300+ Valentine’s Day Icebreaker Questions for Work colleagues (trivia, riddles, quizzes, truth or dares and more)

Valentine’s Day is the perfect time to bring a bit of fun, connection, and conversation into the office. Whether you’re organizing a team-building event or looking to spice up your Zoom meeting, these icebreaker questions can help bring people together.

Here’s a breakdown of creative and work-appropriate valentine’s day icebreaker questions to ask your colleagues. From Conversation starters, trivia, riddles, quizzes, truth or dares, never have I ever, to would you rather questions.

Importance of Valentine’s Day Icebreaker Questions for Work

Valentine’s Day icebreakers help build rapport, lighten the atmosphere, and promote camaraderie among colleagues. They’re perfect for encouraging team bonding and getting everyone to feel more relaxed in the workplace. These questions can break the ice in meetings, lunches, or casual hangouts, making interactions more engaging and fun. Icebreakers can also provide insight into coworkers’ personalities, fostering mutual understanding and enhancing workplace culture.

Work Appropriate Valentine’s Day Icebreaker Questions for Work Colleagues

How to Play: To make the most of these icebreakers, choose a few questions and either ask them one at a time during a team meeting or leave them on a board where everyone can answer throughout the day. You can go around the room or virtually, asking people to answer one question each.

Dos:

• Keep questions light and inclusive.
• Allow everyone to participate but don’t pressure anyone.
• Let answers be quick and fun to keep the flow going.

Don’ts:

• Avoid overly personal or invasive questions.
• Don’t put someone on the spot to answer if they seem uncomfortable.

Examples:

1. What’s the best piece of advice you’ve ever received about love or relationships?
2. Do you prefer chocolate, flowers, or something else as a gift on Valentine’s Day?
3. If you could spend Valentine’s Day anywhere in the world, where would it be?
4. What’s the most romantic gesture you’ve ever seen or experienced?
5. Who is your celebrity crush, and what would you say to them if you met them today?

Dating Related Valentine’s Day Questions to Ask Your Employees or Team for Deep Conversation

How to Play: These questions are best suited for a one-on-one or smaller group setting. Ask these as part of a team-building exercise or in a relaxed conversation after work hours. They can also be used to create deeper connections during break-time discussions.

Dos:

• Let participants share only what they’re comfortable with.
• Keep the tone respectful and avoid prying into anyone’s private life.

Don’ts:

• Don’t push people into discussing relationships they may not feel comfortable talking about.
• Avoid using these questions in large group settings where people might feel awkward.

Examples:

1. What qualities do you look for in a romantic partner?
2. What’s the best date you’ve ever been on, and why?
3. Do you believe in love at first sight? Why or why not?
4. What’s the most important factor in maintaining a healthy relationship?
5. If you could choose one dating trend from the past, what would it be, and why?

Related: 100 Office Valentine’s Day Ideas: Your Guide to Celebrate Love for the valentine week at workplace

Valentine’s Day Themed Funny and Hilarious Questions to Ask Your Coworkers

How to Play: These questions are ideal for light-hearted interactions. You can start with one funny question and have everyone answer, or send them via email as part of a fun office poll.

Dos:

• Keep it light and humorous; the goal is to get everyone to laugh.
• Ensure everyone feels included in the humor.

Don’ts:

• Avoid questions that could offend or exclude others based on personal experiences or preferences.
• Don’t overdo it with too many jokes at once—balance is key.

Examples:

1. If Cupid’s arrow hit you, who would you want it to strike in the office?
2. If you were a chocolate, what kind would you be and why?
3. What’s the worst Valentine’s Day gift you’ve ever received (or given)?
4. If you had to write a love song for your desk or office supplies, what would it sound like?
5. If you could swap Valentine’s Day gifts with anyone in the office, who would it be and why?

Workplace Valentine’s Day Would You Rather

How to Play: This classic game works well in both small and large groups. Simply ask one question at a time and allow everyone to answer. For a more interactive experience, turn it into a quick-fire round where people have to decide on the spot!

Dos:

• Encourage everyone to elaborate on their answers for fun.
• Keep the pace quick so no one feels forced to overthink their answers.

Don’ts:

• Avoid creating questions that could make others feel uncomfortable (e.g., asking about romantic preferences).
• Don’t make it too long; keep it snappy and fun.

