Pinkie Pie: Pinkamena Diane Pie 1,626 members · 1,863 stories
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Even if you two are just aquaintences, I personally do think she would say yes. I also think she'd have no problem telling you "you're boring!" and hopping off to find something more fun to do if you weren't able to keep her interested.

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She wouldn’t want to let anybody down, so she’d indeed say yes. However, I’m fairly certain that if she wasn’t comfortable with the romantic aspect of it, she could always turn it into an “acquaintances-to-friends date” or something similarly harmless.

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