I’m a 32-year-old woman who recently went back to college. I attend a local community college in my area. I absolutely love being back in school and I've embraced being a student in all aspects. Recently, I’ve been spending a lot of time with a man much younger than me—he’ll be 21 this month. He’s well traveled, well spoken, polite, sweet, caring, and we have great conversations that go on for hours. Last week, I spent the night at his house. We didn’t have sex, not even a kiss. We slept in the same bed, he wrapped me up in blankets when I got cold, but he never made a move. The next morning, he brought me coffee in bed and we talked for hours until I finally went home. I’m super confused. I like him—even though I know that the chances of this turning into something serious are minimal, and I’m ok with that. But I also don’t want to tell him that I like him and ruin a great friendship if he isn’t interested in me. Is there really a chance that a soon-to-be 21 year old could be interested in a 32-year-old woman?

Please, help me figure this out!t

Back To School

My response after the jump...

Yes, BTS, there are lots of soon-to-be 21 year olds out there who would be interested in 32-year-old women. So go ahead and make a pass at this boy already. He's probably sitting at home wondering why you—older, wiser, and infinitely more experienced you—didn't make a pass at him the night you slept over. Hell, I'd wager that in the time it took you to send me this question, BTS, the boy jacked off about you six or seven times.

Make. The. Pass.

And if I'm wrong—if he's not into you or if he's gay or if he's asexual or if identifies as a self-pollinating flowering shrub or something—here's how you avoid seeing a great friendship ruined: "Really? You're not into me? Wow, I'm sorry. I totally misread your signals—and so did this dumb gay dude I wrote to asking for advice. Jesus Christ, I can't believe i listened to that dumb fag. Anyway, I tell you what: Let's not let this ruin an otherwise great friendship, okay? Things will be awkward for a little bit, sure, but we can power through the awkwardness if we both make an effort. I'm willing to make that effort. Are you?"

He'll either say yes to the pass (90% chance) or yes to making an effort to power through the awkwardness (10% chance). If it's the former, you'll be fucking the guy. If it's the latter, you can stop wasting your time wondering if the guy wants to fuck you. Either way, BTS, you come out ahead.

Finally, BTS, about this: "I know that the chances of this turning into something serious are minimal." I think you're confusing permanency for seriousness. You can have a perfectly serious, perfectly lovely, perfectly rewarding relationship with this guy without it having to last for the rest of your lives. Most relationships fail, BTS, so a fair application of your odds-of-permanency standard would require you not to enter into any romantic relationships at all.

UPDATE: What he said:

Also campsite rules.

And for the soon-to-be-21-year-old boy: The Tea and Sympathy Rule.