If you really don’t think you’re ever going to trust him, then he’s not the guy for you. Imagine if you’re married and you don’t trust your husband 😳 — or if you have children with him and you don’t trust the father of your children! 🙁 This isn’t a good situation for the future.
I’m not sure why you’ve been off and on for five years, but at a certain age, it’s time to decide what you want in a man and a relationship and you have to be honest with yourself about whether or not he’s the person who can give you the kind of relationship you want — or if you’re wasting your time (and his).
If you do break up with him, whatever happens during those break ups, is none of either of your business. So if he dated during a break up with you, that’s not your business — it’s his. It’s not cheating, so let it go. Same goes in the reverse. And if you don’t like his friends, rather than force him to drop them (good luck with that! 🙄 ) you should consider that this is part of who he is and decide if he’s really someone you want to be with. Getting to know his family and friends is a very good way to get to know who HE is. You can’t choose your family, but you can choose your friends and if he chooses people you don’t like, then maybe he’s not right for you.
Let me know if this helps or not.
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