<human>: Could you distill the essence of the text into 1-3 sentences?

Basically I had a huge crush on my dorm RA from last year and as such I was never able to actually date her (especially since I also ended up working in housing). Now she is no longer my RA but lives in another area of town and we are trying to find time to hang out again.

Now there were a few times where I could tell there was something between us last year but neither of us wanted to persue anything since neither of us wanted her to lose her job and have to drop out of school but since things are different I really want to try and show her how much I care about her.

Thing is I have no idea how to actually start a relationship since every girl I've been with in the last year had been either short term or just fuckbuddies to distract me from her. 

A female friend of mine told me that next time I invite her over to walk with me and my dog that I should just hold her hand to see if anything goes from there and that it would be "cute". To me it sounds just incredibly awkward to do to someone but I don't know. What should I do?
<bot>: Really like my RA from last year. Want to ask her out now that I have a chance. How do I go about this without being awkward as fuck