My boyfriend and I started dating three months ago and we established some boundaries in our relationship. I told him I would feel uncomfortable with him keeping contact with women he flirted with in the past (or, in reverse). I asked him how he would feel about this if it was me and we both agreed that we didn’t want that happening in our relationship. He went through his following and deleted all contact with women he had something with. We still had a few instances of me finding out he actually didn’t took all of them out. He fixed it and told me he really forgot and I forgave him but I also told him sincerely that every time I found out there was actually something else I felt like that was a low blow to our confidence. He assured me he was being completely honest this time and I wouldn’t find anything else. Fast forward to yesterday, I found out he actually had flirted with his current girl best friend many times (in the past). The problem with this is that he told me he was 100% platonic with her because he knows her for a long time. I was completely okay with their friendship because I trusted him. Yesterday, I also saw (in his presence) that he sent her photos of his body (no genitals, and also, in the past, before we started dating).
Also, he traveled for two weeks and there were text messages of him asking her when he could see her. He actually went to her house but told me a different story, in which the girl’s aunts invited him. He sent me pictures and everything and the family reunion he told me about happened but he was planning to see her before this even happened and he didn’t told me anything.
He tried to tell me I really wouldn’t find anything else if I give him one more chance but I genuinely don’t know if we can come back from this.
TL;DR: Finding out my boyfriend wasn’t actually platonic with his girl best friend and I’m considering breaking up with him.