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My boyfriend is 24 and I am 19, and we have been dating for 10 months. A while back I found out that he had hooked up with a 40-something year old woman when he was 21, in a “friends with benefits” type situation. They never dated, and I’m not sure how long this went on but it ended when she moved to Ohio (my boyfriend and I live in Pennsylvania). He said that they never dated, neither person was cheating on anyone else, and it was a purely physical relationship.

It’s not the fact that my boyfriend had this relationship that bothers me. What bothers me is that he doesn’t think it was a mistake, he doesn’t regret it, and doesn’t think there is anything creepy about the age difference when it comes to who you sleep with. He does have a rule in the age gap for people he dates, but not with whom he sleeps with unless they are much younger than him.

He keeps trying to understand why I think it is creepy, but I can’t explain why because it just seems self-evident, especially when you consider that the woman’s child was older than him. And that she slept with someone younger than her own child. It just really bothers me that my boyfriend doesn’t find that weird.

My boyfriend thinks that the reason I care about it is because I feel inferior to that woman since she is much older and would have more sexual experience than I do (I was a virgin when I met my boyfriend), but I don’t really feel like that’s what my problem is.

I don’t know what my problem is actually, and that’s my question. Is it reasonable that I would find this creepy? If not, why do I find it creepy? Is there another way I can think about it so I can get over this feeling?

Zoe

Once upon a time I had a male client who was very judgmental when he found out that his girlfriend participated in a threesome with two men. While he loved the idea that she was sexually adventurous, he couldn’t get the image of fingercuffs out of his head. I pointed out to him that he had seen a number of prostitutes, and that, if we were to be objective, his behavior can only be seen as equally questionable.

I just think that you — like most of us — are judgmental of things that you can’t understand, haven’t experienced, or wouldn’t want to experience.

He hemmed and hawed and tried to justify it, but he couldn’t wrap himself around his own hypocrisy. He held the deep-seated belief that men can do what they want, but if women do what they want, they’re slutty. The real truth is that we should all be entitled to our secrets. Presuming he’s clean, he shouldn’t tell her about the hookers, and if she knows that men can’t handle the image of their girlfriend being double-teamed, she should probably keep that one to herself.

The real issue here, Zoe, isn’t your boyfriend’s FWB relationship with an older woman. Hell, that’s a fantasy for most guys. It’s really about your feelings about it and what you’re making it mean.

But you already knew that. You said that you don’t even know what your own problem is, as if I’m going to be able to tell you. I can’t. I’ve heard some crazy shit on this blog over 7 years and your boyfriend’s cougar affair is nowhere near the top of the list. I just think that you — like most of us — are judgmental of things that you can’t understand, haven’t experienced, or wouldn’t want to experience.

Nowhere is this more apparent than in the realm of sex.

Don’t worry, Plushies and Pony Players, we’re cool.

I find it hard not to be a little judgmental of people who participate in alternative sex acts. When my wife and I went to the Museum of Sex in New York, there was an exhibit on kink, and we were shocked to find out just how vanilla we were, in the grand scheme of things. But, like any prejudiced belief, it’s intellectually easy to overcome. Just because I don’t want to do something doesn’t mean someone else can’t take pleasure out of it. And if no one is getting hurt, far be it from me to deprive someone of his/her kinky sexual enjoyment.

You’re just really confused because of two reasons: a) you’re young and extremely inexperienced, and b) you would never sleep with a man twenty years older.

You’re just really confused because of two reasons: a) you’re young and extremely inexperienced, and b) you would never sleep with a man twenty years older. Because your loving boyfriend did, you’re experiencing some cognitive dissonance. But I’m telling you — as a guy who once had sex with a woman 15 years older, it is certainly not creepy, deviant, or reflective of his ability to be a great partner. Stop judging your boyfriend for having more experience and finding older women attractive and you’ll be fine.

And, one day, believe it or not, you’re going to learn that 40 isn’t very old at all.