this is kinda on a tangent (and on a platonic level) but I was buying bread for a canteen the other day and was literally carting around 12 loaves of bread - yes, twelve
This guy in the queue behind me leaned over and joked "Did you just buy up all of Cole's bread?" and then we chatted for a few minutes before the next cashier was free
^ That's supposed to be an example of how easy and non-awkward it can be to talk to someone you don't know very well. You don't *have* talk dive straight into the "hey guess what I like you" - just get to talking level first. If talking about the weather is a bit banal, then pick something else - maybe she has a cool sticker on her backpack that looks like it's got one of your favourite bands on it, maybe cityrail is totally screwed up and you're (conveniently) close enough to her to say "omg this is so stupid! It's going to be ages till I get home at this rate, what about you?" or something like that