Man, this is a tough question to answer and i could feel you despair as i was reading. You yourself said that you werent attractive, and unfortunately guys look for that in a girl. Do all the things possible to look attractive, then flirt with him a little and see how he responds. Its all about how he reacts. There isnt an ugly girl out there with a little make up and exersice to get a hot body BAM! they are miss.universe ;) if you really like him and if you sense him flirting back, then that is a risk
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