So it's the time of the year when I have girl frustrations. I mostly just need to type this out, because it forces me to actually think it all out.
In this case, I met someone about 6 months ago now, and I had an inkling that she was interested in me. Just a couple examples: over the summer, our mutual friend passed along an invitation to come to some soiree happening at her place that he said explicitly came from her, and more recently she has asked me to move to sit near her in our one shared class (it's a seminar so unfortunately there are few chances to get a word or two in edge-wise). While it sounds kinda clear-cut while I'm typing it, this attention doesn't seem to be too terribly consistent or anything, which makes me think it's for a different reason which I'll get to. A combination of being busy and too shy has stopped me from wanting to try anything until around about now.
The problem I'm having is that a few of my features, namely being extremely soft-spoken and having very sensitive, weepy eyes, makes it seem to most acquaintances that I am extremely sad all of the time. I'm actually quite happy to just wake up everyday, and this contrast is something that many of my close friends have commented upon. Needless to say, I am constantly surrounded by a lot of unnecessary but rather thoughtful sympathy, and I'm worried that I'm misreading her potential interest/concern here. I would enjoy making a move and having it turn out alright, but I know that historically I've been wrong more often than right.
I have been thinking about inviting her out to a few of the more interesting bars around the area, since she just recently hit 21. The issue I have here is I don't know if I should straight up say something like "Hey, let's just you and me try a date at this cool bar I've heard!" or something closer to "Hey, there's a bar that involves lots of chalkboards and free chalk to draw with, let's go sometime!"