120+ Deep Questions for *Really* Getting to Know Someone

There’s a time and a place for small-talk, as fake as it can feel. Curious as I’m sure you are, you probably don’t want to ask someone about their deepest sexual desires shortly after meeting them for a first date. But if you want to forge a meaningful connection with someone—be it a possible new friend or romantic partner—you should eventually get to know who they are beneath the surface. Some research has shown that people feel closer after disclosing deep personal stuff versus making small-talk.

Asking the right deep questions (and being willing to answer them when they come back your way) can help you build a strong bond with someone. So, what makes a good deep question? We’d recommend phrasing your query in an open-ended way that encourages the person to elaborate; in other words, don’t ask something they can answer with a simple “yes” or “no.”

It’s the difference between:

“Do you like your job?” (Not open-ended.)


“What do you like about your job?” (Open-ended.)

Here are 100 deep questions to help you learn about another person’s likes, dislikes, hopes, fears, goals, and more.

Deep Questions About Past Experiences

Deep Questions About Romantic Relationships

Deep Questions About Sex

Deep Questions About Identity

Deep Questions About Family

Deep Questions About Career

Deep Questions About the Future

Deep Questions About Death and Aging

Deep Questions About Likes, Dislikes, and Favorite Things

Deep Questions About Space and Time

Deep Questions About Fears and Phobias

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