This article was reviewed by John Keegan and by wikiHow staff writer, Bailey Cho. John Keegan is a Dating Coach and motivational speaker based in New York City. With over 10 years of professional experience, he runs The Awakened Lifestyle, where he uses his expertise in dating, attraction, and social dynamics to help people find love. He teaches and holds dating workshops internationally, from Los Angeles to London and from Rio de Janeiro to Prague. His work has been featured in the New York Times, Humans of New York, and Men's Health.
This article has been fact-checked, ensuring the accuracy of any cited facts and confirming the authority of its sources.
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Looking to learn more about someone—say, your crush or a cute stranger—and strengthen your connection? Playing a game of 21 Questions is the best way to deepen your bond, whether you’ve just met or you’ve known them for years. In this article, we’re providing the ultimate list of fun, freaky, and flirty questions to break the ice and take your relationship to the next level.
Fun & Flirty Questions to Ask Your Crush
- Do you have any phobias?
- What’s your biggest guilty pleasure?
- What’s your idea of the perfect date?
- Who’s the hottest person in the room?
- What was your first impression of me?
- Do you prefer being single or in a relationship?
- If you could live in any fictional world, where are you going?