📝 AITA for thinking my boyfriend meeting up with his coworker is cheating

By VastOrnery7179 • Score: 0 • April 10, 2025 3:14 PM


When this event happened...

My boyfriend and I had been together for six months and had a super close bond. I became good friends with his friend group and introduced him to my friends and family. We talked about moving in together and having a child.

When we first met I was very hesitant to date him as we have a significant age difference (he is 54, I'm 34), but he pursued me so steadily that he finally won me over after almost a year of him asking me out. I was the asshole then- I was fresh out of a break up and would hang out with him, make out with him drunkenly, then leave and tell him later when he expressed feelings that I wasn't interested. This happened a couple of times and each time when he texted afterwards I would apologize for drinking too much, tell him I valued his friendship but wasn't interested in pursuing a relationship, and was totally honest about my headspace.

Around Christmas of 2024 I had a major revelation and realized that even though I had kept treating him as a friend and not good enough and too old to date, that I had fallen in love with him. I apologized profusely and was completely honest with him about how I had felt and my discomfort and anxieties about the age gap. Another anxiety I had was that when we first met he had a girlfriend (his own age) who was more of a 'buddy buddy girlfriend' (they didn't live together, went skiing together, rarely had sex, and she was kind of just one of the dudes he hung out with more than anything). Even though he had a girlfriend, he actively pursued me when I was newly single. I ended up becoming uncomfortable enough with the dynamic that I told him he was being totally inappropriate and that I wouldn't be coming around anymore. He and his girlfriend ended up breaking up over it (and fucking rightfully so on her part). About four months later after the dust had settled I started hanging around sometimes but not nearly as often as I had. I always had a lingering discomfort that he was willing to hit on someone actively while being committed to someone else, even if it wasn't the right relationship.

As for the other stuff- me having turned him down (girlfriend or not)- I knew I was going to be climbing an uphill battle having turned him down for a long time, as I knew the power dynamic was skewed in my favor and that he would have to be comfortable and trust me that I was in it, and I did my very best to make him comfortable in every way and show him he didn't need to have doubts about me loving him or that I was going to change my mind. At first he was anxious, but a couple of months later he said he was over it and trusted me completely. I trusted him completely too, and let go of my anxieties about how he had behaved with his ex-girlfriend thinking that it was just because of the nature of their relationship and that shit fucking happens and maybe it isn't perfect.

Us getting together and dating- it was lovely. He acted super kind and wanted to be around all the time. We got along so very well and I was feeling like he was absolutely the right one and that I had been stupid to not see it for so long. After just a month he told me he loved me- which is soon, but as we had known eachother for a long time felt right to me too and I told him I loved him too. We were inseparable. We would go kayaking, skiing, out to lunch, take naps together, make eachother breakfast before work, have stellar sex, and then wake up and do it all again. We did have some conversations that tugged at my anxiety around his level of 'fidelity'- he mentioned that after he first got together with his ex-girlfriend that he had gone out a couple of times for drinks with another woman, but then didn't do anything physical and told his ex-girlfriend. I told him quite clearly that I had no idea why she would tolerate disrespect like that. I said "sure maybe it's not cheating, but the intent is there that you're interested. That's disrespectful." His response is that the ex-girlfriend was 'good' about it, and only asked if anything happened any then moved on. I wondered to myself what the hell he meant by 'good' about it. It was a huge red flag for me that he was characterizing her accepting him stepping out on her as 'good'. But again, I decided that maybe it was just a lukewarm relationship. I rationalized that in my past I had also done things like that, but honestly not since my early twenties when that shit just happens. As an adult, I haven't ever messed around in that way when in a good relationship. In my mind it's just bullshit behavior.

So.. the event!

Multiple parts.

Part 1- he had kept his ex girlfriend around as a friend. I think mostly out of pity- but I set a firm boundary about her coming to friend events as it was mostly couples and it was truly horrifically awkward due to how things had played out with him more or less leaving her for me. So there was our first season of tension and bickering within our relationship. Things were tense.

Part 2- he started acting like an asshole for a couple weeks around that same time. When we fought about the prior subject he said things like "how do you know what she said to blah blah blah was about you"? (Truly stupid Facebook shit), and I basically responded with "quit wasting my time by pretending there isn't an issue". He took every opportunity to deny, deflect, and ignore that a problem existed with her still hanging around, even though his friends all commented on how weird it was and how it was uncomfortable for me.

