I got this article from a seedy website. I would link to it, but there are pretty much naked people all over and I don’t want to advertise porn. But I think it actually has some valuable advice for those trying to stage a hook up with their best friends. The advice holds somewhat true for straight and lesbian couples as well, but as the article was target for gay men, I left in the pronouns.
There’s something about best friends. You love them, you share everything with them, but you don’t really want to have hot gay sex. Except maybe once. We’re only human. We’re not made of stone. Emotions can have a habit of over-spilling. And this is one occasion when it’s arguable great first time sex with a ‘new’ partner can happen while quite drunk.
These are the rules:
1. Right now, never mind tomorrow morning or earlier this evening, do you both want to have sex? Or is it just you? Or is it just him? If either of the latter two options applies, stick to the beers until neither of you is any longer capable – You can just drool on to each other about love, like straight friends. If, on the other hand, you really are both up for it, then it could be time for some fun.
2. Do you or does he have a boyfriend? To whom are you or he committed? If there is a one-on-one boyfriend in the background, bear in mind that if you do have sex now you won’t be seeing each other again for about six months – and then it will be boyfriend-chaperoned and distinctly frosty.
3. Do either of you really want a relationship with the other person – and being best friends has been the second best alternative to that? If so, it could be sex will shake it out of your system, or it could be Fatal Attraction time. Up to you.
4. Are you very good at keeping sex and love conceptually separate? Sex and friendship can coexist perfectly well, but if you associate sex with intimate love and commitment you are heading for trouble.
5. Are you going to learn something about your best friend you’d rather you didn’t know? In terms of ‘kink’ and performative preferences, it could be best to have lots of talk about sex beforehand. Like you haven’t.
6. To sum up: will sex be great fun and a way of sharing friendship and bonding, or is it a very big deal? If the latter, press ‘play’ on the next DVD.
7. And finally: Don’t fondle your friend in the morning. That was last night; this is now.
Keep in mind hooking up with your best friend, can be the start of the best relationship of your life or the end of one of the best relationships in your life. But in most cases it will fall in between. Good luck in life and love.