Examples:

1. Would you rather receive 10 boxes of chocolates or 10 bouquets of roses this Valentine’s Day?
2. Would you rather work on Valentine’s Day or have it off for a romantic getaway?
3. Would you rather have a romantic dinner with someone you like or a fun night out with friends?
4. Would you rather be stuck in the office on Valentine’s Day or work from home?
5. Would you rather get a handwritten love letter or a box of gourmet chocolate?

Related: 40+ Valentine’s Day Office Games: Fun Ideas to Spread the Love at Work

Office Themed Valentine’s Day Never Have I Ever

How to Play: Each person shares something they have or haven’t done related to the question. If they have done it, they may elaborate on the experience. You can play this in teams or individually, with each player taking turns.

Dos:

• Keep the statements lighthearted and respectful.
• Ensure everyone feels comfortable participating.

Don’ts:

• Don’t ask questions that could make others feel embarrassed or uncomfortable.
• Avoid making anyone feel excluded if they haven’t had certain experiences.

Examples:

1. Never have I ever sent a Valentine’s Day card to a colleague.
2. Never have I ever celebrated Valentine’s Day alone by choice.
3. Never have I ever had a crush on someone in the office.
4. Never have I ever forgotten to send a Valentine’s Day card to someone important.
5. Never have I ever received a Valentine’s Day gift from a coworker.

Valentine’s Day Ever or Never for Office Staff

How to Play: Ask each participant to share if they’ve done something related to the question. This game works well in larger settings and can be played by taking turns or through anonymous polling tools for virtual teams.

Dos:

• Keep it casual, and let everyone pass if they don’t feel like answering.
• Make sure there’s no pressure for participation.

Don’ts:

• Don’t make anyone feel uncomfortable if they’ve never done something.
• Avoid asking personal or invasive questions.

Examples:

1. Ever gotten a Valentine’s Day gift from a colleague, or never?
2. Ever planned a Valentine’s Day event at work, or never?
3. Ever written a love poem for someone at work, or never?
4. Ever had a secret office Valentine, or never?
5. Ever attended a Valentine’s Day lunch or dinner with your team, or never?

Valentine’s Day Yes or No Questions for Colleagues

How to Play: In this format, ask simple Yes or No questions and let colleagues give quick answers. For more engagement, allow them to explain their choice afterward.

Dos:

• Keep it light and fun.
• Give everyone a chance to speak, but don’t force anyone to elaborate.

Don’ts:

• Avoid controversial or deeply personal topics.
• Don’t overcomplicate the game with too many questions.

Examples:

1. Do you enjoy Valentine’s Day celebrations at the office? Yes or No?
2. Have you ever had a Valentine’s Day date with a coworker? Yes or No?
3. Do you think Valentine’s Day is overrated? Yes or No?
4. Would you rather have flowers or chocolates for Valentine’s Day? Yes or No?
5. Would you celebrate Valentine’s Day in the office if it was your choice? Yes or No?

Related: 150+ Office Valentine’s Day Messages: Spreading Love and positivity to your coworkers, employees and team

Workplace Couples Valentine’s Day Truth or Dare

How to Play: A fun twist on Truth or Dare, ask couples or close coworkers to choose between truth or dare. You can do this in small groups or one-on-one, depending on the team dynamic.

Dos:

• Keep the dares light and fun.
• Respect everyone’s boundaries for sharing truths.

Don’ts:

• Avoid making dares or truths that could be seen as inappropriate or uncomfortable.
• Don’t force anyone to do a dare they’re not comfortable with.

Examples:

1. Truth: What’s the most romantic gesture you’ve made at work?
2. Dare: Give a compliment to your work partner or someone at your desk.
3. Truth: Have you ever had an office crush, and did you act on it?
4. Dare: Send a Valentine’s Day card to someone you admire at work.
5. Truth: What’s the worst Valentine’s Day date you’ve ever been on?

Family Feud (Valentine’s Day Office Edition)

How to Play: Split the group into teams and ask them to guess the most popular answers to the Valentine’s Day-related questions. Keep score to make it more competitive!

Dos:

• Keep it fun and light-hearted; the goal is for everyone to enjoy.
• Let everyone participate equally.

Don’ts:

• Don’t make it overly competitive or serious.
• Avoid questions that might create discomfort or offense.

