When we took our kids to look at colleges, we may have had some similar thoughts, but we let them figure out what was best for them, and they did just fine. One of my s’s is quieter and more shy, but you would be surprised (well probably not) how they blossom in college. My shy one went to a school where all four classes were housed together (of course his roommate was also a freshman when he was) and my more outgoing son was in an all freshman dorm (he turned down the honors dorm b/c he wanted the “true freshman experience“!). Although I am neither a recent Vassar grad nor a male, I can say that sports was not an issue and between gatherings in the parlors/living rooms, clubs, etc, friendships were found and made. I know there are events for the incoming freshmen/women but I cannot recall what they currently are.
**eta just answered above!