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How I did it: Seven drinks, (some really weak) a cute dress, his cute bowtie, taking advantage of the fact that he's so shy and being able to talk his ear off for a few hours at a party. I just finally... DID. I talked to him and we went on our first date the next day. We've been together since and we never fight, rarely have terse conversation, and we appreciate and love each other so much!
Lessons & tips: Stop thinking, put away the pick up lines, and just strike up a conversation about wherever you are.
Resources: Alcohol, a dress from a vacation, and a few friends pushing me in the right direction.