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First Date Questions

Looking for the best first date questions? Choosing the right questions to ask on a first date might seem easy. But it can be overlooked in the midst of pre-date nerves and the search for the ideal wardrobe.

While it’s important to fill any awkward pauses in conversation, it’s also important to move past the superficial into deeper conversation to genuinely get to know the person you’re out with.

So, if you’re always worried about what to say, relax. We have you covered with a wide variety of interesting questions to ask, as well as commentary from the pros on why certain inquiries are helpful for learning more about your date.

First date questions
First date questions

Good first date questions

1) Where do you like to travel

2) When you’re not busy, how do you like to spend your time?

3) Do you prefer being indoors or outdoors?

4) Who, specifically, have you found to be the most fascinating encounters in your life?

5) In what book did you last lose yourself?

6) What are some good movies that you’ve seen recently?

7) How many different pets have you owned?

8) Specifically, what is it about foreign cuisine that you enjoy the most?

9) Which TV shows do you find yourself watching over and again?

10) If you had limitless resources, what activities or interests would you pursue?

Expert advice: While it may sound odd, studies have found that we are more attracted to people who have more mimicry in their behavior. Mirroring, which is the act of behaving and showing body language similar to the other person, is an effective technique to use on first dates.

First date questions
First date questions

My experience asking questions on the first date…

Here’s the thing, you are going to need to talk with your date about something… Typically, a woman is going to expect the guy to start the conversation. And to maintain it.

As a guy… well, this is really hard. Because you have to think creatively and also balance noting how she’s responding to certain questions.

Here are my BEST tips…

  • Try any question – The first tip is don’t be afraid. Try any question. And see how it goes.
  • Keep a few in your back pocket – Don’t be afraid to pick out your favorites and ask them from time to time.
  • Ask questions for you – Don’t forget that this date is about you, too! Ask questions that will help you to figure out if the person is a good match for YOU, not just the other way around.

Basic but essential first date questions

1) What’s your dream job?

2) Are you a morning person or night owl?

3) What does your ideal second date look like?

4) How do you picture your own life going?

5) What’s your favorite international food?

6) How do you make first dates less awkward?

7) What’s your favorite ice cream flavor?

8) How many kids do you want to have?

9) What relationship advice would you give to others?

10) What’s your first impression of me?

11) What’s your favorite holiday?

12) What was the best meal you ever ate?

13) What is something that’s on your bucket list?

14) What is your favorite food?

15) Do you have any pet peeves?

16) Who are your favorite musicians?

Related: Funny first date questions

First date questions
First date questions

Best questions

—The very best first date questions

1) Describe the most thoughtful present you’ve ever given?

2) What do you consider to be the most helpful piece of advice you’ve ever received?

3) How would you sum up your day, typically?

4) Have you recently been to any restaurants that you would consider to be exceptional?

5) Do you spend a lot of time around here?

6) Who or what motivated you to pursue your career?

7) How would you best describe your greatest skill?

8) Are there specific causes that you support?

9) Can you tell me about some of the things you hope to accomplish in your life?

10) Which musician you like most and never get tired of listening their songs?

Expert advice: A study from Purdue University has suggested that our “sweet taste buds” can have an effect on our short-term happiness, causing us to feel a stronger attraction to those around us. What does this mean for first dates? Don’t skip the sweets!

Funny questions

Funny first date questions

1) What age would disqualify a person from your dating pool?

2) Have you ever wanted to be a cartoon character? If so, who is it?

3) Have you ever sent a drunken text to someone you later regretted?

4) Have you ever faced an embarrassing situation on a date?

5) Have you ever, while complaining about someone else, accidentally sent a text message or email to that person?

6) What is the dumbest joke you’ve ever told?

7) What was the strangest thing you did as a kid that you’re still embarrassed about?

8) What would your ideal superpower be if you had the chance to choose one?

9) What is the most hilarious dream you’ve ever had?

10) What are some of the most memorable pranks you’ve played on people?

Deep questions

—Deep first date questions

1) Which of your seemingly insignificant choices has had the greatest bearing on the course of your life?

