I (f30) have been with my boyfriend (m31) for 5 years now and we are in that phase in our relationship where things are getting more serious. When I met him, he had a frat-boy mentality and still does at times. He was obsessed with his college days and thought life was just one big party. He had issues with alcohol, lust, & quite honestly was not a good boyfriend at the time. When we made our relationship official, he had a trip already planned to South America with 2 of his buddies.

We just happened to bump into a girl at a bar that was from exactly where he was going. He asked her for her information (with my consent) and I was under the impression that she would give him travel recommendations via text. He told me that she was going to have her family show them around town, which I was ok with. Days before he was about to leave, I decided to help him pack and found some women’s shoes. I was confused by this and confronted him about it. He said he met that girl we had bumped into in a parking lot because she wanted to give the shoes to her mom. He said he did this out of good favor because she was helping him out. I let it go and trusted him.

When he was on the trip, I hardly heard from him. He blamed it on having no reception but I could still see his Snapchat stories. In one of the stories, he posted him and the boys going up a mountain in a chair lift and each guy had a beautiful woman beside them. I was extremely upset but waited for him to get back to confront him.

He told me he didn’t think they were good looking and they were just showing the guys around town. I chose to try to move past it but I was angry and uncertain. A few weeks later he butt dialed me while drunk out of his mind and he was talking with some friends about these “Beautiful women” in South America. Followed by saying “I got one”. His friend chimed in “you mean your gf, right?”. To which he drunkingly said yes to.

Fast forward to current times, I developed major trust issues and a habit of snooping through his phone. To which I found out that he actually met up with the “shoe-girl” and initially invited her over to his house but they agreed to meet at a bar instead. She set up all of the guys with one of her friends to show them around. After a ton of arguments and threatening to breakup, I found out that one of his friends cheated with one of the girls but him and his single buddy allegedly did not hook up with anybody. The worst that he said happened was that he danced with a girl.

Anyways, he has also showed disloyalty by meeting up with his ex fling in the beginning of our relationship without my knowledge. They apparently met up at a bar about 4x and at one time went to her house. He thought he got rid of the evidence but I found out about it through another device. I found out about this after 3 years into the relationship despite it happening during the beginning of the relationship. I broke up with him and he begged me to hear him out. He reached out to the girl and she told me nothing happened between them, so I tried to make it work.

Over the years, I have gotten resentful and feel like I cannot move past the lies because I don’t know if I know the full truth. He has changed a lot since we first started dating. He doesn’t act like life’s a big party, he has tried to go to therapy, and he seems more respectful. The truth is, I know he is still capable of hiding things and he can be vengeful when upset, which scares me. I’ve tried breaking it off but my Anxious-Attachment and his persuasiveness makes it very difficult at times (I’m in therapy for this).

Since then, he calls me when on these trips and will talk with me. I asked him not to go out clubbing or to strip clubs & to share his location (for safety purposes too) and he agreed. During his most recent trip, he called me to see if I could look up recommendations for things that could do that night. I found a jazz club a few blocks down and thought it might be cool for them to do. About an hour later, I decided to check his location to see if he made it to the jazz club and see he’s at a strip club on the same street with the boys. I call him and he said he didn’t know and tried to manipulate me by saying I sent him there and set him up.

I also found a picture of a girl that follows him on IG (not his type) with some random guys and him. He looked hammered and I’m not sure but by speculation, it looked like they were at a club. After snooping some more on her IG, I see she was traveling with 2 other girls that were his type. I don’t like that he party’s in other countries. I don’t think it’s appropriate and it doesn’t make me feel safe.

Also, these motorcycle trips can be dangerous. The guys go to remote areas during some parts and have run into issues. One guy almost died from 2 different accidents. A bike broke down in a remote area and they had to hitchhike it back. The also got robbed by police for not wearing seatbelts (cop threatened them to either pay off or get sent to jail).

I feel that the older we get, the riskier these trips are. Not to mention, that he uses up a majority of his vacation time on these trips and can hardly go on a trip with me. Last year, I booked my own international trip and told him I was going with or without him. He decided to go with me and didn’t go on the boys trip.

This year, he’s been talking about the trip with the boys again. Truthfully, I’m tired of it and feel like it’s too much worrying and stress whenever he goes. Plus, while we’re working towards rebuilding trust, I feel like it could cause more harm than good in the relationship. So anyways, the other day, I snapped and told him it was either me or these trips. He was taken back by the ultimatum and feels stuck between the 2. AITA for making him choose?

Summary:

My boyfriend (31m) of 5 years hid hanging out with girls behind my back. Twice around/during an international boys motorcycle trip & another time his ex fling during beginning of the relationship. I feel that he’s matured since then and have been working to rebuild trust. These trips can be very dangerous and I don’t feel comfortable him going on them anymore. He’s planning another trip this year. AITA for making him choose either me or these trips?