Search Results: breaking up relationship

This is a long story but;
My best friend is a serial dater, which I'm not mad about. As long as he's being safe I support him.
That said after 1 week of dating someone new they always want to meet me because as my friend says "I talk about you a lot so they want to get to know you." To which I say, thats nice but it's been a week, shouldn't they get to know YOU first?
Regardless I try to be a good friend and meet them anyway because I know he wants my opinion.
The real problem comes in when my friend inevitably gets bored or finds some fault with this man no longer than 2-3 months into dating him.
At that point since we did the whole try to get along because your dating my friend thing, almost every time he breaks up with someone, I get harassed by the hearts he's breaking.
I no longer accept friend requests on any platform from the guys he's dating but despite that they still try to message me asking about my friends feelings.
I will readily admit only about 50% of the time do I believe my friend has a legit reason for ending the relationship, so it does make him an asshole and I get them wanting answers more than "it's just not working out"
My question is am I a bad friend for asking that he dates them at least a month before involving me? Is there a better time frame? Or is this a hopeless cause regardless of timing because my friend is great in so many ways but dating isn't one of them?

Have you ever been in a position where you were (or are) in a relationship and had an opportunity to cheat but didn't go through with it? The options given are usually when the opportunity between you and someone else happens, but regarding the final option: there are couples where if they are breaking up, one person might tell the other to go be with someone to finally end up and be done with them, or people battling illnesses who can no longer have sex give their blessing for their partner to have sex with someone else.

If you've ever been in these situations, how did you handle it, and did you partner ever know about it?

So my boyfriend has been my best friend for 5 years. In high school we dated for about 2 years. Then we broke up for 2 years. Now we've been dating for almost a year again. Best friends through it all, and friends with benefits for a while.

But I just found out I'm high school he cheated on me for a few months before breaking up with me. And he then basically dated the girl for that summer when we were broken up. They were just talking, hanging out, and kissing on the cheek. This girl became my friend once we broke up and was like the main one I leaned on and who supported me through the break up, me never knowing. I suspected he was with another girl but he would never tell me who. After all this time I just found out this month, and we talked through it and everything. I can forgive them, but I don't know if I can get over it and forget it. It sucks bc this relationship we've had now has been amazing, much better than when we were young and dumb, we've been really happy and healthy. I don't want to give that up for something that happened a long time ago, but I can't trust him now (i already have trust issues from childhood trauma!) And i don't want to be that toxic girlfriend who always goes through his phone, i hate that. But that's how I found out, because I suspected it still and it still hurt not knowing and he let me go through his phone so I found out. But since he lied to me for so long it just makes me sick to think it barely affects him now and he never would've told me. Also back then, they broke it off bc he never stopped loving me and realized he never liked her like that he'd just think of me, and he broke his heart talking to other guys. So I don't know. What would you do in my situation?