100 Valentine's Day would you rather questions for work
Work-safe would you rather questions about chocolate, cards, kindness and the office, with no dating or romance. Read them out, screen-share the deck, or post one a day in chat.
Valentine's Day would you rather questions for work give coworkers two fun choices, like a hot chocolate bar or a cookie table, so everyone can answer without talking about their love life. Below are 100 of them in five sets: sweet treats, cards and kindness, funny picks, the office, and quick picks for a chat poll. Six to eight fill a 10-minute meeting opener.
Chocolate and sweet treat would you rather questions
The easiest place to start: everyone has a strong opinion about chocolate, and nobody has to share anything personal.
1. Would you rather get a box of chocolates with a flavor map or a box where every piece is a surprise?
2. Would you rather eat only dark chocolate or only white chocolate for the rest of February?
3. Would you rather have a hot chocolate bar at the office or a cookie decorating table?
4. Would you rather bite into a chocolate and find caramel or find a cherry?
5. Would you rather bake heart-shaped cookies for the team or decorate one big cake for everyone?
6. Would you rather share a giant chocolate chip cookie with the team or get your own tiny cupcake?
7. Would you rather have candy hearts that print what you are thinking or candy hearts that give you advice?
8. Would you rather your desk drawer refill with chocolate every Monday or your coffee always stay the perfect temperature?
9. Would you rather taste-test every chocolate in a factory for a day or design a brand new candy bar?
10. Would you rather make a hot chocolate bomb on camera or watch someone else try it first?
11. Would you rather have a pink frosted donut or a red velvet cupcake?
12. Would you rather eat a dessert that looks perfect and tastes plain or one that looks like a mess and tastes amazing?
13. Would you rather take the last chocolate in the box or give it away and get the credit?
14. Would you rather have marshmallows in everything or sprinkles on everything?
15. Would you rather have a chocolate fountain in the break room or a candy wall in the lobby?
16. Would you rather eat only heart-shaped snacks or only snacks shaped like your initials?
17. Would you rather swap snack drawers with a coworker for a week or pick the snacks for the whole office for a month?
18. Would you rather get a box of candy hearts that all say nice work or a chocolate bar with your name on the wrapper?
19. Would you rather judge the team bake-off or enter it?
20. Would you rather top your hot chocolate with whipped cream or stir it with a peppermint stick?
Want the chocolate for real? In a hot chocolate bomb workshop, a kit ships to every guest and a live host shows the team how to make them on camera.
Want a Valentine's event someone else runs?
Questions fill ten minutes. For a full hour that remote and office guests share, a live host runs a workshop or game while you just join. With a kit, the same chocolate or candle supplies land on every desk, so nobody has anything to prep. Prices below are live for your group size.
Hot Chocolate BombStarting at $90 USD / person
Candle MakingStarting at $84 USD / person
Gratitude Games & GrinsStarting at $39 USD / person
Hosted games book about 2 weeks ahead. Kit workshops need about 3 weeks for US addresses, or about 5 weeks with guests in Canada or abroad. Reserve online with a 50% deposit, or send your date and get a full plan within 24 hours. See every option on our virtual Valentine's Day party page.
Get a free quoteWould you rather questions about cards, thanks and kindness
Valentine's Day at work is really about appreciation. These get people talking about how they like to give and get thanks.
21. Would you rather write a thank-you card to every teammate or get one thank-you card from everyone?
22. Would you rather get a handwritten note or a shout-out in the team meeting?
23. Would you rather decorate a card with glitter or with stickers only?
24. Would you rather give compliments that rhyme for a day or compliments in a movie trailer voice?
25. Would you rather leave secret kind notes on desks or be the one who finds them?
26. Would you rather have your best idea of the year written up in a card or framed on the wall?
27. Would you rather send a thank-you card to a coworker from your first job or to a teacher who helped you?
28. Would you rather get a kudos board full of sticky notes or one long, thoughtful letter?
29. Would you rather be known for giving the best cards or bringing the best snacks?
30. Would you rather help a teammate finish a project or cover their meeting so they can leave early?
31. Would you rather be thanked in front of the whole team or in a quiet one-on-one?
32. Would you rather get a small treat every week or one big surprise once a year?
33. Would you rather start a pay-it-forward coffee chain at work or a pay-it-forward cookie chain?
34. Would you rather write a haiku for a coworker or draw them a quick portrait?
35. Would you rather get a friendship bracelet from your team or a framed team photo?
36. Would you rather have a day when everyone says yes to your ideas or a day when everyone brings you snacks?
37. Would you rather pick a kudos award for your manager or let your team pick one for you?
38. Would you rather be the person who remembers every birthday or the one who plans every celebration?
39. Would you rather get a handmade candle or a handmade mug?
40. Would you rather say thank you with a song or with one dance move?
Turn the thank-you questions into the real thing: a hosted card making class ships card supplies to each guest, and everyone ends the hour with a card for a coworker.
Funny Valentine's Day would you rather questions
Silly choices where both sides are a little ridiculous. Good for a party or the last five minutes before a long weekend.
41. Would you rather have Cupid as your desk neighbor or a talking teddy bear as your assistant?
42. Would you rather have every email you send end with a heart emoji or every meeting invite play soft harp music?
43. Would you rather leave a trail of glitter wherever you walk or have tiny hearts float over your head when you are happy?
