Q: In college my friend and I made out for a bottle of vodka. Desperate times calls for desperate measures, am I right? Anyway, ever since then I’ve had these really vivid daydreams about it anytime we go out for drinks. It’s been years, but goddamn do I ever want to jump my friend’s bones. Maybe it’s because she’s kept her perfect figure while I have fluffed up to a size eight muffin-topped hybrid of my former self and my mother. Or maybe it’s because I really am bisexual and she kind of awakened the proverbial phoenix from its ashy slumber. Whatever the case, I kind of want to ask her out on a girl’s night that ends up with her sleeping over and having sex with me. Am I completely insane? Should I just curb my urge by sleeping with another girl and not fuck up our relationship?
A: Don’t, I repeat, DO NOT DO IT! If nothing has transpired between the two of you for years, that’s your answer. And if a bottle of vodka was involved, it’s likely your friend is more lush than lez. Even if by some fluke chance she went for it, the next day would be the most awkward morning after of your sexual career. Every time I’ve slept with another straight girlfriend, we wind up drifting apart and never speaking again. Regardless of gender, sex is sex and the aftermath is typically complicated. You’ve crossed a line and now no matter what happens you will both find it hard to bounce back to the relationship you had prior. For you, that might be fine. But for your friend, she may no longer feel comfortable being as close, talking about boys and even changing clothes while you’re in the room. This is obviously worst-case scenario, and if she did pull any of this shit I’d have to think she was a homophobic prude with no real strength of character, but do you really wanna risk finding this out? It’s not worth it. Go out and find her lesbian doppelganger and fuck her brains out. Everybody wins.
Jenny Mollen is a writer, actress and all-around gorgeous sassy badass who lives in L.A. with her dog Teets and husband Jason Biggs. She writes about her life on TheSmokingJacket.com in her highly popular column What She Said. Follow her on Twitter at @JennyAndTeets and on Instagram at JennyAndTeets2.