u/paradoxicalduck

I apologize for the long post ahead.

I’m 30M and my boyfriend 23M and I have been together for a few months. I love him deeply, and there are many things I genuinely love about our relationship. We communicate openly about sex, watch porn together, share fantasies, and generally feel very comfortable with each other.

I was cheated on in my previous relationship, so I know I have some anxiety and trust issues. I tend to overthink when my boyfriend is distant or when I discover something I didn’t know about.
Recently, though, I’ve learned several things that have made me question whether my anxiety is the only problem.

Before we became official, my boyfriend had an FWB relationship with a guy, “Win,” who has a long-term girlfriend. They had sex as recently as March, while my boyfriend knew Winnie was in a relationship. My boyfriend now says he was selfish and did it purely for physical pleasure, and that he no longer holds those values. He says he wants to become a better person.

Win also lives in my boyfriend’s house and has repeatedly made unwanted advances toward him. They’ve had a sexual history, and even after we became official, my boyfriend sometimes shared a bed with him despite knowing Winnie could make advances. My boyfriend says he rejected the advances and didn’t consent to the touching. Most recently, Winnie touched him inappropriately. My boyfriend didn’t tell me immediately because he was afraid involving his family would create a huge conflict. Eventually, he confronted Winnie and clearly told him to stop. Winnie repeatedly said “okay” and “it’s your life.”

There was also an incident where my boyfriend installed an app known for random video/live encounters. He said he downloaded it because his libido spiked and he intended to go live, but stopped himself and didn’t actually do it. We had previously agreed that one-on-one sexual lives with strangers would cross a boundary for me. He felt guilty and apologized.

I’ve also recently learned that in previous relationships, even while exclusive, he would sometimes respond to people who clearly wanted to get to know him romantically, although he says he would pull away once conversations became intimate. He says he doesn’t do this anymore now that we’re together.

Most recently, I discovered that he messaged a sexual content creator after finding an account the creator had posted. He says he was excited that he found the account himself and wanted to show the creator for “clout,” and that he wasn’t trying to flirt. What triggered me was that he didn’t tell me about the interaction. I immediately started thinking, “What if the guy responds and it turns into something else?”

The confusing part is that I’m actually very open sexually. We watch porn and masturbate together, and I genuinely enjoy seeing my boyfriend attracted to other people. I’m considering whether I’d actually be comfortable with him flirting or having sexual interactions with other people if we were completely transparent about it, but I haven’t discussed this with him yet.

At the same time, loyalty is extremely important to me. I don’t want to change my boundaries just because I’m afraid he’ll feel restricted or leave.

My boyfriend has also shown me a lot of love and vulnerability. He wrote me a heartfelt letter for my birthday, has given me meaningful gifts, reassures me constantly, admits his mistakes, and says he wants to become a better person. I don’t think he’s a horrible person, and I don’t want his past to define him. I genuinely believe people can change.

But my trust is currently waning, and my anxiety has actually gotten worse. Sometimes when we’re apart I get chest tightness and difficulty breathing because I worry about what might be happening, although I know some of that is probably my own anxiety and past betrayal.
So I’m conflicted.

Am I being naive by staying and believing he can change? Are these genuine red flags and signs that we have incompatible values, or am I judging someone too heavily for his past while he’s actively trying to change? And how would you approach rebuilding trust in this situation?