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Hope you're having a brilliant day. First things first, I've been reading your blog for a few years now and you've changed my life for the better, so thank you. Now to the question: I'm a 23-year-old bisexual college student who will soon be graduating and moving to the other side of the world. When I was in high school, I had this one teacher who I always thought was super hot. He happens to have an equally hot wife. We've kept in touch and catch up every now and again. We had a few drinks the other night and I got the sense that maybe the attraction is mutual. Would it be too weird to proposition them? I can't help but think it's now or never.

Needs Official Wisdom

You know what, NOW? I am having a pretty brilliant day. It started with some fruit and yogurt, then I banged out next week's "Savage Love" in one of my favorite cafes, then I went to the gym. (Gotta take my antidepressants.) Later I'm going to grab an early dinner with a friend and then we're gonna check out a Keith Haring exhibit and then we're gonna go do something I can't share here—but if we ever meet in person, NOW, ask me and I'll tell you all about it.

As for your question... it brought to mind an episode of Broad City that I liked a whole lot more than tanvi rajvanshi did. Suffice to say, NOW, if you do decide to go through with this—if you hit on your old high school teacher and his wife—here's hoping it goes better and/or isn't as creepy as that time Abbi Abrams (Abbi Jacobson) hooked up with Richard Miller (Mike Birbiglia), her old high school English teacher.

As for your specific question: Would it be too weird to proposition your old high school teacher and his wife? Which is just another way of asking, Should you proposition them?

I'm not going to tell you what you should do. But I will say this: All propositions are weird when you think about it, aren't they? Also: you only live once, what do you have to lose, the one thing people on their deathbeds regret more than the passes they made that were shot down (so mortifying!) are the passes they didn't make that might not have been shot down (so [whatever the German word is for regret over a sexual encounter that didn't happen but could've goes here]!).

But don't listen to me. I frequently get yelled at for encouraging people to go for it—in a respectful way, of course, after inviting the other person(s) to say no if the answer is no and, if you're a man making a pass at a woman, after pausing to consider the different ways men and women are socialized and the very real possibility that you could be making a pass in such a way that a woman might fear saying no.

So, yeah. I'm going to step off and throw your question to the hive-mind conscience of the SLLTOD: our commenters. Should NOW hit on—in person or via text—her old high school teacher and his wife? I've already tipped my hand. What say you?

It goes without saying, of course, that your old high school teacher absolutely, positively shouldn't sleep with you, NOW.

Listen to my podcast, the Savage Lovecast, at www.savagelovecast.com.

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