Examples:

1. Survey says: Name something people do on Valentine’s Day.
2. Survey says: Name a gift people expect to receive on Valentine’s Day.
3. Survey says: Name a popular Valentine’s Day activity.
4. Survey says: Name something you might find on a Valentine’s Day card.
5. Survey says: Name a color associated with Valentine’s Day.

Valentine’s Day Trivia for Work

How to Play: These trivia questions can be asked in a quiz format during a meeting or event. Keep track of the answers to declare a winner at the end.

Dos:

• Keep the questions varied in difficulty for everyone to participate.
• Offer a small prize or recognition for the winning team or individual.

Don’ts:

• Don’t make the trivia too difficult; aim for fun, not frustration.
• Avoid obscure trivia that could alienate participants who are less familiar with Valentine’s Day traditions.

Examples:

What flower is most commonly associated with Valentine’s Day?

• Rose

Who is the Roman god of love, often depicted with a bow and arrow?

• Cupid

Which famous candy company produces heart-shaped candies with messages on them?

• Necco

In which country did the tradition of sending Valentine’s Day cards originate?

• England

Which month is traditionally celebrated as the month of love?

• February

Valentine’s Day Quiz for Workplace

How to Play: Ask each question and let participants take turns answering. You can do this in teams for added interaction or as a solo activity during breaks.

Dos:

• Make sure everyone gets a chance to answer.
• Give small rewards for correct answers to keep it engaging.

Don’ts:

• Avoid asking questions that might be too hard or niche.
• Don’t make the quiz last too long; keep it under 10 minutes for maximum enjoyment.

Examples:

Who is the Greek goddess of love?

• A) Athena
• B) Aphrodite
• C) Hera
• D) Demeter

What year did the first commercial Valentine’s Day card become available?

• A) 1800
• B) 1840
• C) 1900
• D) 1910

Which U.S. president was born on Valentine’s Day?

• A) George Washington
• B) Abraham Lincoln
• C) Theodore Roosevelt
• D) Franklin D. Roosevelt

What is the traditional symbol of love on Valentine’s Day?

• A) Star
• B) Heart
• C) Dove
• D) Rose

In what city would you find the famous “Love Locks” bridge?

• A) New York City
• B) Paris
• C) Rome
• D) London

Valentine’s Day Riddles for Work

How to Play: These riddles can be used to challenge colleagues during breaks or as part of a quick team-building session. Allow everyone a chance to solve each riddle.

Dos:

• Keep the riddles fun and lighthearted.
• Encourage everyone to work together to solve the riddles.

Don’ts:

• Avoid difficult riddles that may frustrate people.
• Don’t overcomplicate the activity; the goal is to have fun!

Examples:

1. What’s the most romantic part of a calendar? (Answer: February 14th)
2. What’s a romantic vegetable? (Answer: A heart-shaped artichoke!)
3. What did the paper say to the pencil on Valentine’s Day? (Answer: “You’re sharp!”)
4. What did one light bulb say to the other on Valentine’s Day? (Answer: “I love you a watt!”)
5. Why did the boy bring a ladder to his date? (Answer: Because he heard the date was going to be a high school dance!)

Here are some more Valentine’s day conversation starters to ask your team:

Work Appropriate Valentine’s Day Icebreaker Questions for Work Colleagues

1. What’s the most creative Valentine’s Day gift you’ve ever given or received?
2. If Valentine’s Day were a holiday for work, what would the ideal celebration look like?
3. What’s your go-to comfort “love song” while working on a deadline?
4. Have you ever received a Valentine’s Day card at work? What did it say?
5. If your job were a romantic comedy, what would the title be?
6. What office supply would make the best Valentine’s gift and why?
7. What’s the most romantic thing you’ve ever seen happen in a movie?
8. If you could redesign the office for Valentine’s Day, what would you add?
9. Which snack in the breakroom do you secretly “love”?
10. What’s your favorite Valentine’s candy to eat while brainstorming?
11. If you were to write a Valentine’s Day card to your job, what would it say?
12. What’s the best love-related quote that applies to teamwork?
13. Who in the office would win “most likely to give the best Valentine’s gift”?
14. If the office had a Valentine’s Day mascot, what would it be?
15. What’s your favorite romantic movie or book and why?
16. What color best represents Valentine’s Day in your opinion: red, pink, or something else?
17. Would you rather get chocolate or flowers as an appreciation gift at work?
18. What’s the funniest Valentine’s Day tradition you’ve ever heard of?
19. If you had to create a Valentine’s Day-themed product for work, what would it be?
20. What’s a “workplace love language” (like acts of service, words of affirmation) that makes your job easier?

