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First Date Questions to Get To Know Someone Deeper

first date questions

A first date can be a lot of pressure. Maybe you’ve been chatting over text for a while now, or maybe you’ve been friends and this is your first foray into romantic entanglement. Whatever the case is, you’re likely feeling a bit nervous. What if it’s awkward? What if there’s a lull in the conversation? What should I say? What if I talk too much? 

These are normal concerns, and one way to put your mind at ease is to prepare a list of questions you want to ask your date. The goal here is not to conduct an interview, but, rather, to get to know someone genuinely on a deeper, personal level. 

This is the first article in our new “Healthy Relationships” Series. Stay tuned for more content on how you can build a healthy, thriving relationship. 

First Date Etiquette: How to Get To Know Someone

how to act on a first date

The best first-date questions are paired with a curious, respectful demeanor. It doesn’t matter how good of questions you ask if you don’t listen to their answers. Here are some things to keep in mind as you embark on your first date:

  • Keep a list of questions ready: These questions should be important to you. For example, if religion is important, ask them about their spirituality. 
  • Ask open-ended questions: Avoid lulls in the conversation by asking questions that must be answered with more than a simple yes or no. 
  • Listen actively: Respond to what they said before launching into your own anecdotes. You may feel pressure to show your date the deepest parts of yourself on the first date, but remember this is a time to get to know them, too. 
  • Hold a conversation, not an interview: There is probably a list of boxes you want your partner to check off, and that’s fine. There’s nothing wrong with having expectations! But try to have a conversation with them on their first date so you can get to know their personality, conversation style, and how well they listen. They may look great on paper, but these are the things that will determine the strength of a long-term relationship.
  • Know your worth: Don’t focus so hard on selling yourself. First dates can be stressful because you want them to like you, but the stakes are relatively low. Maybe they decide they don’t want a second date, then what? It’s disappointing, sure, and maybe you felt like you wasted an afternoon. But in the end, feelings were spared because you never pretended to be someone you weren’t and didn’t get caught up in a situationship that would have hurt you. 

Conversation can be hard to maintain when you’re on a first date. Awkwardness and first-date jitters are hallmarks of a first date. To keep the conversation running smoothly, here are 58 questions you can ask on a first date. 

58 Questions to Ask a Guy or Girl on a First Date

The day of your first date is here, congrats! You successfully moved what was likely an online conversation or a mutual friend arrangement into the real world, with a set location and time. Nervous? Don’t be. Take a few of these deep conversation starters to launch a revealing and great first date.  

first date questions

Ice Breaker Questions

You probably don’t want to jump in with “so what’s your relationship with your parents like”, but you don't ramble on about the weather either. Here are some icebreaker questions to ask your crush as you start to warm up to one another. 

  1. Who’s your celebrity crush?
  2. What kind of music do you like?
  3. What’s the best trip you’ve ever taken?
  4. What’s one thing you can’t leave home without?
  5. If your house was burning and you could only carry one thing out, what would it be?
  6. What’s your hidden talent?
  7. If you could live anywhere in the world, where would it be and why? 
  8. What’s your hottest take or most unpopular opinion? 
  9. What song would you sing karaoke to? 
  10. What’s a conspiracy theory you kind of believe in?

Questions to Get to Know Someone

The conversation has been rolling along lightheartedly. Maybe there were some laughs and excellent eye contact. Now it’s time to dig a little deeper and find out who they are. 

  1. What does your work-life balance look like?
  2. What would you do if you had a week off?
  3. Who do you talk to the most?
  4. What is the best gift you’ve ever received?
  5. What does your ideal weekend look like?
  6. What do you like to do outside of work?
  7. Are you more of an introvert or an extrovert?
  8. What are some of your pet peeves?
  9. What is something you could rant about?
  10. What did you want to be when you were a kid? What changed? 

Deep Conversation Starters

The time feels right, and you want to go a little deeper. Don’t fumble a potentially awkward opening when asking deeper questions and use these deep conversation starters. 

