200 Fun, Flirty, & Deep Questions to Get to Know a Guy Better


Spark a great conversation with these revealing icebreakers for him

This article was co-authored by Laura Bilotta and wikiHow staff writer Bailey Cho. Laura Bilotta is a dating coach, matchmaker and founder of Single in the City, her dating and relationship coaching service based in Toronto, Ontario, Canada. With over 18 years of experience, she’s focused on helping singles date more intentionally, encouraging them to break free of negative patterns so they can attract the love they deserve. Her experience, skills and insight have led to thousands successfully uniting over 65,000 singles through one-on-one matchmaking events and sessions. She has hosted The Dating and Relationship Show on Global News Radio 640 Toronto (AM640) for 6 years and is known as The Hookup Queen of Clubhouse; her popular singles club, Single in the City, has over 95,500 members who regularly join the weekly dating and hookup rooms. This article has been fact-checked, ensuring the accuracy of all facts cited and confirming the authority of its sources.

Trying to learn more about your boyfriend and deepen your relationship? Asking interesting questions is the best way to connect with someone, whether you’re chatting via text or in person. In this article, we bring you the ultimate list of fun, flirty and interesting questions you can ask your boyfriend to get to know him better. We also talked to dating experts Lauren Sanders and Laura Bilotta for tips on how to break the ice and deal with social anxiety while dating.

  1. What’s your death row meal?
  2. What brings out your inner child?
  3. What is your favorite way to relax?
  4. What’s one thing on your bucket list?
  5. What was your first impression of me?
  6. Would you rather have more time or more money?
  7. What’s the best advice you’ve ever received?
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Categories: How to
Source: HIS Education

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