Search Results: dating sister''s friend

So there's this girl who I don't know particularly well, but has always been friendly and sweet to me. She is going to be staying in the area close to me for the foreseeable future, because she is going to Optometry school. I don't know that I want to date this girl, but here is the situation that makes me wonder if this is a good idea.

I met the girl, X, in college, as a part of a group I met by extension of some of my high school friends. X was always very sweet to me, and I always have a good time at the parties she went to. I didn't really care for the rest of the group. There were a few people I liked, but I didn't have anything in common with them, and their parties were usually not enjoyable to me. The ONLY parties I enjoyed were the ones that X went to. I never really had contact with X outside of that scene.

Well as time has gone on, the people I had nothing in common with don't want to chill with me. They like me, and we have a group chat, but I'm not really "one of the guys." The little contact I had with the other girls has died with time. These relationships are mostly positive (only two ended on a bad note), but they just aren't particularly close. X has a sister who dated one of my HS buddies, and since breaking up got weird about being in touch with me (the guy she was dating was weird about her talking with other guys...).

I reached out to the group chat, to ask the guys if they wanted to chill when I was in the area that X lives (it's nearby a city that a lot of us are living), and I got a... frankly insulting response. X even reached out to me on FB to get a critique on her letter for school... so she does respect me, and that letter showed me that we do have some common ground.

X and I never really had much contact in college, but the contact we had was great... I don't really have a way to naturally get closer to her, and I expect that our mutual contacts would be weird about me trying to go through them. Should I even bother?