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August 27

How do I have sex with him without hurting his feelings?

Filed under: Advice — posted by Breakup Girl @ 9:35 am

Feels like the first time on November 2, 1998

Dear Breakup Girl,

Ok, I hate asking for advice. About anything. I detest asking for directions when I’m driving (I get lost a lot) and I really, really, really hate asking advice about anything personal. But, jeez, I’m confused. No, wait, nervous is more like it. Here’s the deal: I have a boyfriend. I love him a lot. We have a good relationship. He’s totally sweet, I’ve known him since I was a freshman (I’m 18 now and in college) and he was a sophomore in high school. In fact, we once dated [three years ago] too. So our relationship has a pretty strong base. I’m completely secure and happy. Great. Super. Wonderful. Right? Problem is, we recently agreed to start having sex. Now this is not a “should we or shouldn’t we” are we ready kind of question. I know I’m ready. I’m not a virgin, haven’t been for a while, and I’m comfortable with that. It’s not like I’ve been sleeping around. I lost my virginity two and a half years ago to my best friend…it was a mutual curiosity thing, and I’m glad I lost it to someone I love as much as him…even in a friendly way. I’ve been with two other guys since (both long-term relationships) and haven’t felt guilty or weird at all. Until now. Cuz, see, the thing is, well, he (my boyfriend) is a virgin. Yep, 19 years old, never slept with anybody. Don’t get me wrong, I love that. I think it’s totally cute. It makes him even more attractive. I just feel kinda strange having quite a bit more experience than him. He knows he won’t be my first, we have an honest relationship. And I can tell it’s weird for him. I know he still really cares for me and all, but I think it’s like, painful for him to think about other me with other guys. In fact, he told me so. How do I put him at ease? I love the guy, and I feel so loved and flattered that he would sleep with me. I know he’s turned down lots of other girls, so for him to feel ready to sleep with me, only me, really says a lot for his feelings. He’s a really sensitive guy (almost scarily femininely sensitive) and I want him to know that it is equally special for me, which it is. So it basically boils down to this: How do I have sex with him without hurting his feelings? Strange question, I know, but I’m worried! Thanks a bunch…

— Nicole

Dear Nicole,

Tell him: “Pooky, I know this experience mismatch might be a little weird for you, and I wouldn’t blame you if it were. You might have wanted us to be each other’s first, together, but yeah, that’s kind of out of the question at this point. And I feel kinda strange about it, too. But here’s the thing: I love you, and I feel so loved and flattered that you would choose to sleep with me. I know you’ve turned down lots of other girls, so for you to feel ready to sleep with me, only me, really says a lot for your feelings. I want you to know that it is equally special , in its own way, for me. It is. I promise. I hope that you will believe me and that I will continue to do everything I can to show you how true that is. But if you want extra proof, get this: you know how I HATE to ask for directions, never mind advice, especially personal stuff? Well, I’ve been so concerned about your being comfortable that I actually wrote to Breakup Girl for some insight on how to handle this. You want firsts? Well, that’s one for me. So. You wanna get the light?

Breakup Girl


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