2) Which year do you consider to have been the best year of your life up to this point?

3) what would you do differently if you knew you only had six months to live?

4) How much effort did you put in to accomplish your greatest success?

5) How would you describe the friendship that has meant the most to you?

6) Describe some of the scenarios you always attempt to avoid.

7) When deciding between love and loyalty, which do you prize more?

8) When is it that you ask others to give you the most space?

9) What is the craziest thing that any person has ever said to you?

10) What is the current subject of your obsession?

For a guy

1) How strongly do you believe in fated relationships?

2) What would you do if money were not an issue?

3) What does it mean to you to have masculinity or to be a man and what does it entail?

4) What happened when you finally told your first crush about it?

5) What is the one thing about you that drives other people absolutely insane?

6) What is the most insignificant aspect of your life that you consistently lie about?

7) Is there anything specific about dating that really gets on your nerves?

8) What is one fact about you that always seems to take people by surprise?

9) In what ways are you truly exceptional?

10) What characteristics do you look for in a potential partner?

For a girl

1) What have you been up to this summer?

2) Do you ever find yourself watching sports on television?

3) How often do you attend concerts?

4) Do you have any experience traveling to foreign countries on your own?

5) Which dance style do you prefer the most, and why?

6) What do you consider to be the most important possession you’ve ever owned?

7) Where in the world would you most want to make your home if you had the choice?

8) What is it that you enjoy doing most when you have the whole day to yourself?

9) How would you describe the ideal weekend?

10) At what age do you believe a person should “grow up,” and why do you hold this belief?

Flirty first date questions

1) When was the most recent time you had butterflies, and what caused them?

2) When you think of the qualities you find most appealing in a male partner, what comes to mind first?

3) If you had to pick one thing that you did that was the most romantic thing you’ve ever done, what would it be?

4) Do you like to snuggle up or get kissed more?

5) Do you harbor any deep-seated desires that no one else knows about?

6) What is the something that gets your blood pumping the most?

7) Which would you choose, a million dollars or true love?

8) Which option, remaining friendly with an ex or cutting off all contact, would you prefer?

9) Which do you prefer, dancing under the stars or in a nightclub?

10) If you had to choose between Starbucks and a small coffee shop, which one would you choose?

Spicy first date questions

1) What are your thoughts on the concept of a woman making the first move in a relationship?

2) How important is it for you to have a partner that you can get naughty with?

3) When it comes to dating, what has been the biggest letdown for you so far?

4)Have you ever been involved in a relationship that lasted only one night?

5) Which piece of clothing that women wear does it seem most appealing to you?

6) What kind of music do you typically listen to when you’re in the bedroom?

7) Is there anything you’d like to ask your ex if you two were to have a conversation?

8) Whose relationship do you admire, and why is it so special to you?

9) What was the most recent flirtatious text that you sent to someone?

10) What do you consider to be the most embarrassing thing you’ve ever worn?

Juicy first date questions

1) What do you put on when you go to bed at night?

2) Which word or phrase did you most recently look up on your mobile device?

3) Does it make a difference if you’re big or small?

4) Who was the person you kissed that was the most embarrassing for you?

5) Do you believe that people run into each other for a purpose or does chance play a role?

6) When you see a hot person, how do you resist the urge to be attracted to them?

7) When was the last time you dreamt about the person you have a crush on?

8) If you had to choose between your favorite celebrity role model and your best friend for the rest of your life, who would you choose?

9) Which would you rather do: spend two hours together watching a movie or playing hide and seek?

10) Who is the person in your life who is most likely to always be honest with you, regardless of what transpires?

Icebreaker first date questions

1) What’s something that’s tedious but totally rewarding?

2) If you had the choice, which would you prefer: a sedentary lifestyle or an active life?

3) When you were a kid, what did you always picture yourself doing when you got older??

4) Describe the perfect version of a website or mobile app that does not yet exist.

5) What is the piece of advice that turned out to be the worst you’ve ever received?

6) What item do you always make sure to buy when you go grocery shopping?

