Ask Mom & Spawn!

#WhatTheHellHappened: To The Woman Who Wanted to Sleep With Her Old Teacher … But Also Had a Boyfriend

For this week’s #WhatTheHellHappened, we caught up with “Anonymous,” who originally wrote us because she really wanted to sleep with her former teacher-turned-colleague. Problem? Well, “Anonymous” had a boyfriend. Oh, and her teacher-crush was also really good friends with her DAD. In spite of my mom’s usual mantra about workplace romance, “don’t get your meat, where you get your bread and butter,” this time, she thought “Anonymous” should, “rip off his spectacles, and throw him down on the teacher’s lounge table!” I did NOT. But, we did both agree that “Anonymous” was clearly conflicted about her feelings for her boyfriend, and I thought she needed to figure out that situation before even thinking about anything else.

So, #WhatTheHellHappened? Here’s a refresher on “Anonymous’s’” original story, and an update from her below!

“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

So, #WhatTheHellHappened to her?

“Hi Kate,

Sorry for the delay on this one—I’ve been back and forth on filling in the gaps. I still work at the school I mentioned, and I think things could be a little messy if anyone ever put together the pieces. So vague is probably my best friend here.

So where to start… I am no longer with the boyfriend, our educational differences being amongst the underlying reasons we split up. Honestly, the more we dove into the bigger life perspectives and opinions, the more it was a relationship destined for turmoil and an ultimate break up. But that’s probably not the stuff you or your readers want to hear about (although y’all, if you’re doubting your relationship for the real, big reasons—not just because he loves onions and you hate them or some astrological shit or whatever—it’s worth listening to and exploring, not just hoping it will all work itself out.)

First thing’s first: I have not slept with the former-teacher-turned-colleague. But at this point we have made out, and there has been at least some level of nudity. Let me tell you, ladies, the chemistry is so real. And then, he decided to move at lightning speed: wanted me to vacation with him, wanted me to meet his whole family, wanted me to overlook all of the objectively weird situational stuff that’s very much at the forefront of my mind (all of this notably less than a month after any of the physical stuff transpired): I absolutely freaked, but only internally. I am reticent at best about relationships and always have been, so as we stand right now, I’m holding him at arm’s length and doing what I can to not lead him, on while keeping a professionalism at the forefront and continuing to try to figure things out. Short version: things are a shit storm, but I do have wine so things are going to be just fine.

Thanks! And I appreciate your discretion here; what a complicated web I’ve woven…”

@CrazyJewishMom: Good! I’m glad you dumped the boyfriend. You were obviously not in love with him. Guess you should have listened to my spawn about the teacher sex, though.

@KateFriedmanSiegel: YIKES. I’m sorry it’s so stressful! And yeah, I don’t know what came over my mom on this one, but it’s a good lesson: don’t hook up with coworkers!

@CrazyJewishMom: Yeah, that is a good general rule, but listen, you’ll be fine! You’ve got a good job, and this guy will get over it. Just keep him at a distance, and you’ll both move on. And hey, now you’ll never wonder what your fantasy teacher’s manmeat looks like!


Want more advice from @CrazyJewishMom & Spawn? Listen to our podcast here, and tune in every week Sunday at 5 PM ET on the @AskMomAndSpawn Instagram page for our live advice/ podcast recording sessions! We might just answer your question live!

You can also submit your questions below for the advice column! AND follow us:

@AskMomAndSpawn on Instagram, Twitter, and Facebook!

Your Name (required)

Your Email (required)


Your Message


By making this submission, I hereby acknowledge that I have read, understand, and agree to all the terms and conditions set forth herein.

For qualified advice, please visit this website for resources.

If you are a victim of domestic violence, please visit this website for resources or call 1-800-799-7233.


The Latest

To Top