Should I act now or just leave it?

A male age 36-40, anonymous writes:

I'm in need of some advice. I broke up with my last girlfriend over 4 months ago and have been single since then. It's been OK, but I've never been that enthusiastic about long-term singledom and feel ready to begin a new relationship. At the moment, there's a girl in my college whom I've developed something of a crush on. We've only spoken a few times but I would like to ask her out. Given that the term ends on Thursday and I basically won't see her again til October, do you think I should act now or just leave it?

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A female reader, Emilysanswers  +, writes (19 April 2009):

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