Dating Related Valentine’s Day Questions to Ask Your Employees or Team for Deep Conversation

1. What’s one thing you admire most about your partner or someone you love?
2. What’s the most important lesson you’ve learned from past relationships?
3. How do you define love in one sentence?
4. What’s the best way to support a partner or loved one during a tough time?
5. What’s your favorite memory of a romantic gesture (big or small)?
6. How has your perspective on love changed over the years?
7. What’s the most meaningful compliment you’ve ever received from someone?
8. Do you think love is more about timing or effort? Why?
9. What’s one quality you think is essential in any healthy relationship?
10. What’s the most unique date idea you’ve ever had or experienced?
11. Has a partner ever surprised you on Valentine’s Day? What happened?
12. What’s a romantic tradition you’d love to try or create?
13. How do you show love to others in non-traditional ways?
14. What’s your favorite memory of falling in love or connecting with someone?
15. Do you believe love can be expressed without words? How?
16. What role does humor play in your relationships?
17. What’s a piece of advice you’d give to someone about love or dating?
18. Do you think people can fall in love at first sight? Why or why not?
19. What’s something romantic you’ve always wanted to do but haven’t yet?
20. How do you balance work, life, and love in your daily routine?

Valentine’s Day-Themed Funny and Hilarious Questions to Ask Your Coworkers

1. If Cupid worked in our office, what would his job title be?
2. What’s the worst Valentine’s Day candy you’ve ever tried?
3. If love were a KPI, what would your office’s performance rating be?
4. Which office supply would make the most awkward Valentine’s gift?
5. If you had to send a Valentine’s card to your boss, what would it say?
6. What’s the funniest romantic fail you’ve ever witnessed?
7. If our office had a Valentine’s Day dance, who’d win the award for best moves?
8. What’s the most ridiculous Valentine-related email subject line you can think of?
9. If our office printer fell in love with the stapler, what would their love story be called?
10. Which romantic movie best describes our team dynamics?
11. If someone brought heart-shaped donuts to the office, who’d eat the most?
12. What’s the cheesiest Valentine’s Day pun you’ve ever heard?
13. If you had to write a Valentine’s Day poem for your favorite coworker, how would it start?
14. Who would be most likely to secretly eat all the Valentine’s chocolates in the breakroom?
15. If our office had a Valentine’s Day mascot, what embarrassing costume would they wear?
16. What’s the funniest Valentine’s Day email you could send the whole team?
17. If someone sent a singing Valentine to the office, who’d be the most embarrassed?
18. Which office tool would write the best romantic novel?
19. If Valentine’s Day had a dress code, what silly rule would you add?
20. What’s one thing you’d never want to see in a Valentine’s Day office gift exchange?

Workplace Valentine’s Day Would You Rather

1. Would you rather receive a giant teddy bear or a bouquet of staplers?
2. Would you rather write a romantic email to the whole team or serenade your boss?
3. Would you rather eat only Valentine’s candy at work for a week or write 50 Valentine cards?
4. Would you rather decorate your desk with hearts or dress like Cupid all day?
5. Would you rather share a box of chocolates or a box of office supplies?
6. Would you rather get flowers from a secret admirer or know who sent them?
7. Would you rather organize a Valentine’s Day office party or clean up after it?
8. Would you rather eat conversation hearts or heart-shaped donuts every day?
9. Would you rather wear a pink suit to work or a red one?
10. Would you rather have a Valentine’s potluck or a Valentine’s dessert competition?
11. Would you rather give a Valentine’s speech or perform a Valentine’s skit?
12. Would you rather have a surprise Valentine’s Day meeting or a surprise Valentine’s Day gift?
13. Would you rather send anonymous Valentines to the whole team or write one heartfelt card?
14. Would you rather receive a mystery Valentine or no Valentine at all?
15. Would you rather work on Valentine’s Day or have mandatory time off?
16. Would you rather drink Valentine’s-themed coffee or eat Valentine’s-themed lunch?
17. Would you rather send love-themed memes to the office or decorate everyone’s desk?
18. Would you rather give a Valentine to your boss or your least favorite coworker?
19. Would you rather receive chocolates shaped like hearts or shaped like office supplies?
20. Would you rather have a Valentine’s Day karaoke contest or a dance-off?

