50 First Date Questions for Engaging Conversations

Key Takeaways

• Asking engaging, open-ended questions can help break the ice and keep first date conversations flowing.
• Focus on curiosity and thoughtful responses to build a more genuine connection.
• Take your time, stay present, and reflect on how the interaction made you feel to decide if you want a second date.

On a first date, the right questions can help you break the ice, spark a conversation, and get to know someone new. The best questions are open-ended and encourage your date to share more beyond a simple yes or no.

Good first date questions help you get to know the other person’s personality, values, and interests more. These questions also help keep the conversation flowing and leave the other person with a great first impression.

Michela Buttignol / Verywell Mind / Getty Images

Fun and Light-Hearted Questions

1. What’s your favorite meal?
2. What does your ideal weekend look like?
3. What’s the most fun thing you’ve done recently?
4. What’s your favorite way to unwind after a long day?
5. Who’s your celebrity crush?
6. What was your dream job when you were a kid?
7. What kind of music do you like?
8. What’s your favorite book/movie/show/podcast?
9. Do you prefer the outdoors or indoors?
10. What’s the best trip you’ve ever taken?
11. What’s the most bizarre dream you’ve ever had?
12. What’s one thing you can’t leave home without?
13. Which is your favorite place in the world?
14. What’s the most embarrassing nickname you’ve ever had?
15. What’s the most adventurous thing you would like to do?
16. What’s the most hilarious thing that’s ever happened to you on vacation?
17. What’s your hidden talent?
18. What’s the weirdest food combination you’ve ever tried that turned out to be surprisingly great?
19. Do you have a favorite word that you think is just delightful to say or hear?
20. What’s the most surprising fact you know that always blows people’s minds?

Deep and Meaningful Questions

1. What’s your best quality?
2. What’s your worst quality?
3. What does “home” mean to you?
4. What’s your favorite childhood memory?
5. Who are your role models?
6. What is your relationship with your family like?
7. What is your idea of happiness?
8. Where do you see yourself five years from now?
9. What goal are you working toward right now?
10. What’s the biggest challenge you’re facing right now?
11. What does retirement look like to you?
12. What’s a skill or quality you would like to develop in yourself?
13. Have you ever experienced a life-altering moment that changed your perspective?
14. What do you consider your biggest accomplishment so far?
15. What’s the most difficult thing you’ve ever been through?
16. How do you cope when you’re upset or stressed out?
17. What are you most grateful for?
18. What’s the best piece of advice you’ve ever received?
19. What’s your worst habit?
20. If you could change one thing about yourself, what would it be?

Asking these types of questions can help you get to know one another better and may even help spark feelings of connection. One study found that people tend to feel more connected to others when they engage in deep conversations compared to those that are more superficial.

Questions to Keep the Conversation Flowing

If there’s a lull in the conversation, you can ask your date a hypothetical question to spark the conversation and re-engage them. These are some questions that can help you fill an awkward silence:

1. If you could have any superpower, what would you pick?
2. If you could travel anywhere in the world right now, where would you go?
3. If you could switch lives with someone for a day, who would it be?
4. If you had three wishes, what would you ask for?
5. If you could go back in time and witness a historical event, which one would you choose?
6. If you could have dinner with anyone (living or dead), who would you pick?
7. If you could invent one thing right now, what would it be?
8. If you could befriend any animal, which would it be?
9. Which movie best represents your life?
10. Which actor would you pick to play you in a sitcom about your life?

Researchers have found that while long gaps in conversations tend to feel awkward for strangers, these pauses in conversation aren’t a problem for people who are more familiar with one another. Asking the right questions on a first date can help you get to know one another and overcome that initial awkwardness, so these moments eventually feel more like natural moments of mutual reflection.

Other Helpful Questions

Of course, there are plenty of other questions you may want to ask. Some questions may arise as the conversation unfolds. In other cases, you might want to focus on questions about things that are important to you when it comes to compatibility. Other questions you might consider include:

• What kind of things do you value most in friendship or a relationship?
• Are there any causes or issues that are very important to you?
• Have you ever been in a serious relationship?
• What are you looking for in a relationship? Something casual? Serious? Long-term?
• Do you prefer to call or text your partner?
• How do you handle work-life balance?
• What kinds of things do you like to do when you need to relax?

Tips for Making Conversation on a First Date

Going on a first date can be equal parts exciting and nerve-wracking. You may wonder how to introduce yourself, what questions to ask, and how to keep the conversation going.

If you’re in this situation, you’re not alone. “It’s completely normal to be nervous for a first date,” says Sabrina Romanoff, PsyD, a clinical psychologist who specializes in relationships.

Dr. Romanoff shares some tips that can help you prepare for a first date:

• Keep a list of potential conversation topics: If you tend to feel nervous or anxious, it can be helpful to keep a list of potential conversation topics on your phone. The list could include questions to ask as well as funny anecdotes you can talk about. Knowing you have this list in case you get nervous and freeze up can help you relax on the date.
• Ask open-ended questions: Open-ended questions invite people to talk about their feelings and share more information about themselves.
• Listen actively: Pay close attention to what your date is saying. Ask follow-up questions to show them you’re interested. For example, if you ask them which magic power they want and they respond, you can ask them why.
• Avoid conducting it like an interrogation: No one wants to feel like they’re being interviewed or sized up while they’re on a date. Avoid focusing on your date’s resume or the list of schools they’ve been to.
• Focus on genuinely getting to know the person: The best way to get to know someone in a genuine way is to learn about the details of their life and what gets them excited. For example, you can ask about their morning routine, their favorite dessert, or how they spend their Sundays.
• Look for common ground: Try to build a bond with the person by identifying shared interests and creating experiences together during the conversation. The best conversations involve talking about the things that enliven you both. 
• Keep your expectations realistic: Some people are so focused on finding a life partner that they place unrealistic pressure on the first date by forcing a stranger into an imaginary archetype of their life partner. This puts way too much pressure on the date and can quash all spontaneity and fun. Instead, lower your expectations for the first meeting to simply determine whether you want to spend more time with this person.
• Don’t feel pressured to prove your worth: It’s common for people to feel pressure to prove their value or worth to the other person on a first date. This skews the power dynamic and puts you at a disadvantage. Instead, a helpful phrase to remember is “You’re buying, not selling.”

Verywell Mind uses only high-quality sources, including peer-reviewed studies, to support the facts within our articles. Read our editorial process to learn more about how we fact-check and keep our content accurate, reliable, and trustworthy.

1. Kardas M, Kumar A, Epley N. Overly shallow?: Miscalibrated expectations create a barrier to deeper conversation. Journal of Personality and Social Psychology. 2022;122(3):367-398. doi:10.1037/pspa0000281

2. Templeton EM, Chang LJ, Reynolds EA, Cone LeBeaumont MD, Wheatley T. Long gaps between turns are awkward for strangers but not for friends. Philos Trans R Soc Lond B Biol Sci. 2023;378(1875):20210471. doi:10.1098/rstb.2021.0471

3. Kuhn R, Bradbury TN, Nussbeck FW, Bodenmann G. The power of listening: Lending an ear to the partner during dyadic coping conversations. J Fam Psychol. 2018;32(6):762-772. doi:10.1037/fam0000421

By Sanjana Gupta

Sanjana is a health writer and editor. Her work spans various health-related topics, including mental health, fitness, nutrition, and wellness.

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