7)Would you rather remain single for the rest of your life or marry someone because your parents pressured you to do so?

8) Which four applications would you choose to keep on your smartphone if you were forced to delete the rest?

9) If you could choose between being the center of attention and being alone, which would you choose?

10) Which of Wikipedia’s many digressions do you consider to be the most peculiar?

Awkward first date questions

1) When was the last time you went in for a checkup?

2) How Do I Differ From My Online Presence Or Your Initial Impression Of Me?

3) Is this your natural skin tone?

4) Why are you not dating anyone?

5) What is your ethnic background exactly?

6) Do you or did you ever have to worry about your weight?

7) I need an accountability partner, would you be interested?

8) So you own your own condo? How much did it cost you?

9) Are you content with the path your career has taken?

10) How many children do you hope to have someday?

Christian first date questions

1) Can you describe the day that stands out as the highlight of your entire life to this point?

2) What are the three things that, if you could make sure you did them before you died, they would be?

3) Can you describe your spiritual awakening and how you found salvation in Christ?

4)Can you describe a time when God radically altered your perspective on something?

5) How would you describe the state of your relationship with your parents right now?

6) Can you tell me about your top three closest friends?

7) When was the first time you felt like you weren’t being treated fairly?

8) How often do you pray for God’s guidance before making important choices?

9) What religious group is your church, and how often do you attend?

10) Having a relationship with Jesus, what does that mean to you, and how does it change your life?

Important first date questions

1) When you’re not working, what do you do to relax?

2) Can you recommend a good book, or perhaps a particular writer?

3) In what organizations do you participate?

4) Where in town do you like to spend most of your free time?

5) Is there something special you’re keeping to yourself?

6) Where do you typically get your food when you want it delivered?

7) Exactly which flavor of frozen dessert do you relish the most?

8) You are only allowed to bring three items with you to an island that is completely deserted. What do you bring?

9) What special things would you buy for yourself if you got lucky and won the lottery?

10) Tell us about some of your favorite reel artists that you like to watch.

Personal first date questions

1) Do We Have The Same Things That Can Make or Break a Deal?

2) Do You Have More Than One Person in Your Life Who You Consider to Be Important?

3) Do You Have A Dog Of Your Own?

4) What Is It That You Take the Most Pride In?

5) How many times have you been married before?

6) How Would You Describe the Feeling of Complete Contentment?

7) How did the two of you become such good friends?

8) Are you still close with your high school buddies?

9) Suppose you had to make a charitable contribution, which organization would you choose and why?

10) When the going gets rough, what do you do to relax?

Weird first date questions

1) What is the backstory of your first kiss?

2) Which would be your preferred dating reality show if you had to go on some?

3) Which internet meme do you find yourself referring to most frequently?

4) What are some of the nicknames that people in your family and circle of friends call you?

5) How about your most cheesy pickup line—does it work?

6) How often do you date members of the same gender as you?

7) In your opinion, which dinosaur would have the best flavor?

8) With a year to live, how would you spend your time?

9) Are you someone who donates organs?

10) Is anyone else aware that you’re here?

Random first date questions

1) What drew you to this particular location?

2) What did you do over the past weekend?

3) What are your thoughts on the various social media platforms?

4) Do you value spending time with your family a lot?

5) Where did you go on your most recent vacation?

6) What major did you pursue?

7) Do you like being surprised?

8) What is it that you find yourself usually fixated on these days?

9) If asked an opinion, what are some activities that everyone should engage in at least once?

10) What’s your favorite humorous anecdote to tell whenever people ask?


Fact checked:
Board reviewed by Marianne Tomlinson, LCSW (Couples and Family Therapy). Content is rigorously reviewed by a team of qualified and experienced fact checkers. Learn more.

About the author

Ryan Sanderson (LCSW) Ryan is a game and relationship enthusiast who enjoys all things quizzes, games, fun, love, relationships, and family. He's a licensed social worker and helps families, couples, and children in need. He's spoken about love and relationships on Salon.com, Forbes, and Mirror, to name a few.

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