Updated: December 10, 2023

121 Best Valentine’s Icebreaker Questions For Work in 2024

You found our list of fun Valentine’s icebreaker questions for teams.

Valentine’s icebreaker questions are prompts to share with your family, coworkers, and loved ones around February 14. Examples include, “What is your dream first date?” and “What is your favorite way to spend Valentine’s Day?” These questions help folks create a stronger connection during Valentine’s parties, date nights, and meetings. These prompts are also known as “Valentine’s Day Questions.”

These prompts are a subset of icebreaker questions and are useful for virtual Valentine’s Day celebrations and Valentine’s Day team building activities.

This list includes:

  • icebreaker questions for Valentine’s Day
  • Valentine’s icebreaker questions for single people
  • Valentine’s icebreaker questions for people in relationships
  • funny Valentine’s icebreaker questions
  • Valentine’s Day would you rather questions
  • Valentine’s Day this or that questions
  • Valentine’s Day questions for students
  • icebreaker questions about love and dating

Here we go!

Icebreaker questions for Valentine’s Day

  1. What is your go-to Valentine’s Day sweet treat?
  2. Do you decorate your house or office with Valentine’s day decorations?
  3. If you were a Valentine’s card, what would you say?
  4. If you were a box of chocolates, which chocolate would you be?
  5. What is your go-to night in rom-com?
  6. What is your favorite flower?
  7. What is your favorite chocolate?
  8. What is the best Valentine’s Day you ever had?
  9. What is the worst Valentine’s Day you ever had?
  10. Do you love or hate Valentine’s Day?
  11. Which celebrity would you most like to be your Valentine?
  12. Have you ever had or ever been a secret admirer?
  13. Have you ever handmade a gift for someone or Valentine’s Day?
  14. Who was your first crush? (Real or fictional?)
  15. What is your favorite love story in a non-romantic movie?
  16. What is the most romantic thing someone has ever done for you?
  17. Have you ever dated someone your friends or family did not like?
  18. What is the worst first date you have ever had?
  19. Have you ever been on a blind date or set someone else up on a blind date?
  20. Have you ever been serenaded or serenaded someone?
  21. Who is your favorite fictional couple?

Valentine’s icebreaker questions for single people

  1. You’ve decided to have a self-care night in. What’s for dinner?
  2. Who is your favorite person to spend Valentine’s day with?
  3. You and your friends are having a single’s night dance party. What are the top three music artists on your playlist?
  4. If you were to make a valentine’s day cocktail or mocktail, what would be the ingredients?
  5. What is your favorite way to spend Valentine’s Day?
  6. What furry friend best represents love to you?
  7. What do you wish people knew or understood about being single?
  8. What is the best part about spending Valentine’s Day single?
  9. Have you ever faked getting engaged at a restaurant to score a free dessert? Would you?
  10. Write a one-sentence love note to yourself.
  11. Who is most likely to send you a Valentine’s present?
  12. What is a relationship dealbreaker for you?
  13. Name one thing that’s more fun to do single than as part of a couple?
  14. Which rom-com best friend is the best?
  15. Share your favorite breakup song.

Valentine’s icebreaker questions for people in relationships

  1. Where was your favorite Valentine’s day date?
  2. What is your favorite love song to dance to together?
  3. If you won an all-expenses paid couple vacation package, where would it be and what would be included?
  4. What do you think your partner’s love language is?
  5. What is the most thoughtful gift your partner has given you?
  6. You come home to find your significant other has made you a 5-course meal of your favorite foods. What’s on the menu?
  7. What celebrity would play your significant other in a movie?
  8. What love song ballad describes your relationship the best?
  9. What is your favorite memory of me?
  10. What surprised you the most about me so far?
  11. How long did your last relationship last?
  12. How long was your longest romantic relationship?
  13. What is your favorite thing to do with me?
  14. What is something that you only do while you are in a relationship?
  15. What might your ex say is your best quality?
  16. What is the most selfless thing you have done for a partner?
  17. What is the silliest argument you have had with a partner?
  18. When or how did you know you wanted to date me?
  19. When was the first time you knew you loved me?

Funny Valentine’s icebreaker questions

  1. If Cupid gifted you his bow for 24 hours, what would you do with it?
  2. What is your go-to pickup line?
  3. What is your silliest date idea?
  4. Can you draw your Valentine’s Day crush in 10 seconds or less?
  5. What cheesy romantic comedy best represents your love life?
  6. Finish the poem– roses are red, violets are blue……
  7. What if they designed packs of Valentine’s cards for adults like they do for school children?
  8. Have you ever had a meet cute or a rom-com moment? What was it?
  9. What is the most embarrassing thing you did because of a crush?
  10. What is the most embarrassing crush you are willing to admit?
  11. What is the funniest bio you have ever seen on a dating site?
  12. What inanimate object would you marry?
  13. Meatloaf once sang, “I would do anything for love, but I won’t do that.” What do you think that “that” is?

