These Valentine’s Day Would You Rather questions are perfect for kids and families—easy, fun conversation starters for dinner, parties, or game night.
Valentine’s Day doesn’t have to mean big plans or extra stress. Sometimes the best memories come from laughing around the table, asking silly questions, and just being together.
These Valentine’s Day Would You Rather questions are one of my favorite easy ways to spark conversation with kids, teens, and even adults—no prep, no pressure, just fun connection.
They’re perfect for dinner time, classroom parties, family game night, or even a quick car ride conversation.
Looking for more question games? Visit our Icebreaker Questions for Kids hub for easy, fun ways to get kids talking.
Why We Love Valentine’s Day Would You Rather Questions
This game works so well because it’s:
- Easy for all ages to play
- Great for shy kids who don’t love open-ended questions
- Silly, lighthearted, and conversation-starting
- Completely screen-free
- Perfect for busy parents who want connection without planning
Sometimes the simplest games bring the biggest smiles.
How to Play Valentine’s Day Would You Rather
You can play this game however it fits your family:
- Take turns asking one question at a time
- Let everyone answer (no wrong answers!)
- Ask follow-up questions like “Why did you choose that?”
- Use them at the dinner table, in the classroom, or during a party
- Print them out or just read them from your phone
No rules. No winners. Just conversation and laughs.
The Best Valentine’s Would You Rather Questions
Grab our printable Valentine’s Day Would You Rather Questions right here, or use the list of questions below.
- Would you rather drink love potion to make someone fall in love with you or shoot two people with arrows to make them fall in love?
- Would you rather receive chocolates or candy hearts?
- Would you rather watch the Notebook every day for the rest of your life or The Proposal?
- Would you rather give a hug or a kiss?
- Would you rather go on a fancy expensive date or do a romantic night at home?
- Would you rather make or buy a Valentine’s Day card?
- Would you rather eat a pound of chocolate in one sitting or write 500 valentines in one sitting?
- Would you rather give your teacher a Valentine or give your friend a Valentine?
- Would you rather get 10 dozen roses for Valentine’s Day or 10 pounds of chocolate?
- Would you rather make a secret handshake or make a silly dance?
- Would you rather go out dancing until midnight or watch a chick flick marathon?
- Would you rather eat a piece of candy off the floor or eat a piece of candy after a dog licked it?
- Would you rather get a couple’s massage on the beach or hang out in a hot tub on top of a mountain?
- Would you rather be at a Valentine’s Day party or at a winter party?
- Would you rather skip Valentine’s Day or skip New Year’s Eve?
- Would you rather attend a music class or an art class?
- Would you rather celebrate Galentine’s Day or celebrate Valentine’s Day?
- Would you rather go on a date to take dance lessons or go to a cooking class?
- Would you rather play videos games or board games?
- Would you rather have warm chocolate lava cake for dessert or crème Brulee with strawberries?
- Would you rather build a tent or build with legos?
- Would you rather live in a romantic comedy or a superhero movie?
- Would you rather play inside or outside?
- Would you rather be a part of the cast of the Office or part of the cast of Gray’s Anatomy?
- Would you rather eat flower petals or eat a heart-shaped dog treat?
- Would you rather spend a weekend in Paris, the city of love, or Philadelphia, the city of Brotherly Love?
- Would you rather have bright pink hair or a bright red nose?
- Would you rather be serenaded by one of the Jonas Brothers or by Ed Sheeran?
- Would you rather create a love potion or use Cupid’s bow and arrows to spread the love?
- Would you rather eat a dozen chocolate-covered strawberries or three whole candied apples?
- Would you rather give your friends homemade Valentines or store-bought Valentines?
- Would you rather be proposed to in front of a huge crowd of people or alone in a room full of candles?
- Would you rather eat a heart-shaped cupcake or a Cupid-shaped cookie?
- Would you rather cuddle in bed with a puppy or with your significant other?
- Would you rather give your teacher chocolate or flowers on Valentine’s Day?
- Would you rather date Mickey Mouse or Pluto?
- Would you rather only be able to wear red clothes, pink clothes or white clothes for the next year?
- Would you rather kiss Iron-Man or Spiderman?
- Would you rather get a lot of valentines from people you don’t know very well or get just one from someone who is special to you?
- Would you rather eat chocolate-covered crickets or candied worms (actual worms)?
- Would you rather have bright red skin or have your heartbeat loud enough for everyone in the room to hear it?
- Would you rather in fall love with Quasimodo or with an unchangeable beast?
- Would you rather host a Valentine’s Day party or be a guest at a Valentine’s Day party?
- Would you rather have been on the Titanic or taken a Walk to Remember?
- Would you rather attempt to do the Dirty Dancing lift or the final dance in Step-Up?
- Would you rather get to write the script for the Valentine’s episode of your favorite TV show or get to be in the Valentine’s episode of your favorite TV show?
- Would you rather rewatch the entire Twilight series or rewatch all of The Hunger Games?
- Would you rather spend Valentine’s Day with your family or spend Valentine’s Day with your friends?
- Would you rather be a star in Breakfast Club or My Best Friend’s Wedding?
