Navigating the Choppy Waters of Past Hookups and Present Partnerships: A Reddit Love(?) Triangle

Well, well, well, if it isn’t the old ‘should I have told my partner about that one-time hookup with my bestie from way back when?’ conundrum. Grab your popcorn, dear readers, because this is a real story from a real person on Reddit, and it’s a juicy one. Our protagonist, let’s call her ‘Ms. Caught-In-The-Middle,’ is stuck between her beau, ‘Alex,’ who’s got a no-history policy, and her BFF, ‘Chris,’ who just happens to be a blast from her sexual past. Drama ensues, and guess who’s here to dissect it all for you? That’s right, your favorite sassy commentator, Roger, at your service.

Imagine this: two years of blissful ignorance (or is it?), and then bam! Out of the blue, Alex inquires if Chris and our girl had ever done the deed. Why now, Alex, why now? Was it a sudden attack of jealousy, or perhaps an intuition gone wild? Whatever it was, it led to our protagonist spilling the beans about a drunken night from their high school days.

Now, before you jump to conclusions, remember that our protagonist was under the impression that her past was a no-go zone, thanks to Alex’s ‘hear no evil, see no evil’ approach to relationship history. But, oops, it turns out there was a footnote to that agreement she might have missed. Cue the relationship turmoil and an ultimatum that leaves her choosing between her boyfriend’s comfort and her friendship with Chris.

Here’s where it gets stickier than a movie theater floor on free popcorn day: Alex decides he wants nothing to do with Chris and demands our protagonist to follow suit. Fair? I think not. But who am I to judge? (Just kidding, judging is literally my job).

Now, let’s not overlook the fact that this love – or rather, friendship – triangle seems to have been built on a foundation of communication as sturdy as a house of cards. Our protagonist argues that the hookup was a meaningless blip in the timeline, not worth mentioning, while Alex seems to disagree. And so, dear readers, we’re left with a love story entangled with a past fling and the glaring issue of trust and boundaries.

**Roger’s Hot Take:** Darling, let me lay it out for you. In the grand scheme of things, honesty, especially about past romantic entanglements that have morphed into present-day friendships, is not just a courtesy; it’s a necessity. Yes, Alex initially opted out of the history lesson, but relationships evolve, and so do their rules.

However, issuing ultimatums and cutting off ties isn’t the way to nurture trust and understanding. Both Alex and our protagonist need to navigate this sea of past hookups with open communication, a dash of empathy, and, frankly, a good therapist wouldn’t hurt either. And as for you, dear protagonist, maybe next time, consider that some secrets are too heavy to keep, even if they’re from a drunken rendezvous that happened in what feels like another lifetime.

So am I the asshole? Oh, darling, that’s the wrong question. The right question is, how can we grow from this? And my advice? Grow together, or grow apart. But whatever you do, grow. There’s your hot take, served with a side of sass and a wink from yours truly, Roger.

Original story

Hi THT! Weekly listener, first time poster. Sorry as this one may be a little long but context is important. 

I (25f) have been dating my partner (25m – let’s call him Alex) for two years this July. From day one, Alex has had zero interest in hearing about my history – sexual, relationships, etc. He asked me specifically not to bring up any history with any partners as it makes him uncomfortable. No talking about history with ex’s, no talking about sexual experiences, no talking about past dates, etc. I happily obliged as I understood. I told him I don’t mind hearing about his history as long as I am not compared to anyone in his past. He agreed. We then also both agreed that we would never allow one-on-one time with people we’ve had history with out of respect for one another.

A year into our relationship, we ran into someone I had sexual history with at a party and after a very mature conversation, we revised the rule to be that I let him know if I have history with someone if he happens to meet them. I said sure and that was the end of the conversation, very mature and blunt. 

My best friend (25m, we’ll call him Chris) has been in my life for 13 years. We are tight knit – we don’t hang out as much as we used to as he now lives 45 minutes from me, but we find time to reconnect every now and then. We talk pretty much bi-weekly. Each time we’ve hung out in person, Alex has been there. Alex and Chris are friends and get along well and have spent a decent amount of time together. Alex has known him pretty much as long as he’s known me. 

Me and Chris had a drunk hookup in high school (over 8 years ago) after I had gotten out of a 5 year relationship and was super lost and lonely. We both realized it was a mistake and that was the end of it, we moved on and not a single thing changed romantically between us two. Since we are both very much in each others lives, we are very transparent with our partners of our history as to not cause drama. He tells all his girlfriends and once they meet me, they realize I’m no threat and we get along so well. Same goes for any guy I’ve dated – except I never told Alex as our initial agreement was that he didn’t want to hear about my history. 

Here’s where I’m confused if I am the asshole or not. Earlier today, Alex had randomly asked me if me and Chris ever hooked up. I told him yes, in high school. He asked if it was sex, and I said yes but it was once and never happened again because we both realized it was a mistake. He had said that makes sense, but was upset and wondered why I never was truthful with him sooner since he’s known Chris for a while now. 

I reminded Alex that in the beginning (when he met Chris), he had asked me not to bring up my history with previous people. Alex then reminded me that we revised the agreement – to only tell him about partners if he had to meet them – and that I should’ve mentioned Chris on that day since he had already known him for a year at that point. I had told Alex that Chris didn’t even cross my mind as a part of that list because that one time was so long ago and so unimportant in my eyes. It genuinely did not even pop into my mind as history. He said he understood, but is now giving me the cold shoulder and saying that per our agreement, I’m not to hang out with Chris alone anymore and he wants absolutely nothing to do with him. 

I told Alex in the past that me and Chris have never acted weird about our history – nor do his partners/my partners and I expect the same of him. Alex is being adamant that he’s not going to ever be around Chris ever again and that I need to do the same. I told him “No, Chris is my bestfriend and the time’s I’m around him, you’ve also been there. So you need to pick between me spending time alone with Chris, or you being around when Chris is around.” 

I’m so conflicted as I GENUINELY have absolutely zero romantic connection to Chris, even when we did hook up (nearly a decade ago) it was solely a one night stand. No romantic connections on either end at all. I don’t know where to go from here. I love Alex dearly and we hardly have relationship problems – this being our like second argument

So THT, am I the asshole?

EDIT: bc holy crap some people canโ€™t read. I had said he UNDERSTOOD why I didnโ€™t bring it up sooner. He understood meaning he saw the reasoning for me not bringing it up. Heโ€™s not mad at that. The argument weโ€™re having is around time spent with Chris – wether Alex wants to just deal with it and also be present or not. I ask that you please review the post before replying and understand that heโ€™s not mad at me for hiding it – weโ€™re arguing because of he doesnโ€™t want me to spend one-on-one time with Chris, yet he doesnโ€™t want to be around him either

EDIT 2: update is posted in the comments. I tried posting it in the subreddit but it got removed