Pillow Talk with Diana: “Is He Insecure About His Sex Skills?”

Q: I met a guy about six months ago, we hit it off and after a few weeks we started hooking up. At first we couldn’t keep our hands off each other, making out every chance we got and having sleepovers every weekend. The sex was amazing, but I never orgasmed. I still really enjoyed being with him, it just wouldn’t happen for us no matter what he did or how hard he tried. This went on for about a month and a half and then he started losing interest in messing around, now we only hook up about once a month. Could it have anything to do with the fact that he couldn’t make me orgasm? And why is that so important to guys? It’s not like he couldn’t make me feel good without that.

A: Oh, the ever-so-popular “wtf happened?” question. Without knowing every background detail of your relationship, I’d say, sure, maybe he’s distancing himself because he’s hung up on the big O. But we all know it can be pretty much anything. Guys fall off the face of the earth every day for every reason imaginable, and in my experience, it’s rarely for the reason we think.

You say you still hook up about once a month–who’s initiating these hookups? Is he still showing the same amount of enthusiasm? And most importantly, have the two of you ever talked about the (non)orgasm issue? I’ve been in your shoes–I’m not super easy to please, and it seems like some guys have trouble understanding that sex can be awesome for us without an orgasm, so I usually tend to mention it in a light-hearted way, either be saying something like “no worries, I’m hard to please, but we’ll get there” or by laughing about it if the dude is the first to make a joke about it.

On the other hand, I feel for him too. If the situation were reversed, wouldn’t you feel a little crappy if you couldn’t give your guy an orgasm for months? Even if he assured you everything was fine and the sex was great? That’s why it’s so important to talk about it—really talk about it, aside from any post-sex reassurances you may have given him.

He’s in the wrong too, if he’s acting distant because of the sex situation and not willing to discuss it–but if you’re still into him and you think the orgasm thing is why he’s lost interest, then maybe it’s time to suck it up and confront the elephant in the room. Don’t do it post or pre hookup, and you don’t even have to ask outright if he’s lost interest because he sucks at sex (kidding!). Just bring up the fact that you’re only hooking up once in a blue moon, and see what he says. If it seems like he’s keeping his mouth shut, then out with it–bring up the unspoken issue and you two will have no choice but to deal with it.

You seem like you’re really sensitive and understanding about it, so just approach it that way when you talk and hopefully he responds in kind. If he doesn’t and can’t talk about it like a mature adult, time to take that monthly hookup session and spend it with someone else. Most issues in the bedroom can be worked on and improved–but only when there’s open, honest, adult communication.

Got a question for Pillow Talk? Email me at pillow.talk.cc@gmail.com and we’ll tackle it next time!

[Image via Sky]