Part 3- I had a guy who I had been casually seeing before we got together who I had kept as a friend. I was completely transparent about it when he texted and that it was just friendship. I could tell it made my boyfriend jealous anyways, so I never went and hung out with him. One day, and honestly partly driven by feeling disrespected by him arguing about his ex-girlfriend being around and whether it was legitimate (of course it wasn't) and not caring if I hurt my boyfriends feelings, I went and met up with the other guy mid-afternoon in a public place and had a couple of beers. It was just a friendly catch up and nothing weird happened at all. I told my boyfriend I had gone when he came home from work. I ended up even apologizing even though he didn't directly say he was mad because I thought I could tell, and also because I felt guilty, and told him I shouldn't have gone without telling him first and that I wouldn't do something like that again even if I was angry, and that it wasn't right to do whatever I wanted just because I was mad.

Part 4- the dust had settled, or at least I thought so. He agreed to set boundaries with his ex. I apologized for hanging out, even casually, with someone else. A few weeks passed. One night he came over to my house and at the end of the night as we were out drinking on the porch said very casually "I got hit on this week". And I was pretty much like "right on man, how?", thinking it wasn't possibly a threat. And he proceeded to say the following:

"Well my coworker asked me out for a drink, and then when I went she told me she was into me. I told her I had a girlfriend that I loved."

And I was pretty disturbed immediately with him going out with someone I hadn't heard of before (outside of him previously describing her as a real romantic potential a few months before we got together). It seemed like an immediate red flag and not at all ok. I asked him where they went, and he said he went to her hotel room where she was staying in town as she lives in the islands outside of town and was just staying for the night. He described the whole thing incredibly cavalierly, as if he didn't make any choices that he were wrong. And I immediately lost my fucking shit. He said "oh well she needed to let her dog out so we went there" and all sorts of other shit that dismissed the fact that another woman, who he had previously expressed interest in, invited him to her hotel room, and he had chosen to go. More so- he hadn't told me until days afterwards when I'm guessing he decided he better fess up in case I found out some other way. I asked whether he thought in going whether that's what she had in mind, and he said yes and that he thought he would let her down in person. So- yeah, lost my shit. Asked him to leave my place. He was screaming that he had done nothing wrong, I was firm in that even going was completely, and irrevocably wrong and cheating. I asked whether he had told her at work that he had a girlfriend prior to that and if they had been flirting and he said that "it had never come up", then he started talking about how much he liked her and admired her. He put up a front that inisisted I shouldn't be upset, and wouldn't back down. At that point I was crying and screaming and feeling completely shattered. It was like I got punched in the stomach and everything I knew was upside down. I had told him I trusted him completely in the months leading up to that, I had told him that he had my heart.

That weekend I asked him to leave my house. Then I panicked and showed up at his place the next day early in the morning. Then I fell asleep, woke up, howled, lightly punched him in the stomach while sobbing then left. All the while he acted disengaged and aloof, like there was nothing to be mad about. Two days later, I decided to let it go because I didn't want to loose him.

Fast forward two months- I couldn't let it go and would bring it up every month or so in a drunken fight begging for details. More emerged. She had been texting him after they met asking to meet again. He had framed it initially as "she respectfully took the no and said they would be friends and it was a casual conversation just in a hotel room where they sat on separate beds". I began obsessing about it. Nothing added up. He acted distant for two months after the incident. I felt like he was emotionally gone so I held it together during that time, feeling intensely confused and scared and not knowing what was going on.

Fast forward six months further- I couldn't take it anymore. I don't know how I possibly could live with a half story but it was driving me absolutely insane and I thought about it every day. I finally looked at his phone. When she had asked him out over text- it was completely clear that she was hitting on him. It wasn't a request for a casual drink that turned into a come on. The night after he left- she text him a string of "xoxoxo I hope you got home safe". A few days later- "I hope we can get together again" and he says "me too, maybe later this summer!". A few days after that she says "It depends on how bad we want it, I'm easy (with a wink face), I just super like you". He responds, "Aw, probably better there is a body of water between us, because I super like you too". It's clear that they then had an in person discussion where he shut it down. A couple of friendly texts after, but by no means were the ones before a firm shut down.

Over the months I had brought it up he became immediately defensive when I did, yelled, said I was being crazy, and that he had done nothing wrong. Honestly, what bothers me more about this whole thing was my gut feeling for months that something had happened, and that he flatly denied it and pretended like going to meet up with another woman wasn't wrong. It was crazy making at best.

Now- we are totally messed up by the whole thing. I can't let it go, I told him I'd try to let it go but he has never given me a sincere apology. Every time it has come up he gets furious and defensive- to the point where he storms off and now insists I should maybe leave his home when it does come up. He has never been able to just apologize and say things got out of hand, or that it was wrong to meet or text with another woman with that intention.

Ok! All of that to say for the love of god... Am I the asshole? And should I let it go?

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