Love Letters

My friend wants to lose his virginity — with me

Our families are also close, so this won’t be just an uncomplicated summer fling.

Submit your questions for Meredith here.

Q. ’m in college and have been friends with this guy for a really long time (our families are good friends, so technically we’ve known each other since we were born). We’ve always gotten along really well, but we also have this weird sexual tension. Our parents probably assume we’ve been having sex since we were in high school.

In reality, we have never even kissed — until now. Recently on a family trip, the topic of sex came up (we can discuss a wide range of topics without it being weird). He’s never had sex, but I have.


We started talking about having sex, mainly so he could lose his virginity, but also so we could enjoy the experience before I return to college.

Having sex with him would mean a lot to me, but I fear it wouldn’t mean anything to him. He has said things such as: “If we really wanted to have sex, we would have by now,” and “Deep down, I know we probably shouldn’t.” When he kissed me for the first time this summer, he said part of him wanted to “just to see if it would be weird.”

In my heart I want to have sex with him, but in my head I don’t think it’s a good idea. What should I do? — Weird

A. I want to tell you to follow your heart and have a glorious end-of-summer romp, but I can’t — because it will most likely lead to heartache.

You need to tell this man that your feelings for him are complicated and beyond friendship, at this point. Even if you don’t want to be his serious girlfriend, you love and care about him. He’s going to be in your life forever. If this is just something for him to try, and you’re simply the most convenient candidate, it’s not a good idea.


You should explain that if and when the two of you do have sex, you want it to mean something — and to know that he really wants it. You don’t want to feel like an experiment or a cure for boredom. What the two of you have is so much more.

Also, you’ll need to be sure that you’re both ready to navigate whatever happens after this kind of intimacy. It sounds like you can’t just disappear on each other. Think (and talk) about what it might feel like to be together and then go back to the way you were. Because at this point in your lives, that’s what will happen. — MEREDITH


Always listen to your brain. That heart does stupid crap all the time. MCDIMMERSON

“You need to tell this man that your feelings for him are complicated and beyond friendship . . .” Mere . . . Merebear . . . this is exactly how you make every future joint family trip awkward. Just. Let. Things. Lie. Have fun being flirty friends and don’t bring up the sex thing again.


In Mere’s world, there’s nothing that can’t be improved by talking it to death. ROADRUNNER

You want it. He doesn’t. Neither of you would enjoy it. LUCILLEVANPELT

Sex changes a relationship forever. You can’t go back to holding hands. Be prepared. ASH


Meredith Goldstein’s novel “Chemistry Lessons” is now available.