Office-Themed Valentine’s Day Never Have I Ever

1. Never have I ever sent a Valentine’s Day card to a coworker.
2. Never have I ever eaten someone else’s Valentine’s candy in the breakroom.
3. Never have I ever accidentally sent a romantic email or message to the wrong person.
4. Never have I ever secretly re-gifted a Valentine’s Day present.
5. Never have I ever decorated my desk for Valentine’s Day.
6. Never have I ever had a workplace crush.
7. Never have I ever accidentally spilled coffee on a Valentine’s Day card or gift.
8. Never have I ever bought Valentine’s candy just because it was on sale.
9. Never have I ever planned a surprise Valentine’s Day activity for a coworker.
10. Never have I ever been embarrassed by a Valentine’s Day gift at work.
11. Never have I ever received a secret Valentine in the office.
12. Never have I ever forgotten Valentine’s Day until someone reminded me.
13. Never have I ever used Valentine’s Day as an excuse to leave work early.
14. Never have I ever made a Valentine’s Day pun in a meeting.
15. Never have I ever eaten Valentine’s candy that wasn’t mine.
16. Never have I ever accidentally thrown away someone’s Valentine’s gift.
17. Never have I ever received flowers or chocolates at work.
18. Never have I ever spilled the beans about someone’s secret Valentine gift.
19. Never have I ever participated in a Valentine’s Day office gift exchange.
20. Never have I ever bought a last-minute Valentine’s Day gift on my lunch break.

Workplace Couples Valentine’s Day Truth or Dare

Truths:

1. Have you ever helped a coworker plan a romantic Valentine’s surprise?
2. What’s the most romantic thing you’ve ever done for someone?
3. If you had to write a Valentine’s card to your boss, what would it say?
4. What’s the most awkward Valentine’s Day moment you’ve had at work?
5. Have you ever regifted a Valentine’s Day present?
6. What’s your favorite Valentine’s Day memory?
7. If you could plan a dream Valentine’s Day for someone, what would it be?
8. What’s a love-related movie or song you secretly enjoy?
9. Who in the office would give the funniest Valentine’s gift?
10. What’s the worst Valentine’s candy you’ve ever eaten?

Dares:

1. Create a cheesy Valentine’s Day pun about work and share it with the group.
2. Write a fake Valentine’s card to the office printer and read it out loud.
3. Sing a romantic song with office-themed lyrics.
4. Share your go-to pickup line with the team.
5. Draw a Valentine’s Day doodle and show it to your coworkers.
6. Compliment every coworker in the room using a Valentine’s theme.
7. Pretend to propose to one of your coworkers using a stapler as a ring.
8. Share your funniest Valentine’s Day story in 30 seconds.
9. Write a Valentine’s haiku about your favorite office snack.
10. Act out Cupid shooting arrows at coworkers for 30 seconds.

Valentine’s Day Trivia for Work

1. What Roman god is associated with Valentine’s Day? (Answer: Cupid)
2. When was Valentine’s Day officially recognized as a holiday? (Answer: 496 AD)
3. What flower is most commonly associated with Valentine’s Day? (Answer: Red rose)
4. Which country started the tradition of Valentine’s cards? (Answer: England)
5. What candy was originally called “Chicken Feed”? (Answer: Candy Corn)
6. How many Valentine’s Day cards are exchanged each year worldwide? (Answer: About 1 billion)
7. What city is known as the “City of Love”? (Answer: Paris)
8. What is the most popular Valentine’s Day gift? (Answer: Chocolate)
9. What percentage of Valentine’s Day flowers are bought by men? (Answer: About 73%)
10. Which Valentine’s Day candy takes the longest to make? (Answer: Conversation hearts)
11. What is the most popular proposal day of the year? (Answer: Valentine’s Day)
12. What does the “X” in “XOXO” stand for? (Answer: Kiss)
13. What color rose is traditionally given for friendship? (Answer: Yellow)
14. How many conversation hearts are made each year? (Answer: About 8 billion)
15. What country celebrates Valentine’s Day by giving wooden spoons? (Answer: Wales)
16. What is the name of the Valentine’s Day mascot in Japan? (Answer: Kanji Cupid)
17. Which U.S. state produces most of the country’s roses? (Answer: California)
18. What’s the most expensive Valentine’s Day gift ever given? (Answer: The Taj Mahal)
19. What holiday falls exactly one day after Valentine’s Day? (Answer: Singles Awareness Day)
20. How long does it take for a conversation heart to dissolve in water? (Answer: About 5 minutes)