- Would you rather get Valentine’s candy from your teacher or get a homework pass from your teacher?
- Would you rather be Cosette from Les Miserables or Christine from Phantom of the Opera?
- Would you rather go to a Valentine’s Day party with really good food but not much else to do or go to a Valentine’s Day party with no food, but with really fun games and activities?
- Would you rather wear pink every Wednesday for the rest of your life or eat fat-filled protein bars for breakfast every day?
- Would you rather attend a Valentine’s Day party at school or attend a Valentine’s Day party at someone’s house?
- Would you rather kiss someone with bad breath or eat escargot?
- Would you rather eat only red foods on Valentine’s Day or eat only white foods on Valentine’s Day?
- Would you rather go to a spa resort for an entire day or spend the day at Magic Kingdom?
- Would you rather have a class Valentine’s Day party or have no homework for a week?
- Would you rather receive a personalized I love you book or receive a book of Valentine’s Day coupons?
- Would you rather receive a mushy valentine or receive a funny valentine?
- Would you rather hold hands with someone during a movie or have someone’s arm around your shoulder during a movie?
- Would you rather write a Valentine’s Day poem that you read to the whole school at a special assembly or design a Valentine’s Day poster that is displayed in the school office?
- Would you rather marry your best friend when you turn 40 even if they’re not attractive or marry someone who is attractive but regularly rude to others?
- Would you rather receive 100 roses or receive 100 pieces of chocolate?
- Would you rather fall in love with a wedding singer or with someone who has short-term memory loss?
- Would you rather give valentines to all of the boys in your class or give valentines to all of the girls in your class?
- Would you rather fall in love at first sight or fall in love over years of friendship?
- Would you rather have to always write with a red pen or pencil for the rest of your life or have to dot all of your “i”s and “j”s with hearts for the rest of your life?
- Would you rather read a Nicholas Sparks book or a Jane Austen one?
- Would you rather get a Valentine’s Day kiss from a big, slobbery dog or get a Valentine’s Day kiss from a camel?
- Would you rather recreate your first date with your significant other or do something totally new for Valentine’s Day?
- Would you rather have pink hair or purple eyes?
- Would you rather receive a mailbox full of love letters or be serenaded with an original song?
- Would you rather give out chocolate kisses or real hugs for 10 days?
- Would you rather have Aphrodite’s love or her beauty?
- Would you rather have flowers grow in your footsteps or helium balloons released when you sit down?
- Would you rather act in a production of Romeo & Juliet or act and sing in a production of Grease?
- Would you rather light 1,000 candles or pick 1,000 roses?
- Would you rather go on a gondola ride in Venice or a hot air balloon ride over Napa Valley?
- Would you rather only eat foods that are red or only foods that are white?
- Would you rather watch a sunset in Santorini, Greece, or a sunrise in Sydney, Australia?
- Would you rather receive perfume, or cologne, or flowers?
- Would you rather only kiss only person ever in your life or never be in a real relationship?
- Would you rather shoot Cupid’s bow or be shot by Cupid’s bow?
- Would you rather get a handwritten personal card for a Valentine or a dozen of your favorite flowers?
- Would you rather get 1,000 Valentines from friends or 1 from your secret crush?
- Would you rather kiss a frog or snuggle with a snake?
- Would you rather receive a dozen red roses or 12 chocolate doughnuts?
- Would you rather be a matchmaker or have a matchmaker match you with the perfect person?
- Would you rather dress up as Cupid or dress up as the Easter bunny?
- Would you rather get a huge teddy bear or a huge box of chocolates?
- Would you rather tell your crush you like them or solve 100 Math problems?
- Would you rather have a dole of doves or a tank full of lobsters loose in your house for a day?
- Would you rather get an expensive give or go on vacation?
- Would you rather have someone build you your dream house or do anything you wish for a year?
- Would you rather laugh uncontrollably whenever Valentine’s Day is mentioned or burst into tears?
- Would you rather have a secret admirer or be the secret admirer?
- Would you rather eat sweet candy or sour candy?
- Would you rather write and read a Valentine’s Day poem to a large crowd or sing and dance your favorite song to the same crowd?
When to Use These Questions
These work great for:
- Valentine’s Day dinner
- Classroom parties
- Family game night
- Road trips
- Morning meeting or circle time
- A calm bedtime conversation
They’re flexible, quick, and always fun.
More Valentine’s Day Printables You’ll Love
If you’re planning more Valentine fun, check these out next:
- Valentine’s Day This or That Questions
- Valentine’s Day Scattergories Free Printable
- Valentine’s Day Color By Number Sheets
- Valentine’s Day Journal Prompts for Kids
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Michele Tripple is a renowned author and expert in the fields of parenting, relationships, and personal development. She is a certified Life Coach with her degree in marriage and family studies, her experience as a Family Life Educator, and over a decade of experience as a professional writer; Michele has authored books that provide practical advice and insights into improving family dynamics and personal growth. Her work is celebrated for its blend of research-driven information and relatable, real-world applications. Michele has been a keynote speaker at conferences and has contributed to numerous publications and media outlets, solidifying her reputation as an authoritative voice in her field and helping families build relationships.