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Should I (a girl) make a move on the guy I like??

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Background to the situation (seriously shortened version- it's actually a lot more complicated):
Basically, a while back a guy found out I thought he was attractive (through a friend of mine). He had a girlfriend at the time so nothing happened.
Fast forward a bit and he's broken up with his girlfriend and I notice him staring at me a lot. We make eye contact or he looks away once I catch him doing so.
We start talking a bit and he's really nice to me, which according to people is rare for him because he's considered to be a huge dick.
Basically, he could like me (I haven't really explained everything that's gone down- that would take about 10 paragraphs) but he's not going to do anything about it because, to put it simply; he's popular and I'm not really up there in his league.
Should I bother even trying anything? Maybe like just asking if he wants to get some coffee sometime or something? I don't know what to do here.

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