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Depends on your definition of "cool."
I realize I'm not a girl, but I thought I might be able to contribute a little bit...
Personally, I don't like shirts with writing on them in general, as far as what I find initially attractive. Since you're "entertaining the possibility of trying to maybe pick up a girl," I would assume you're looking for a "first impression" kind of shirt. That said, here is what I find gets the best results:
A button down shirt. Something somewhat classy, but relaxed enough to be comfortable. You want to look nice, but you also need to be relaxed in it. Personally, I go for solid, cool colors: black, dark blue, a deep red (if I'm feeling sassy =P ), or something of the sort.
That's just me, though. Ultimately, what you should wear is something that you feel comfortable in, something that compliments your style. You also probably want to consider where you're going out. If you're going to a dance club, a Hulk shirt PROBABLY wouldn't be the best choice. Similarly, if you're going to a video arcade, I probably wouldn't wear a 3 piece suit.
Oh, and shirts get extra points if the girls think it looks good on you. Chances are they're right. I've learned to accept this fact =P
I hope this was helpful.
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