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#WhatTheHellHappened: To The Woman Who Wanted to F**k Her Old, Engaged Gym Teacher

For this week’s #WhatTheHellHappened we caught up with “Anonymous,” who originally wrote us for advice, because she was ACHING to sleep with her long time crush and former high school teacher! “Anonymous” had recently reconnected with the guy, and they started sexting and talking about hooking up IRL. The problem? The teacher was already engaged to another woman. And in a shocking turn of events, my mom and I agreed! We both thought that sleeping with the teacher would be a terrible idea. In response to “Anonymous” mentioning that the teacher said that he was only engaged out of obligation, and because he and his fiance had a mortgage together, my mom artfully noted, “Earth to teacher’s pet, he is not engaged to his fiancé because of a mortgage. HE IS ENGAGED, BECAUSE HE WANTS TO MARRY HER. Wake up and smell your common-sense killing hormones! You are the side piece…” I agreed with that sentiment, and added, “I never think knowingly being the other woman is a good look (ovaries before brovaries), but let’s put that aside for a second. If you were just going into this affair with the intention of scratching a ten-year-old itch and knocking something wild and sexy off your bucket list, I could at least understand that…But from what you’ve written us, it sounds like you’re going into it with the idea that you genuinely want to be with this person. Think about it; let’s say you break them up and the two of you start having steamy, locker room, fantasy sex and then even start dating…what’s to stop him from cheating on you a few months down the line? How can you ever trust someone who cheated on his fiancé with you?”

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

“I’ve had a massive crush on one of my old high school teachers since he started working there … I left seven and a half years ago and recently got in touch with him. We were texting for a few days, then grabbed a coffee together and just talked about general stuff and filled each other in on our lives. In the texts before the coffee, we flirted a lot, but coffee was just casual and then it went dead for a week. Then we started talking again and this time things got really intimate over messaging. We’ve exchanged ‘pictures’ because this is just a bit of fun, and we’ve even talked about meeting up to follow through with our intimate conversations. My issue is, he’s engaged. He’s with her because of the whole “mortgage commitment, etc,” but he doesn’t ever have anything nice to say about her, so I’m wondering whether to go through with it and try and get him to see that he shouldn’t be with her, or if I should just walk away. I’ve never been THAT girl to get involved with an unavailable guy, but I’ve been crushing on him for 10 years, and now I’m starting to develop feelings for him. It would be amazing if I could get some advice! x” -Anonymous

So, #WhatTheHellHappened to her?

“So… as you know I was torn between what I thought I was feeling and following through with a kinky fantasy I’d had for a very long time about my teacher.

Well…? Back in January we did meet up for a drink, and we ended up going back to my place and we slept together. Though it was wrong on so many levels it felt sooooo right – even when I realised it wasn’t because of any feelings I had, it was just excitement and very good sex.

Fast forward to now, we still keep in touch, he is still engaged, we have talked about meeting again but we don’t actually get round to it because we’re both so busy..but there are no romantic feelings on my behalf and I’m pretty sure there are none on his other than wanting to have a bit of fun – I do feel awful about what we did behind his fiancés back.. but did I mention it was really good sex??

Lots of love!” – Anonymous

@CrazyJewishMom:  Well, I feel for the guy’s fiance – that marriage is going to be tough! Maybe skip the next meetup and find another guy.

@KateFriedmanSiegel: Yeah, I agree. As I said in the original advice column, it’s ultimately the fiancé’s job to not cheat on his partner, not yours. That said, it still sucks to be cheated on, and it sounds like you recognize that and feel bad about your part in it. I’d just say, this old teacher is objectively not the only ‘really good sex’ in town, so for everyone’s sake, it’s probably a good idea to avoid hooking up again. Nonetheless, I am glad to hear for your sake that you’re keeping it light and not expecting him to leave this woman for you – as my mom and I previously wrote, that’s probably not realistic, so if you are going to continue, try not to get invested for your own sanity.


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