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Got you beat on the IM thing...

Sinbad_EV
I was so nervouse to ask my current girlfriend to be my girlfriend, when we were on our first date and she didn't seem to realize it was a date; I started IMing her across the table we were both sitting at and basically did the whole explaining that "I really liked her and wanted to get to know her better" thing while crouched behind my laptop screen so she couldn't see me... though in retrospect it is very lame to specifically ask a person to be ones girlfrind when one is 20, be it over IM or not... meh.

Responses:
Strong Bad
Yes, yes, and both of you having networked laptop computers on a date isn't lame.

On your second date, did you move up to infrared file-sharing, or was that too hot-and-heavy for you?

Average rating: 4.55

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