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  • Writer's pictureCosmopolitan

Funny Questions to Ask Your Date

Let's say you're forty minutes into a relatively solid date when the conversation comes to a lull. A drink and a half down, you’ve covered hometowns and siblings, bad bosses and slob-y roommates, and playfully debated how old Lorde is, only to clear it up with Google.

Damona Hoffman, dating expert, agrees that some non-forced humor is sure to help you connect. “Humor is the best way to ease tension on a date" she says. So if you’re trying to break the ice or just want to jumpstart the convo on a date, here are the top 30 funny questions guaranteed to make them laugh—or at least, pretend to laugh, and then buy you a drink for trying:


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