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Good stuff, Jayer! Always enjoyed reading your stuff.

What kind of advice exactly are you looking for? I'm not feeling the sweater. It looks like the shoulders sag and the sleeves look a tad short. It also seems too long, but I can't really tell. Overall the idea is not bad, but the shirt kills it - I would definitely close some more buttons...

I don't think leaving the ball in her park like that is your best bet. Sure, it may work, but do you really want to be that guy who spends his time anxiously awaiting a phone call he might never get? If she's giving IOIs like you say she is, just put a smile on your face, get in there, make her...