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Originally Posted by Miss Modular
Cosmo's right. He's in the city, I'm stuck in a college town several hours north.
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Well take the Metro North down to the city and meet up! After all, you need a place to crash... But if you're not so bold, I would suggest being progressively more and more flirty and get a feel for his feelings.
But if you insist on the letter route, I'd make it as chill and non dramatic as you can. Writing a serious letter is like dropping a bomb - can make the other person feel awkward and uncomfortable, not to mention surprised, and from my own experience that has not worked out well.