Should I plan an elaborate sleepover to seduce a friend?

January 19, 2008
I have a friend that is inexperienced in any form of sex whatsoever at age 18. I think that he may be gay but I am not sure. I was thinking that his birthday is a few months away, that maybe I would plan a b-day sleepover of the two of us. My birthday present would be a porno. I figure that way, I could set up an entire situation that results in the best night of his life. Do you think that this is a wise idea, or should I just forget it?—Anonymous
If I understand you correctly, you have a friend whose sexual orientation is uncertain. You want to ask him to spend the night, give him a gay porno, and hope he gets so turned on that he hops in bed with you and loses his virginity in utter ecstasy.

It's actually not a bad plan... as long as your friend happens to be gay, finds you to be his type, and wants to have his cherry popped. If he's straight, not interested in you, or would prefer to stay a virgin, your evening may turn into a major disaster that can end a close friendship.

My suggestion? Have the gay porno handy (just in case!), but don't give it to him as a present. Give him a more traditional gift, and spend much of the evening talking to him and getting to know him. If the moment comes up, you may even want to come out to him. In a polite way, that is. Don't do it by putting your hand on his thigh. Who knows? Things may work out the way you planned, in which case you can suddenly produce the gay porn as his "real gift." And if he prefers to stay platonic friends, you have both grown closer for the experience without jeopardizing the friendship.—Aaron Lawrence

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