Okay, so I (22F) started dating my current boyfriend (25M) about a year ago and it's been going great so far except for one thing that happened when we went out with his friends a little while ago that I haven't been able to stop thinking about.
His 2 friends (both guys around his age) kept making jokes about my boyfriend "being a pedophile" and "only wanting to date really young girls" and then started going into details about his sex life before I had met him including that he had slept with one of his friends from high school previously as well as making jokes with them about incest (not going into details about why I didn't find that funny, but he definitely knows this). This made me really uncomfortable which he knew but he didn't ask them to stop or anything, and when we got back to his house I just wasn't in a good mood at all (Also because I had baked him something the day before and he threw it away after not eating any of it saying that he doesn't like deserts when I've seen him eat them before, but this isn't really relevant.).
Anyway, moving on, since then I've noticed he's still REALLY close with his friend that he's previously had sex with. I always knew he was pretty close with her because she comes up in conversation, and he had told me that he slept with a friend from high school, but I had no idea they were the same person until his friends told me. He told me that they're just really good friends and that he's known her since high school and the only reason he slept with her is because they were both drunk at the time.
Despite this, and maybe this is just me being insecure since this is my first relationship, I feel like he must've liked her at least a little bit to have sex with her at the time (I said this to him one time and he got angry/annoyed at me for it so I try not to bring it up) and he has since ignored me multiple times when I'm talking to him on dates/when we're together because he was texting her. I trust my boyfriend, especially since both him and this girl are dating other people now and she doesn't live in the same state as us, but I don't appreciate things like being ignored in a restaurant because he's texting some girl he's previously slept with.
Long story short, my boyfriend is a great guy, but his friends tend to try to make me uncomfortable by bringing up his previous sexual activity and he still seems strangely close with a "friend" from high school that he's previously had sex with.