61 Questions to Ask on a Date

The basics:

  1. Where did you grow up, and what was it like?
  2. Do you have any siblings, and what’s your relationship with them like?
  3. What’s your favorite way to spend a weekend?
  4. Do you prefer a night out or a night in?
  5. What’s your go-to comfort food?
  6. What’s something you’re really passionate about?
  7. Do you have any hobbies or activities you love?
  8. Have you ever tried something new that totally surprised you?
  9. Do you enjoy traveling? If so, what’s your dream destination?
  10. Are you more of a book person, a movie person, or both?

Work & Ambitions

  1. What do you do for a living, and do you enjoy it?
  2. If you could have any job in the world, what would it be?
  3. What motivates you to get up in the morning?
  4. Do you consider yourself more of a planner or someone who goes with the flow?
  5. When you were a kid, what did you want to be when you grow up?

Personality & Values

  1. Are you more introverted or extroverted?
  2. How do you usually handle stress or tough situations?
  3. What’s something you really value in a friendship or relationship?
  4. What’s your love language? (Words of affirmation, acts of service, receiving gifts, quality time, or physical touch?)
  5. Do you believe in astrology, and if so, what’s your sign?
  6. Are you a family person? Are you close with your parents/siblings? Do you want children?
  7. Do you want to marry? What would be your dream wedding and honeymoon?

Fun & Lighthearted

  1. What’s the most spontaneous thing you’ve ever done?
  2. What's the most embarrassing situation you've ever been in?
  3. Do you have a favorite TV show or movie you never get tired of?
  4. What’s a fun fact about you that most people don’t know?
  5. What’s your idea of a perfect date?

Funny & Quirky

  1. If you had to describe yourself using only a meme, which one would it be?
  2. What’s the weirdest food combination you actually love?
  3. If you were a superhero, what would your superpower be?
  4. What's the strangest food you have ever tried?
  5. If your life were a movie, what would the title be?

Pop culture & Entertainment

  1. What’s the last TV show you binged and loved?
  2. If you could be in any reality show, which one would it be?
  3. What’s your guilty pleasure song that you secretly jam out to?
  4. Who’s your celebrity crush?
  5. If you had to live in a fictional universe, which one would you pick?

Spontaneous & Adventurous

  1. What’s the most spontaneous thing you’ve ever done?
  2. Would you rather go skydiving or swim with sharks?
  3. What’s the craziest place you’ve ever traveled to?
  4. If we had to go on a random road trip right now, where would we go?
  5. What’s something totally random you’ve always wanted to try?

Personal & Playful

  1. What’s your go-to karaoke song?
  2. If you could only eat one type of cuisine for the rest of your life, what would it be?
  3. What’s the worst haircut you’ve ever had?
  4. Do you have a childhood nickname that’s embarrassing?
  5. What’s the most ridiculous thing you believed as a kid?
  6. What's the worst date you've ever been on?
  7. What was the best day of your life so far?
  8. Have you ever lost a bet? Which one?
  9. What's the weirdest place you have had sex?

Flirty & Lighthearted

  1. What’s your favorite way to spend a lazy Sunday?
  2. What’s your ideal "treat yourself" day?
  3. Would you rather go on a romantic dinner date or do something adventurous together?
  4. What’s the most fun date you’ve ever been on?
  5. What’s one thing about you that I should definitely know before we go on a second date? 😉

LGBTQ+ Questions:

  1. When did you first realize or embrace your identity, and what was that journey like for you?
  2. How was your coming out?
  3. How do you feel about labels - do you find them empowering, limiting, or just useful?
  4. Have you ever been to a Pride event? If so, what was your favorite part?
  5. Have you ever had a “gay awakening” moment from a movie or celebrity? (Who was it?)
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