Should I (Seriously) Date A Guy Who Is 10 Years Younger Than Me?

We say we love each other. We are close friends. But is the age difference too much?

Jun 3, 2013 at 2:00pm | Leave a comment

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Do you know what one of my favorite movies is? "When Harry Met Sally."

Do you know what one of the most unlikely real-life romantic scenarios ever shown is in the movies? That's right. "When Harry Met Sally."

Do you know what the dating situation I currently face in my life is like? Exactly.

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Could I pull off a May-December relationship? What about a May-mid-August relationship?

I have a good friend who is about a decade younger than I am. We first slept together in 2011 right after I ended a relationship with someone who was two decades my senior. And we have slept together several times since then.

So what's the problem?

Well, the age difference for one. When I am 50, he will be 40. When I am 60, he will be -- OK, fine, you can do math, I suppose. I have several friends who have been able to make these May-December romances work out (does this qualify as a May-December even? maybe May-August?), but the realist in me thinks that it might be doomed. Here are a few typical evenings we've spent together.

Typical Evening 1: We go to the dog park and watch my dog run around and make jokes about everything and everyone. There is a lot of sexual tension and sometimes we even make note of it. Neither of us are trying to date one another so it's kind of like that really rich chocolate cake that you might smell but not actually partake of.

Typical Evening 2: We end up hanging out at his place. We watch videos, catch up on each other's lives, and sometimes the tension is so much that we act on it, and it's fun and delightful and we feel great.

Typical Evening 3: We end up hanging out at his place. We watch videos, catch up on each other's lives, and sometimes the tension is so much that we act on it, and suddenly it's too real and it's not fun and it's not delightful and we don't feel great.

Typical Evening 4: We give each other dating advice, reading through streams of texts and exchanges and OKCupid messages that each one of us have received and analyzing what this and that means.

Typical Evening 5: I have set him up with one of my younger girlfriends because I am realistic and he goes out with one of them, and they both enjoy it, but then nothing really serious happens. Pretty soon the two of us are kissing once again.

Typical Evening 6: We discuss going to Vegas to get married.

Typical Evening 7: We approximate the chances that we could actually have a real relationship.

Typical Evening 8: We decide that we definitely should not date.

Typical Evening 9: We are in bed together.

Typical Evening 10: We say how glad we are to have each other as friends and that we can be so honest about everything and not have to worry that our friendship will be ruined by dating.

Having read all this over, it seems clear to me that we should date. We have all the same interests, the same sense of humor and there is a common bond of understanding and love.

And yet.

I don't think I would ever want to lose that. Besides, if he really wanted to date me, wouldn't he just say that? Aren't I kind of doing exactly what you're not supposed to do where you turn a friendship into meaning something more? (Or in this case, a friendship with benefits?)

Maybe the real question isn't his age -- but my assertiveness in the situation. Yes, he has begged to see me in the past and demanded that we go on dates and I wasn't interested. But lately, I'm the one bringing up the question of why aren't we dating a lot more than he is. And that's a problem.

I know that women don't have to abide by standard gender roles (he's the driving force; she's meek and submissive) when it comes to dating, but there are also major kernels of truth in "He's Just Not That Into You."

Perhaps I should throw out the rulebook entirely. Forget the age difference. Forget who's pushing what, and just exist within it. When I want to see him, see him. Enjoy our friendship. Be with him romantically if that seems right. Date other people, and if it's meant to happen, it will.

Because no matter what happens, I do love that ours is a connection that has lasted -- and I know will last -- the test of time.

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