I've been with my boyfriend for over two years. In the beginning, things seemed great. But I was naive. It was my first real relationship. I believed everything he said, and I fell for him fast. Well he's older, and he's been through a divorce where his ex wife cheated and left him. That destroyed him and made him very jaded I guess. So he never took our relationship seriously and I caught him talking to girls multiple, multiple times. He cheated on me physically a couple times, one was long term. The most recent thing was about 6 months ago. We went to his friends house and his friends neighbor was hanging out there. She was nice, kind of manly. (We honestly thought she was a lesbian). But everything was cool, she was fun to hang out with and got along with everyone. So I didn't think twice about it when my bf went next door alone with her so he could see her dog. Well the next few days when he was on the phone and I'd walk in the room, he would freak out and hang up. Then I saw their messages, that they were sending almost naked pics and saying he was going to take her out and then take her home etc. he told her that I was his "friend" that night. So this is one example. I trusted him, didn't follow him around, and look where it got me. I love him to death. I want to marry him & have a family with him & he wants the same. It took him time to trust me & get comfortable with me but not these past few months I can see a huge change in him. I don't think he would cheat again. However, when he drinks, that's when he gets himself in bad situations. One time he went out to the city for the night with his guy friends. Came home, his phone was sitting on the table and I see a text pop up from "Jessica (hard rock cafe)" which is where he just came back from. He's very friendly, so he told me that his shy friend liked this girl so he got her number for him.  Yet she was texting my boyfriend...it's always an excuse. With the girl I mentioned before, the neighbor, he told me that it was a set up because he just wanted to see if I was looking through his phone. There are many other stories that I won't go into. But this is why I'm still very reluctant to put all my trust in him. We talked about it and he said when all those things happened, he was in a different frame of mind. He didn't know if he wanted to be with me, he thought id end up leaving him for someone else so he tried to make himself seem like an asshole so that I'd leave him.  Now we are in a different place, and I do trust him more because I can see a change in him. Plus I live with him and he lets me see his messages straight from his computer, so there not much he can hide anymore. But the question is..he wants to go back out to the city this weekend without me, since it's another "guys" night. I want to trust that things are different and that nothing will happen, but I can't help but feel uneasy about it. He said how will I ever trust him if I don't give him the chance to prove himself? Which I understand. But I'm so used to trusting and letting my guard down, just to get hurt. I'm stuck. I don't want to tell him no you can't go. (Even though he said if I don't feel comfortable with it then that's fine, he won't go). But I don't want to be controlling. I don't want to have to give him a curfew, have him call me every hour, have him take videos of what he's doing with the time showing. He said he'll do that no problem, because he knows he has to make a lot up to me. But I know what he's capable of. I know he can lie. I know that there's a chance he can walk off with his friend, talk to some girls, go to their hotel room, and he'll be drinking so who knows what can happen. I know I can't be in this relationship if it'll be like this forever. It's not fair to ether of us. He's being patient with me, and I don't want to seem controlling. But I feel like if I give him some "orders" like just to check in with me every now and then, etc, then bets the only thing that'll help me start to trust again. It scares me so badly because I'm banking on our future together. I want to be with him. So knowing that one drunken decision can ruin it all, terrifies me. Again, I know he's changed and I hope he really means it. I know I have to give him a little leash if I want to trust him again and let him prove himself. I just know I'm going to have such bad anxiety that night when he's out. Sorry this is so long and I'm rambling! Does anyone have any advice or experience and can help me to feel better about this, or how he and I can work on this more healthily? Other than breaking up.  Thanks!