All names are fake.

I (48M) have been dating my girlfriend Kelly (50F) for nearly two years. We are currently on vacation with her son Ryan (23M) and his girlfriend Emily (23F), as well as my sister, BIL, niece, and her boyfriend.

To preface this, I know Ryan very well. I’ve known him for nearly a decade now, I was his coach in high school and we grew very, very close. He is practically a son to me. He’s also been dating Emily since high school.

When we were planning this trip Kelly said that Ryan wasn’t allowed to share a room with Emily. I thought she was joking, but she was not. I know Ryan is sexually active, and I’ve known by word of his mouth since he was a teenager. I said fine, and the technical plans were that Ryan and my niece’s boyfriend would share a room, and my niece and Emily would share a room. Obviously that room arrangement wasn’t going to last.

Everyone was fine with the technical room arrangement, the girls even had a “slumber party” one of the first nights. Ryan picked up that this was just to appease Kelly. I handed him his keys and said “give the second one to whoever” and he immediately gave it to Emily. My niece did the same in giving her spare key to her boyfriend. This is exactly what everyone thought would happen.

Anyway, somehow Ryan had left his wallet in our room last night. Instead of bringing it to him at breakfast or knocking on his door or even shooting him a text, Kelly used the key in it to walk into his room. She saw things she didn’t want to see.

To be fair, they weren’t having sex. What was described to me was that they were both nude, covered up at least on their bottom halves, but they were snuggled up and he was running his fingers on her back. This sounds like how most loving couples are after having sex.

She was in hysterics. She refused to come to breakfast. I told her that was fine but she wasn’t going to make this a big deal on our vacation. Emily very sweetly apologized to me and said she knows how Kelly can be, which frankly made me feel terrible.

When I went to retrieve Kelly from the room she was still in a mood. She expressed to me how upset she was and I told her be thankful all she saw was the snuggling and not the actual act. That made her really upset, and I told her she was overreacting. Ryan is an adult who has been with the same woman for years. She has confided in me before that she doesn’t like Emily, but frankly I’ve never seen her do anything wrong. She’s a bit punky and Ryan is a bit more preppy, but she’s a sweet person who cares deeply for Ryan and vice versa.

She called me every name in the book when I told her she was overreacting. She called him a child and accused me of taking Emily’s side over her. I’m genuinely concerned. I’ve even considered the possibility that she forgot to bring some mood regulating medication because I have never seen her act like this, and I’m being shunned by her for being an asshole. Currently we’re all sitting on the beach while Kelly mopes inside.

ETA: I wanted to add some relevant information that I see asked in the comments. So Ryan and Emily live together and have for I want to say five years. Ryan paid for his and Emily’s portion of this trip. When Kelly brought up them not sharing a room as I was booking it, I thought she was joking and just laughed. It wasn’t until we were checking in and I was passing out keycards that she reminded me of what she said, and at that point, instead of arguing about it in the lobby, I said fine and handed people their keys and told them to do whatever they want, I just wanted a drink and eat some fruit on the beach.

She is in therapy and is aware of her unhealthy attachment to her son. She does take medication(s?) for mood regulation, however I’m not sure if she currently has them.

I think that’s all for now, if I see anything else I will add it. I’m sorry I can’t get to all of the comments; there’s a lot of them, and I’m on vacation!

I posted an update here.