We've actually had more than a dozen conversations about this kind of thing. He knows that his insecurity and the constant reassurance is an issue. After we talk about it, he usually improves and doesn't get crazy worried or anything. But not long after, he just shifts right back into an insecure person. He has thing with texting me all the time. And while I don't mind him saying "Hi, I'm thinking about you", because I sometimes do it too, sometimes he gets carried away (which we have also talked about a lot) and texts me a lot more. I tell him that I think it's rude to be out with friends and constantly on the phone texting someone, so I don't think he should do it as much. One text is fine if that's what he really wants, but I can't sit there when I'm out with my friends and be texting him. And if I don't text back (even when I'm not out and I'm busy at home with something) he tends to get really really worried and texts me a bunch of things like "ohh...k...well hope everythings ok and you're not mad at me". Just because it didn't text him back within 5 minutes. I don't always have my phone with me, and do not always have opportunities to check it, and this I have explained to him. But like with everything else, it seems like he fixes it and is ok, then after a few weeks or a month he goes right back to doing it.
We actually took a break around a year and a half because I was still having trouble getting over him cheating and his insecurities just added to the stress of dealing with the relationship. So we decided to work on our issues separately so we could have a better relationship together. We got back together (obviously) and were really great at first, and then it just started all back again. We argue a decent amount, and I know that arguing is common and an ok thing in a relationship, I think we butt heads a lot more than we should. We both agree we don't like fighting, but we can't seem to help it I guess. We're very similar, and my mom (she's one of my best friends and I often go to her for advice) has even said that he and I may be too similar to really work out.
Like I said, we've had many talks about issues involving our relationship, so he knows how I feel about certain things. I can honestly say that I'm completely over him cheating on me, and I don't mind at all if he goes out, and he knows this as well. I just don't know if the whole "things slipping back into place" is a sign that the issues will never be resolved or not.
