This is one of several issues I've been struggling with lately. My best friend has done a lot for me, and honestly, probably going to be a life-long friend (we've already been friends for like 12 years without strangling each other).

But there are also things about him that... honestly, I sort of question how much I could really trust him.

For one, dude is cheating on his wife who's about to have his baby. Call it "blue pill" if you want, I think that's pretty shitty. He's an incessant flirt, and has more than once 'joked' about asking a girl I was interested in, if she had a "private snapchat" (he pays some chicks to see nudes, which is fine, but I thought asking a girl I was into was pretty scummy). I told him not to even ask, but I kind of suspect he did, which would explain why things got awkward between me and said girl out of nowhere...

Long story short; I feel like the guy is a good friend, but I would never feel comfortable introducing him to a girl I was into. And I feel like that's kind of a weird line to have to draw with your best friend.

I'm legitimately curious how you guys would handle similar friend dynamics? Do you just accept it as "that's how some dudes are", or do you think it's a more serious issue where you need to set boundaries, and end the friendship if he isn't willing to respect you?