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Look, getting to know someone can be intimidating, and even when both people are perfectly interesting and the chemistry is there, it's hard to know the right conversation topics to bring up with a stranger. You might be hesitant to ask something too personal when you're just getting to know someone, but you also want to get out of that dreaded small-talk territory—and thwart those equally-dreaded awkward silences. Your childhoods Not in a therapy sort of way! Just in terms of where you grew up, what your interests were in high school, what your hometown was like, and what funny things happened to you as kids. Actually, if high school's involved , maybe it could get a bit therapeutic. Just roll with it. Your families If you don't think to ask up-front, you can actually go a surprising amount of time without even knowing what someone's parents do for a living.