Should you? Is it a smart move? I've liked her for a long time now... So long I'm embarrassed to say.
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I have before. I had no intentions on being her boyfriend, but I did it anyways. I also blatantly told her that I was looking down her shirt and that I could see most of both her tits. She didn't really care. During a field trip around that time, she started randomly grabbing my leg on the bus while I was half asleep. We've been friends for over a decade, it's all good.