  1. What matters to you?
  2. What does your dream life look like?
  3. What is something you want to change about yourself?
  4. What is your greatest strength? 
  5. What is your greatest weakness?
  6. What’s something no one else knows about you?
  7. What type of roommate are you? 
  8. What’s your relationship like with your family?
  9. What does “home” mean to you?
  10. What’s your favorite childhood memory?
  11. What does happiness look like to you?
  12. What goal are you working toward right now?
  13. What’s the biggest challenge you’re facing right now?
  14. What’s the most difficult thing you’ve ever been through?
  15. What are you the most grateful for?
  16. What’s the best piece of advice you’ve ever received?
  17. What’s your worst habit?
  18. What’s been on your mind a lot lately?
  19. What’s your attachment style
  20. If you could, how would you change the world?

Compatibility Questions

It’s time to whip out that list. A first date is a great time to figure out if a future relationship is even possible. Are there any deal breakers? Find out with these first-date questions. 

  1. What made you interested in going out with me?
  2. What are you looking for?
  3. How well do you feel like you compromise with others?
  4. What do you think is important for a healthy relationship?
  5. How do you handle conflict?
  6. What was your first impression of me?
  7. Do you want a family? How far into the future do you want that?  
  8. What are some non-negotiables you need in a partner?
  9. How long was your longest relationship? Why did it end?
  10. How much conflict do you think is healthy in a relationship?
  11. What is your love language?
  12. How do you deal with jealousy?
  13. Do you believe in love at first sight?
  14. How much alone time do you need?
  15. What does quality time look like to you?
  16. Do you care if your partner makes more money than you do?
  17. What are your deal breakers?
  18. What goals do you have for a relationship? 

See also: 10 Relationship Goals every Couple Should Have

Be Authentic

The best piece of advice is to simply be yourself. If they don’t like you for you, then they aren’t the right person for a long-term relationship. Don’t change yourself to fit the expectations a first date has for you, but approach them with an open mind and curiosity. Expect the same back. 

First dates can be a long, arduous process, and it might take a few first dates until you find someone to take on a second date. Use this list of questions to get to know people on a deeper level, so you can really know if you’re ready to ask them on a second date.

Are you a few dates in and still struggling to connect? Or, have you lost that spark that you once had? Relationship counseling is a great way to work through foundational issues in your relationship, move through difficult times together, and develop healthier styles of communication. Contact Lifebulb to be matched with a relationship therapist near you. 

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Frequently Asked Questions

When connecting with your boyfriend on a deeper level, consider asking questions that show your interest and care for him. For example:

  • How are you feeling today?
  • What are your short-term and long-term goals?
  • What's something you're passionate about?
  • How can I support you better?
  • What's your favorite memory from our time together?

To strengthen your bond with your girlfriend, try asking questions that showcase your curiosity and desire to understand her better. Here are a few suggestions:

  • What qualities do you value in a relationship?
  • How can I make your day brighter?
  • What are your dreams and aspirations?
  • What makes you feel loved and appreciated?
  • What do you enjoy doing for fun?

When planning a first date, aim for activities that facilitate conversation and connection. Consider options like:

  • Going for a leisurely walk in a scenic park
  • Trying out a new restaurant or café together
  • Visiting a local museum or art exhibit
  • Attending a live music or comedy show
  • Participating in a fun cooking or painting class

To develop a deeper understanding of someone, engage in meaningful conversations and activities that foster openness and vulnerability. Here are some tips:

  • Ask open-ended questions that encourage sharing thoughts and emotions.
  • Listen actively and show genuine interest in their experiences and perspectives.
  • Share your own stories and feelings to create a sense of mutual trust.
  • Spend quality time together engaging in shared interests or trying new things.
  • Be patient and allow the relationship to evolve naturally over time.

Remember, building strong connections takes time and effort, but the rewards of deeper relationships are truly valuable in the journey towards living your brightest life.

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