Valentine’s Day would you rather questions

  1. Would you rather have a romantic dinner in or enjoy a night out on the town?
  2. Would you rather receive a bouquet of flowers or a stuffed animal?
  3. Would you rather get dressed up or wear something casual on your Valentine date?
  4. Would you rather go salsa dancing or ballroom dancing?
  5. Would you rather buy stor-ebought Valentine’s Day decorations or make them homemade?
  6. Would you rather have a lively group date with friends or keep it one-on-one.
  7. Would you rather have Adele or John Legend serenade your date night?
  8. Would you rather eat a sloppy joe or saucy wings on your first date?
  9. Would you rather have an expensive store-bought gift or a sentimental homemade one?
  10. Would you rather get dumped on Valentine’s Day or have to spend Valentine’s Day with someone you hate?

Valentine’s Day this or that questions

  1. A box of chocolates or sweet tarts?
  2. A home-cooked meal or a fancy restaurant?
  3. Romantic comedy or an Action movie?
  4. Fancy brunch or casual dinner?
  5. Wine and cheeseboards or pasta and cocktails?
  6. Watch the sunrise or watch the sunset?
  7. Go to the zoo or for a hike?
  8. Go to an art museum or the aquarium?
  9. Candlelit dinner or moonlit dinner?
  10. Outdoor Movie or theatrical Production?
  11. Heart-shaped pizza or heart-shaped waffles?
  12. Pink or red?

Valentine’s Day questions for students

  1. What song would you like to be serenaded with in the middle of class by the Valentine’s singing telegram?
  2. What materials are you using to make a homemade valentines card for your crush?
  3. Which 90’s movie would you choose as the theme for your school’s annual Valentine’s Day dance?
  4. If you received a cute stuffed animal from your school crush, what are you naming it?
  5. Would you rather spend your lunch money on a whole bunch of heart-shaped candies or a whole heart-shaped pizza?
  6. Who was the last person who told you “I love you?”
  7. If you could marry anyone in the world, who would you choose?
  8. Would you dress up like Cupid and go out in public for $100?
  9. If you could design a Valentine’s Day card, what would be on it?
  10. Name five things you love.
  11. What is love, to you?
  12. What is your favorite song about love?
  13. If you were to design a dating site, what would it be like?
  14. What is your favorite Valentine’s Day food?

Icebreaker questions about love and dating

  1. What is your dream first date?
  2. Where is your favorite spot to have a romantic picnic?
  3. When is a moment you have felt the happiest?
  4. When is a time you have most felt loved?
  5. If you could go on a honeymoon anywhere in the world, where would you go?
  6. How do you best receive love?
  7. How do you best express your love?
  8. It’s your 50th anniversary. Who are the top 5 celebrities coming to celebrate with you and your boo?
  9. What is your love language?
  10. Would you ever consider an arranged marriage? Why or why not?
  11. Have you ever found a partner through online dating?
  12. What do you think is the most important quality in a partner?
  13. What do you most look for in a relationship?
  14. If you could find out everyone who ever had a crush on you, would you?
  15. Was there ever a time when someone was flirting with you and you didn’t realize it until it was too late?
  16. Which relationship or date do you wish you could do over?
  17. If you had a time machine, what romantic warning would you give your younger self?

Final Thoughts

Valentine’s Day icebreaker questions are a fun way to celebrate love in the office, with friends, or with loved ones. Whether you are connecting with your coworkers or your boss, these prompts icebreakers can help bring a team or workplace together with a bit of lighthearted fun. Since love is one of the universal human emotions and many folks have strong feelings about the feeling, this conversation topic can inspire natural connection and bonding.

FAQ: Valentine's icebreakers

Here are answers to common questions about Valentine's icebreakers.

What are some good Valentine's Day icebreaker questions to ask coworkers?

Asking co-workers the gifts they would like to receive as well as how they like to spend their day is always a win-win. You will not only be able to learn more about their taste and style, you can also gain ideas on how you would like to spend your Valentine’s Day in the future. By using fun icebreaker questions like these, you are able to learn a little bit more about your co-workers and get a little more insight into the things that help to make them happy.

How can you use Valentine's icebreakers at work?

Valentine’s Day icebreakers can be used at work as the start to a meeting, work lunch, and team social in the office to mix things up and add in some fun elements to the workplace.

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People & Culture Director at teambuilding.com.
Grace is the Director of People & Culture at TeamBuilding. She studied Industrial and Labor Relations at Cornell University, Information Science at East China Normal University and earned an MBA at Washington State University.

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