I don't want to run the same old "But he's different!" script but I am feeling pretty stuck about this. Potential guy and I have been friends for over a year. Since we've met, he's always treated me with the utmost respect and has never acted untoward in any way since we started dating. He's polite and has a genuine appreciation for his mother who raised them as a single mom. He has also been really involved with my interests and has offered to show up to my events unprompted despite the fact that it's really not his usual scene. I was stunned the moment I realized that he's called me smart more than good looking in the time we've known each other. He has a good relationship track record of only a few long-term relationships which ended amicably.

Game night with the boys came up and they needed extra players so he asked if I wanted to join in. I didn't mind and I was linked in to the voice server. Most of his friends are from his old school's basketball team since he is a college-level athlete. They're the kind of dudebro-y jock type that I just can't deal with on a good day. The banter was mostly harmless and whenever things got a little uncomfortable he was quick to get them in line. The guys were generally nice but I definitely wouldn't want any of my friends dating any of them.

I know the kind of friends a guy has are DEFINITELY telling of something about him but I'm unsure what exactly it says about him. I try to reason that his upbringing is more similar to mine than it is to his friends and that may make a difference. Most of those guys are from the big city and have all of daddy's money to keep them afloat. He and I come from neighboring small towns from the other side of the country with just enough to get by. Maybe I'm being a little too optimistic about him? He's pretty simple minded with a good nature so a lot of things do go over his head. Am I overestimating him? Am I underestimating him? I'll take anything.

tl;dr : I don't want to touch "the boys" with a 10-foot pole. What does that say about the boy?