I am just going to come out and say it: I am probably the absolute worst person to take on a date. If I could even get a girl to listen to me long enough to ask her out, I would praise the heavens for the greatest miracle since sliced bread. It is simply dangerous to date me, not because I am a wanted man, but because I would bore some poor girl to death. The second thing that is necessary when asking a girl on a date is to actually know her as a person. I recommend getting to know the person until you are friends, then just ask the question. If she is interested, great, if not, be polite and move on.
Not really seeing each other much at first due to the fact that you met during summer vacation, but becoming relatively good friends once school starts back up.
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Discovering that you both have an interest in the same type of music and going on random trips to the record store.
Becoming even closer once the news of the Black Hood broke out.