53 Questions to Ask Your Crush the Next Time You Talk

Jordyn Taylor
·5 min read
Photo credit: Justin Lambert - Getty Images
Photo credit: Justin Lambert - Getty Images

Even the most confident conversationalists know that talking to a crush can leave you tongue-tied. Not only do you have to come up with a bunch of insightful questions to ask in order to keep the interaction moving, but you also have to make a winning impression. Plus, as the conversation progresses and you learn more about your crush, you also have to do the mental analysis of whether you and this person are actually compatible.

While we can't make that ultimate decision on your behalf, we can help you come up with questions to ask your crush to get to know them better. In learning about certain key areas of their life—namely, their daily lifestyle and interests, their relationship with family and friends, and their communication style—you'll hopefully start to sense whether the two of you could work as a pair, says Jonathan Kirkland, head of marketing and brand for BLK, the largest dating and lifestyle app for Black singles.

"You have to be real with yourself as you continue to get to know your crush," Kirkland says. "If you begin seeing red flags but are still smitten with your initial attraction to that person, you may run the risk of becoming 'colorblind' to these red flags. Pay attention to the person you see in front of you, not the person you think and/or hope that they will become."

Make sense? Great! Remember, when you deploy these, it's normal for your convo to get a little awkward—a lull in conversation isn't necessarily a bad sign. "When you think about it, anything in life that’s new starts off a bit uncomfortably," Kirkland says. "Just work through it, keep going, and enjoy those moments of awkward silence."

Questions About Your Crush's Daily Lifestyle and Interests

"I don’t mean bathing, getting dressed, or bathroom behavior (that would be extremely weird)," Kirkland says. "I’m referring to common activities people do daily: watching TV; listening to music; and other lifestyle habits. Examples: What shows did you binge watch during quarantine? What’s the best '90s R&B group? On a Sunday, would you rather hike Runyon Canyon, or get lit at a boozy brunch?"

Try these:

  1. Are you more of a morning person or an evening person?

  2. Do you ever pull all-nighters, and what for?

  3. What does your ideal Friday night look like?

  4. What does your ideal Sunday morning look like?

  5. What does work/life balance look like to you—and do you think you have it?

  6. What's your favorite part about your job?

  7. What's the most challenging aspect of your job?

  8. What are your top three favorite movies?

  9. What was the last movie you saw in the theaters?

  10. Would you rather go out to eat or cook a nice meal at home?

  11. Do you mostly cook for yourself when you're not at work?

  12. What does your dream vacation look like?

  13. What are your top three favorite books?

  14. What was the last concert you went to?

  15. Where do you get your news?

  16. What are your favorite podcasts?

  17. Do you have any hobbies?

  18. Do you believe in astrology? If so, what's your sign—and do you think it accurately describes you?

  19. Do you post on social media a lot?

  20. What are your favorite accounts to follow on social media?

  21. Coffee or tea?

  22. What are your favorite ways to relax and unwind?

Photo credit: recep-bg - Getty Images
Photo credit: recep-bg - Getty Images


Questions About Your Crush's Relationships With Friends and Family

"If he/she/they seem(s) to frequently be at odds with friends and family, there's a good chance that the real problem here is your crush," Kirkland points out. "Some good questions to ask to get this intel without seeming too intrusive can be: When’s the last time you talked to your parents or siblings? Now that people are getting vaccinated, do you plan on visiting your family, or are you planning any vacations with friends? What was the last group vacation you took with pre-Covid, and how was that?"

Try these:

  1. How did you typically celebrate holidays growing up?

  2. How do you typically celebrate holidays now?

  3. Who in your family typically hosts family gatherings?

  4. What did you do for your birthday last year?

  5. Do you have a big or small family?

  6. Did you get along with your siblings growing up?

  7. Which of your siblings are you closest with?

  8. What do you and your friends do when you hang out?

  9. If you were stranded on a desert island, who in your life would you want to be stranded with?

  10. How do you think your best friend(s) would describe you?

  11. How do you think your family would describe you?

  12. What were you and your friends like in high school?

  13. What were you and your friends like in college?

  14. Do you still hang out with friends from high school/college?

Photo credit: LeoPatrizi - Getty Images
Photo credit: LeoPatrizi - Getty Images

Questions About Your Crush's Communication Style

This is simultaneously one of the most overlooked, yet most important pieces of information to gather when you're getting to know someone, according to Kirkland. "Some people solely text; others love to call and chat. Let’s not forget about the bold ones that will just FaceTime you with no prep time given—and then there are those who can have entire conversations using ONLY gifs and emojis," he says. "A simple question here is basically, 'Are you a phone or a text person?' Then, as you speak more, you'll develop your own little groove of communication."

Try these:

  1. Do you believe in love languages? If so, what are yours?

  2. What Meyers-Briggs personality type are you?

  3. What's your Enneagram number?

  4. Are you more of an introvert or an extrovert?

  5. What apps do you use to chat with people?

  6. Do you like when people send you links to articles they think you'd find interesting?

  7. Do you like when people send you funny tweets and TikToks?

  8. How often do you talk to people on the phone?

  9. How do you feel about conflict, and how do you typically resolve it?

  10. What's your sense of humor like?

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