Sex with a Best Friend

Q: I'm 26 years old and a virgin. I've never had a girlfriend and never even kissed a girl. I've pinpointed the reason for this to be that I was a fairly ugly guy until a few months ago when I had an operation to fix my overbite. Now I feel as though I look okay. My best friend is a woman and I told her I wanted her to be my first, not because she's just an easy option but because of who she is and what she means to me. I told her that I've always wanted my first time to be with someone truly special where I can look back with no regrets. She was flattered but she had a bad experience in the past where she had sex with a friend and afterwards he didn't want to be her friend anymore because it wasn't going to lead anywhere. So now she's hesitant. She says that it's possible that it can happen. There was a point recently where I wanted to be a couple with her and she said it wouldn't happen but I stayed her friend. I hope that showed her that my friendship is for real, not a ploy just to get in her pants. When she says "it's possible," does she really mean it? Why not just say "thanks, but no thanks, if she doesn't want to? -- Jay

Dr. Susan: Coward. You're hoping for the safe route to experience, and there's no such thing. There's no way your female friend (or you, for that matter) can know what will happen to your relationship after you have sex. The fact that she's so nice and you like her so well might make it hard for you to go back to the former way you were together. It could get messy, especially because you admit you have had feelings of wanting to be a couple with her in the past. You'll build a lot more confidence in yourself if you take on a stranger (after getting to know her!) than if you keep pushing your friend to give herself to you. You might learn some of the "how" of sex, but a lot would be missing if she just did it out of charity. And anyway, you've never even kissed a girl. I know a couple of great guys who began their intimate life as late as you are. There's no shame in it. Get out there and meet women. Someone will click, now that you're ready. And consider this: What if you had sex with your friend, and then you fell in love with someone else who was insanely jealous of your friend because you've been intimate with her? As to why she doesn't come right out and say no, she sounds like the type who can't say no outright but has to do it very gently, just as she has already done. Take it as a NO and move on.

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