44. Would you rather have a pet that only eats candy hearts or a houseplant that sings when you water it?
45. Would you rather wear red every day in February or pink every day in March?
46. Would you rather have every pen in the office topped with a fluffy heart or every office chair turned pink?
47. Would you rather sit on a giant teddy bear desk chair or a beanbag shaped like a heart?
48. Would you rather have your laptop type only in red or only in fancy cursive?
49. Would you rather get a singing card that never stops or a pop-up card that is ten feet tall?
50. Would you rather find a paper valentine in your mailbox every day or one paper valentine the size of a door?
51. Would you rather be a Cupid with terrible aim or a mail carrier who delivers every card one day late?
52. Would you rather speak only in candy heart phrases for a day or only in greeting card rhymes?
53. Would you rather have your video background fill with falling hearts or your voice gain a dramatic echo?
54. Would you rather have flowers that bloom whenever someone laughs or chocolate that never melts?
55. Would you rather get a card from your future self or send one to your past self?
56. Would you rather have a dog that delivers notes around the office or a cat that reviews everyone's cards?
57. Would you rather decorate the office with 1,000 paper hearts or one giant balloon arch?
58. Would you rather spend a night in a candy store or a night in a flower shop?
59. Would you rather have teddy bears do your filing or a robot write all your thank-you notes?
60. Would you rather have a kazoo ringtone or a ringtone of a choir singing your name?
Valentine's Day would you rather questions for the office
Questions about the team, the office and the week itself. These double as quiet planning research for your next event.
61. Would you rather plan the office Valentine's party or be a guest with zero jobs?
62. Would you rather have a team potluck of only desserts or only snacks that are red or pink?
63. Would you rather trade lunch orders with a teammate for a day or trade video backgrounds for a week?
64. Would you rather spend Valentine's week on a team volunteer day or a team workshop?
65. Would you rather make candles with the team or make hot chocolate bombs with the team?
66. Would you rather have a silly team photo or a nice one?
67. Would you rather run a meeting from a heart-shaped agenda or end every meeting with a compliment round?
68. Would you rather get the Friday before Valentine's Day off or leave an hour early every Friday in February?
69. Would you rather send the team a card or a shared playlist?
70. Would you rather get a desk plant from the team or a mug with a team inside joke on it?
71. Would you rather be on the decorations committee or the snacks committee?
72. Would you rather do a candy swap or a book swap?
73. Would you rather present your next update with a Cupid emoji on every slide or with a soundtrack?
74. Would you rather have a team lunch or a team dessert break?
75. Would you rather have a kudos channel in chat or a kudos wall in the office?
76. Would you rather write the team's Valentine's card to a client or design it?
77. Would you rather sit next to a coworker who always brings treats or one who always brings good news?
78. Would you rather get paired with a random coworker for coffee each week or join one big team lunch each month?
79. Would you rather celebrate with a long team lunch or a short afternoon break with treats?
80. Would you rather pick a team charity for February or a team goal for February?
Quick Valentine's would you rather questions for a chat poll
Short two-word picks for a chat poll, a stand-up or a slide everyone votes on with a thumbs up.
81. Would you rather get tulips or a potted cactus?
82. Would you rather have chocolate or gummy candy?
83. Would you rather get a card or a phone call?
84. Would you rather wear red or pink?
85. Would you rather have cookies or cupcakes?
86. Would you rather get chocolate truffles or chocolate bark?
87. Would you rather draw hearts or stars?
88. Would you rather use glitter or stickers?
89. Would you rather get a poem or a playlist?
90. Would you rather sip hot cocoa or a peppermint latte?
91. Would you rather color with crayons or markers?
92. Would you rather get a teddy bear or a houseplant?
93. Would you rather have pancakes or waffles?
94. Would you rather watch a comedy or an animated movie?
95. Would you rather get a candle or a mug?
96. Would you rather eat strawberries or cherries?
97. Would you rather write in cursive or in all capitals?
98. Would you rather get a kind text or a kind email?
99. Would you rather pick caramel or peanut butter?
100. Would you rather be a thank-you card or a sticky note?
How to play would you rather at work
Share the deck below on a call, or read from the lists above. Four steps turn a list into a game.
Chocolate and sweet treatsWould you rather get a box of chocolates with a flavor map or a box where every piece is a surprise?
- Pick one set. Sweet treats or quick picks for a first round, kindness or office questions once people are warm.
- Read it, then vote at once. Hands up, one or two fingers on camera, or a chat poll. Everyone answers before anyone explains.
- One defender per side. Ask one person from each side for a single sentence on why. That is where the laughs are.
- Quit while people want more. Six to eight questions fill about 10 minutes. Save the rest for the next meeting.
In the office, hybrid, on video or in chat
- In the office: read the question out, then point left for the first choice and right for the second. People move to that side of the room.
- Hybrid: put the deck on the shared screen so the room and the remote faces see the same card, and let a remote person read each one.
- On a video call: share the deck above, vote with one or two fingers on camera, and ask the smaller side to defend their pick.
- In chat: post one question a day in Valentine's week with two emoji reactions to vote, then share the closest result on Friday.
Keep Valentine's Day comfortable for everyone
Every question on this page follows these rules. Use them for any you add.
- Keep it about friendship, thanks and treats. No questions about dates, crushes, partners or anyone's home life.
- Make it a choice, never a confession. Every question here can be answered in one word.
- Not everyone celebrates Valentine's Day, so frame it as a February treat break that anyone can join.
- Let people pass. A quiet vote counts as playing.
- Skip alcohol pressure. Treats, cocoa and coffee work for everyone.
Sending something instead of meeting up? Our Valentine's Day gifts for coworkers and clients are chocolate boxes and towers.
