16. What achievement are you proud of but most people would consider silly or weird?

This question is a great way to find out more about who she really is and what she finds interesting / fun. If the girl you are talking to is a girlfriend you might be able to use that info to create a game / competition that only you and she plays or it might turn out to be great for future gift ideas. However she answers this question, you’ll probably learn something new and interesting about her. Don’t forget to ask a lot about the details.

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20. How would the world change if super heroes and super villains actually existed?

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This is a question to get the creative juices flowing and I’m sure you both can come up with some funny and interesting situations that would arise if super heroes / villains existed. Sure, the girl you are talking to might not be too into this question if they don’t like comics or watching super hero movies. But with how popular super hero movies are, it’s probably a safe bet she’ll enjoy this question. If she doesn’t like those types of movies though, you might want to give this one a pass.
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