Should we have sex or not?

I'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 (I probably consider him one of my best friends), but we've also always had 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 before – until now. Recently we were on a family trip and the topic of sex came up (we're very open with each other and can discuss a wide range of topics without it being weird). He's never had sex, but I have.

Essentially, we started talking about the idea that we should have sex, mainly so he could lose his virginity, but also so we could enjoy the experience for a bit before I return to my university. But ... should we have sex or not?

I think that deep down, I know that having sex with him would mean a lot to me, and my fear is that it wouldn't mean anything to him. It doesn't help that he has said a number of conflicting 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, as we discussed this, 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

I want to tell you to follow your heart and to have a glorious end-of-summer sex romp, but it does sound like it might lead to some 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 him and care about him. He's going to be in your life forever. If this is just something for him to do – to get an experience over with – and you're simply the most convenient candidate who can help him, 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

Readers? Is the experience worth the possible heartache?