things unfold in their own way and in their own time and when one of us no longer wants to be in the relationship, then we'll become friends. But then, that's the advice I give to all couples. The moment that pressure from either side enters, the one resisting usually resists even more. Men who enjoy older women do tend to be more settled and open-minded. But there are some things to consider before you get too emotionally involved.

Here's my checklist for deciding on whether your "younger" man is someone you want as just a playmate, or a serious, long-term relationship.

Stage Of Life
Life Experience
Interests And Activities
Education
Perspective On Life

Now let's go into some detail about what you need to be looking for in each of these categories.

1. Stage Of Life
This will probably be the biggest consideration for you. If he's in his twenties and you're in your thirties or forties, there's a huge difference in what stage of life each of you are in. Men in their twenties are still pretty much boys. They see life as a big playground, seeking out new experiences and adventures. They may say they want to be in a relationship, but they don't yet know quite what that means.

For them, being in a relationship is more about having someone to go out with and to have sex with. They're not ready to settle down (meaning, stop with the new experiences, already!) and they certainly aren't ready for marriage and babies. Once a man is in his late thirties, and especially into his forties, he's got a much better idea of what being in a long-term committed relationship is all about. He knows much more clearly if that's what he wants. So take what stage of life he's in very seriously because if he's still "sowing his oats" and you're wanting the coziness of a committed relationship, you're probably not a good match.

2. Life Experience
No matter what his age, if he hasn't done anything "grown-up" and you have, then you might not be able to make things work. If he's never been married, had kids, been in a serious, long-term relationship, or had any real-life responsibilities, and you have, then this is likely to cause a problem.

If you've learned to be responsible, but he never has, he's going to get impatient when you can't spontaneously run off and play when he wants to. This is especially true if you have children and he never has. If he's never been married or lived with a woman, he's never had to deal with what's "expected" of him. He's been only responsible to himself and that comes off as seeming selfish. He's just never had to think about anyone but himself.

3. Interests And Activities
If your younger man is still in the party mode, going to clubs, drinking until all hours with his buddies, or is obsessed with things like extreme sports, you might have trouble finding things you both enjoy — besides having sex. Don't get me wrong. Sex with a younger man is awesome. But if that's all you've got going, it's not enough to build a relationship on. If you have enough interests in common, then it's healthy to have your own, separate activities. But you have to have shared interests if you want to build something real together.

4. Education
This can make a bigger difference if you're highly educated, and he's still trying to figure out what he wants to do "when he grows up." But if he's smart, seen a bit of life, traveled around the world, enjoys learning new things, has a broad range of interests, then you'll probably be able to enjoy lively conversations. One of the things Stephen has enjoyed is learning from all of the life experiences I've cultivated. It's helped him open his eyes to new ways of thinking, caused him to develop new interests and helped him see the world through a wider lens.

5. Perspective On Life
What I mean by perspective is how each person sees the world and how open to new ways of thinking a person is. This is impacted by the culture you grow up in, what religion you were brought up in, how your spirituality has evolved, your political leanings, how compassion you are, what kind of music and movies you enjoy, how much money your family had and how they spent it. Basically, all those things that impact how you think about, respond to and take in life.

I'm a big believer in thinking young to stay young. I love to laugh and giggle. I love guy movies and slapstick. I'm fascinated by cultures. Stephen and I giggle all the time and really "get" each other's wacky sense of humor. And I've enjoyed being exposed to black culture through him, which is definitely different than what I, as a white woman, have experienced.