The next day, he tells his male friend about sleeping with Sally: “Most of the time you go to bed with someone, then she tells you all her stories and you tell her your stories,” he explains. “But with Sally and me, we'd already heard each other's stories.”
I have always thought this line perfectly articulates both the best and worst thing about sleeping with your best friend. On one hand, you don’t have to bother staying up all night discovering everything about each other. You don’t have to exhaust yourself trying to impress them. The heat is off. They’re impressed already. That’s why they’re friends with you. But on the other hand — it’s confusing. There’s no seduction or pillow talk when you have sex with a friend and so it’s hard to know what to do or say afterwards. You can’t really BE sexy. Because there’s no fooling your best mates.
In my experience, if you are close with someone single and of the opposite sex, inevitably there will be a moment when sex is discussed. At one point in your friendship, you’ll stop the car and suddenly find yourselves with an option of turning off into a remote village that you never knew was there. Sometimes you get to that junction out of drunkenness, sometimes out of boredom or loneliness. Sometimes you just find yourself there, very quickly, for no traceable reason at all.
Here’s the first question you want to ask yourself — do you really want to have sex with this person? Or is it because you’re a man and she’s a woman and you can’t be bothered to find anyone else? Is having sex with this person a bit like when you open the fridge and realise there’s nothing in there other than a out-of-date jar of pesto but you eat it anyway? Are you really going to scrape the non-mouldy bit of pesto out and put it on some bread? That also required a mould removal effort? Do you really want to eat this? Or do you think you should just have a cup of tea and go to bed and go shopping in the morning?
Then if you go ahead with it, here are the potential outcomes to prepare for:
1. You decide it was a one-off thing that doesn’t have to be a big deal and your friendship can recover from it.
2. You decide you cannot get over it and it has shifted the gear in your friendship too much to go back to normal.
3. You realise that having sex with them was the most awkward, silent, uncomfortable experience of your life and you wonder why you ever did it. Of course it was going to be like that. You fucked your best mate.
4. You realise that having sex with them was the most bed-breaking, head-board-banging, gorgeous, amazing experience of your life and you wonder why it took you so long to do it. Of course it was going to be like that! You fucked your best mate!
5. You think you can get over it and then you see them with someone else and realise, actually, you can’t.
6. One of you wants to keep sleeping together and the other doesn’t.
7. You wake up, freak out, leave without saying goodbye, go home, pack your bags, take your passport, leave the country and send them a Facebook message five to ten years later explaining that you just felt a bit weird about the whole thing.
8. You both realize you should be having sex all the time. You start dating. You fall in love.
8b. (optional) You buy a house. You buy a dog. You buy some furniture. You get married. You have a baby. You start fighting about the dog and the furniture and the baby. You get divorced. You wish you’d just stayed friends in the first place.
And my final word of warning is a reminder that proper, close, male/female friendships are quite hard to come by. If you've found someone who makes you laugh, who gives good advice, who’ll be there for you at your lowest ebb, I would proceed with caution. That’s a lot to potentially lose on account of an orgasm.
…But then, on the flip side, it’s just sex isn't it? Happens every day. Your neighbours do it. Your parents did it. Every person on the bus has done it. People do it with whipped cream and up bottoms and with five other people and Monica Lewinksy did it with a cigar and Boris Becker did it in a cupboard. It’s just sex. There are entire iPhone apps for people to organise and meet up to do it. It doesn’t have to mean everything. And sure, it could go wrong. But it could also be sort of great. You just have to assess whether the outcome could be good enough to warrant the gamble.
And here I leave you with a quote from Peter McWilliams, who worded this argument in a quip far better than any of mine. “What if it doesn’t work out?” he asked. “Ah, but what if it does.”