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Ask Mom & Spawn: Sleep With My Teacher Or Stay With My Boyfriend?


“Hi! So, I’m returning to my high school in a teaching role soon, and the teacher I’ve always had an intellectual (sapiosexual here) attraction to is my mentor. He’s friends with my dad, and they play golf together regularly, and he’s always been kind of around as I sorted out college and a career and such. Problem is he’s significantly older (18 years), and I’m currently in a 2.5 year long relationship with a guy I 70% see myself marrying. We have issues, particularly in the academic arena (I graduated from a top college; he has a GED and is very insecure about the comparison), but we genuinely could get married without issue. Said former teacher has made innocuous commentary about going to musicals together (current boyfriend is not so into the theatre, whereas I was a theater kid in high school and love it), and I have a huge desire to take him up on the offer. But I can’t reconcile cheating and won’t break up with my boyfriend just to chase an old-but-not-even-a-bit-dead dream… help needed!” – Anonymous

@CrazyJewishMom:  Rip off his spectacles and throw him down on the teacher’s lounge table!

@KateFriedmanSiegel:  Uh, no. Don’t cheat on your boyfriend.

@CrazyJewishMom:  Oh, come on! She’s with the guy 2.5 years, and she’s not even sure she wants to marry him? It’s break up time! You obviously know the boyfriend isn’t a keeper. MOVE ON. Preferably ONTO teach’s manmeat! I did something like that in college, and it was a whole lot of fun.

@KateFriedmanSiegel:  Gross. To me, it seems like there are two issues here that you should VERY much separate in your brain. 1. Your feelings about your boyfriend. 2. Exploring a relationship with your (former) teacher turned colleauge. And you ABSOLUTELY need to figure out what you want to do about the first question before you even consider the second.

@CrazyJewishMom:  What’s the question? The boyfriend’s insecure and doesn’t share her interests! It’s time to load this guy onto the dump truck and move on!

@KateFriedmanSiegel: Obviously, we do not have enough insight into your current relationship to tell you what to do there but, again, you really need to make sure you’re not sabotaging a perfectly happy, substantive relationship just so you can fulfill a silly teenage fantasy. That said, if you ultimately decide to break up with the guy and want to explore something with your teacher, I have a few thoughts. First, that is a big age gap.

@CrazyJewishMom:  Oh please! Age is just a number!

@KateFriedmanSiegel: Yes, but with something as substantial as 18 years, the two of you are at very different stages of your life. Do you want kids? Would he? Important to think about if you want more than just a fling with this guy. Another BIG concern is the dad connection. That has the potential to be incredibly awkward and even friendship ruining!

@CrazyJewishMom:  Follow your dreams. But find out if the old guy plays for the other team. After all, he loves musicals.


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