I'm almost on break for the holidays, but at the beginning of school starting up again I'm considering trying to ask out a girl for the first time! >< But I don't know if it's worth the risk or not to even try... She's a freshman and went to high school with one of my roommates, and I thought she was pretty adorable from the first day when she was helping us move in. She's hung out in our room a few times and is feeling a lot more at home on campus thanks to me and my roommates. She's so sweet and says things like we're all like a little family and thanks us for letting her join us in our special space to be a part of it. I don't have a full-blown crush on her, but I think that besides being cute, she's the sweetest, most considerate person I've met in a REALLY long time. I also learned for a fact later that she's bisexual and has had a girlfriend before!! Buuuut we haven't hung out that much even though we're definitely friends (I can text her myself without using my roommate as a middle-person), she's a freshman and I'm a senior, plus if she's such good friends with my one roommates, if I DID ask her out, no matter the outcome, I would hate to make things awkward for everyone She probably wouldn't want to try going out with me, and so much can change because of our years in school. I kind of want to say, screw it! and just try because it's my senior year and I've never gone on a proper date even though I'm out at my college, and there aren't very many more opportunities for me to date so easily once I leave campus (college kids dating don't have to worry about transportation or money nearly as much). But I can see so many things being an issue because I worry about these things way too much. Should I at least try? Or should I forget about it?
I think you should definitely try. This is similar to how i asked my first girlfriend out. We were friends but had never really properly hung out. I knew she was bi, that's the only reason I had the guts to ask her out. And if you're already friends it's easier to remain friends if the relationship ends, as i remain friends with my first love, and there's no awkwardness at all.