Valentine’s Day Riddles for Work

1. I’m sweet and often come in a box, but I’m not a tool for fixing socks. What am I? (Answer: Chocolates)
2. I can be “red,” “white,” or “blush,” and I’m often poured to celebrate love. What am I? (Answer: Wine)
3. I’m sharp but not mean, I hold things together but can’t be seen. What am I? (Answer: Stapler)
4. I’m a symbol of love, but I’m not alive. I’m sometimes made of paper or metal to survive. What am I? (Answer: A heart)
5. I fly without wings, I shoot without a gun, and I’m known for spreading love to everyone. What am I? (Answer: Cupid’s arrow)
6. I’m round and sweet with frosting on top, I’m a treat for Valentine’s Day that’s hard to stop. What am I? (Answer: A donut)
7. I’m a plant that says “I love you,” but I have thorns that can prick you too. What am I? (Answer: A rose)
8. I’m small, colorful, and have words to say, I’m a treat you might eat on Valentine’s Day. What am I? (Answer: Conversation hearts)
9. I rhyme with “dove” and symbolize care, I’m what you feel when someone is there. What am I? (Answer: Love)
10. I’m a piece of paper that you give with glee, filled with kind words and sent secretly. What am I? (Answer: A Valentine’s card)

Valentine’s Day Quiz for Workplace

1. What is the most popular Valentine’s Day gift in the workplace? (Answer: Chocolates or candy)
2. Which famous playwright wrote the line “If music be the food of love, play on”? (Answer: William Shakespeare)
3. Which ancient civilization started the tradition of giving roses? (Answer: Romans)
4. What day is referred to as “Galentine’s Day”? (Answer: February 13th)
5. What is the most popular Valentine’s Day flower in the U.S.? (Answer: Red roses)
6. How much money does the average American spend on Valentine’s Day? (Answer: Around $165)
7. Which candy company produces the most conversation hearts? (Answer: NECCO)
8. What is the meaning of a pink rose on Valentine’s Day? (Answer: Gratitude and admiration)
9. Which bird is often associated with love and Valentine’s Day? (Answer: Dove)
10. Who is the patron saint of Valentine’s Day? (Answer: Saint Valentine)
11. What country celebrates Valentine’s Day by giving chocolate exclusively to men? (Answer: Japan)
12. What is the oldest Valentine’s Day card still in existence? (Answer: A card from 1415, housed in the British Museum)
13. What is the most popular Valentine’s Day movie genre? (Answer: Romantic comedy)
14. How many roses are sold worldwide on Valentine’s Day? (Answer: About 250 million)
15. What’s the most popular Valentine’s Day emoji? (Answer: Heart emoji ❤️)
16. Which fictional couple is known for their tragic love story? (Answer: Romeo and Juliet)
17. What is the Greek word for romantic or passionate love? (Answer: Eros)
18. In which century did Valentine’s Day cards become mass-produced? (Answer: 19th century)
19. What’s the busiest restaurant day of the year? (Answer: Valentine’s Day)
20. Which country has a tradition of “Friendship Day” instead of Valentine’s? (Answer: Finland)

Conclusion

Valentine’s Day icebreaker questions are an excellent way to foster connection, build relationships, and add a touch of fun to your workplace. Whether you’re seeking deep conversations, light-hearted laughter, or friendly competition, these activities can help break the monotony and create lasting memories within your team. By incorporating these creative and inclusive questions into your office celebrations, you not only celebrate the season of love but also strengthen the bonds within your workplace, making it a more enjoyable and productive environment.

Remember, the key is to keep things respectful, light, and fun—ensuring everyone feels comfortable and included. So go ahead, inject some joy into your Valentine’s Day office activities with these icebreaker ideas, and make this special day an opportunity for team building and shared laughter!