Should I go on a date with this guy?

aural914
So there's this guy that has been "flirting" with me on social media for some time now - we went to highschool together but were never really friends. I saw him out at the bar a few times I said hi to him but he didn't offer to buy me a drink or ask me for my number. he's a little antisocial and I think he's insecure. He doesn't ask me out directly, he just puts on Facebook or Twitter when he goes out, expecting me to be there. Should I go?
Should I go on a date with this guy?
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