Sleeping with friends is risky, even if you're both into it. Because, no matter how many times you say you don't want to screw up your friendship by sleeping together, you usually do. And, lucky you, since it usually doesn't pan out as a sexual relationship, you get two for the price of one — a screwed-up relationship and a screwed-up friendship. If you're lucky, over time, the weirdness subsides and you can re-establish some semblance of friendship, but it's never the same after you've seen them naked.
Still, the temptation is understandable. When a guy and a gal get along really well, unless one of you is gay, at some point, you wonder whether it might work as a relationship. You've got the compatibility thing down, all you have to do is throw some nooky in there and you've got the makings of a fabulous relationship, right?
I get a lot of letters from people who suddenly find themselves feeling more than friendly toward a friend but aren't sure if they should do anything about it.
But venturing into that territory can be awkward and perilous. Because you know that if you bring it up and your friend thinks it's the stupidest thing he's ever heard, things will get weird. He'll distance himself to avoid giving any wrong signals and you'll feel stupid and awkward.
On the other hand, once you start thinking of your friend that way, you'll probably feel awkward and weird around him anyway, so you might as well clear the air so you can get on with either a relationship or the friendship.
The key here is to not make it look like you've been pining away for this person since you met them. That'll freak him out. Bring it up casually. In a particular chummy moment, when you're getting along real well, mention that you love how the two of you get along, that you wish you could have this kind of friendship in a relationship. Gauge his reaction.
If your friend gets weird on you, he knows where you're going and doesn't want to go there. If he seems open, ask him if he's ever thought about you as anything more than a friend. Then flip him a casual, "Just wondered, because sometimes, I can't help think that since we get along so well, whether we might work as a relationship. But I never let myself go there because the last thing I want to do is ruin our friendship." This way you're being honest, but not heavy. It's more conversational.
By not making it a big deal and more of a random thought, you'll minimize the discomfort if your friend has never thought of you that way. And while they might get a little weird, your friendship should be able to recover.
If he has thought of you that way, you've gently opened the possibility.
Have you ever successfully gone from friends to lovers?
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