Valentine’s Day Questions
School card swaps, candy-heart puns and plans for next February, one card at a time.
- Time
- 15–45 min
- Players
- Two players, no turns
- Best for
- February 14, over dinner or dessert
- Deck
- 75 questions in 5 categories
How to use these Valentine’s Day questions
- Pick a category from the menu under the card, or keep “All categories”.
- Read the question on the top card aloud and both answer it.
- Swipe the card away, or tap “Next question”, for the next one. Questions do not repeat until you have seen the whole category.
- Tap the heart to save a question on this device, or tap “Make a 10-question list” for a list you can copy.
When to ask Valentine’s Day questions
Valentine’s Day usually comes with a plan for where to go and none at all for what to talk about. A few questions fill the gaps between courses and keep the evening about the two of you rather than the menu.
Waiting for the food
Funny and silly or Valentine’s past, light enough to answer between bites of bread.
Over dessert
Sweet and romantic and Us so far, once the room quiets down and nobody is rushing you.
On the walk home
Save The year ahead for the cold walk back, when plans for next February feel easy to make.
Ways to use Valentine’s Day questions
One card per course
Keep the phone face down between courses and draw one card each time a plate arrives: Valentine’s past with the starter, Sweet and romantic with dessert.
Answers on a valentine
Each pick three cards and write your answers inside a card for the other. Swap the cards and read them aloud before you say anything else.
Light, then deep, then ahead
Start the evening with Funny and silly, move to Us so far once you are settled, and save The year ahead for the end of the night.
Small tips for Valentine’s night
- If a question about the past brings up a story you already know, ask for one detail you have never heard.
- Pass on any card you are not in the mood for. Skipping is always fine.
- Tap the heart on the answers you want to hear again next February.
All 75 Valentine’s Day questions by category
The complete list, grouped by category. The cards above draw from the same list, so you can read ahead here and play there.
Valentine’s past
Light memories of February 14ths gone by, from school card swaps to candy you waited all year for.
- Did your class swap valentines at school, and what kind of cards did you hand out?
- Which Valentine’s candy did you look forward to most when you were growing up?
- Did your family do anything special on February 14 when you were young?
- What’s the most elaborate valentine you ever made as a kid, and how did it turn out?
- Which Valentine’s Day of ours stands out most so far, and why that one?
- Did you ever get a valentine with no name on it, and did you work out who sent it?
- What’s the most memorable Valentine’s message you’ve ever read, on a card, a sign or a candy heart?
- Which Valentine’s movie, song or TV ad from years ago is still stuck in your head?
Show all 15 in Valentine’s pastShow fewer
- Which Valentine’s Day from before we met makes you laugh when you look back on it now?
- What’s the funniest Valentine’s gift you’ve ever seen someone give or get?
- Did you ever make a valentine for a parent, a teacher or a pet? Which one?
- Which Valentine’s tradition from your childhood would you like to bring back for the two of us?
- Have you ever spent February 14 doing something completely unromantic, and how was it?
- What’s the best Valentine’s Day you’ve ever spent with friends?
- When you were younger, how did you picture a grown-up Valentine’s Day?
Us so far
The two of you, seen through a Valentine’s card: small moments, inside jokes and what surprised you.
- What did our first Valentine’s Day together feel like, and what do you remember most about it?
- When did you first think of me as your valentine, even before either of us used the word?
- Which ordinary day of ours deserved a Valentine’s card more than February 14 ever did?
- What about us would surprise the person you were a year before we met?
- Which moment with me would you put on the front of a valentine?
- Which small habit of ours feels more romantic to you than any holiday?
- If you could write only one line about us inside a card, what would it say?
- Which of our inside jokes would make the best Valentine’s card?
Show all 15 in Us so farShow fewer
- Which photo of the two of us best shows who we are right now?
- What surprised you most about falling for me?
- Which of our dates would you show a stranger to explain what we’re like together?
- Which chore or errand do you secretly enjoy doing with me?
- What’s a tiny moment with me you’ve never mentioned but still think about?
- What did you expect dating me would be like, and what turned out better?
- Which gift from me, big or tiny, have you kept the longest?
Sweet and romantic
Flowers, handwritten cards and the kind of romance each of you secretly likes best.
- If you planned February 14 hour by hour, what would the first and the last hour be?
- Do you like your Valentine’s Day plans to be a surprise, or would you rather help choose them?
- Which flower would you choose for me, and what do you think it says about me?
- If you could print one candy heart just for me, what would it say?
- Which love story from a book or film feels closest to ours?
- What’s the most romantic thing about an ordinary weeknight with me?
- If you wrote me a love poem, which part of me would get the first line?
- Do you like a valentine handwritten, store-bought or sung, and which have you liked most?
Show all 15 in Sweet and romanticShow fewer
- What’s one romantic cliché you secretly love?
- If you could keep only one moment from today, which would it be?
- If our love had a smell, a color and a sound, what would they be?
- What could a friend say about us that would make you blush?
- Where would you hide a valentine for me so I’d find it at the perfect moment?
- What do you hope I always remember about the way you love me?
- How would you like to be asked “Will you be my valentine?”
Funny and silly
Cupid, candy hearts and terrible puns, for when the evening needs a laugh.
- If Cupid hired you for one day, what would go wrong first?
- Which candy heart message best describes your mood today?
- What would our celebrity couple name be, and would it fit on a T-shirt?
- If you had to give a valentine to a kitchen appliance, which one would win your heart?
- What’s the most ridiculous Valentine’s gift you can imagine, and would you secretly love it?
- Which pun would you write on a valentine for me: “olive you”, “you’re grape” or one of your own?
- If you could only speak in love-song lyrics tonight, which line would you start with?
- Which cartoon pair are we most like before our morning coffee?
Show all 15 in Funny and sillyShow fewer
- If Valentine’s Day needed a new mascot instead of Cupid, what should it be?
- Where would you put a giant teddy bear if I gave you one?
- Rank these from least to most romantic: a single rose, a heart-shaped pizza, a love song on the kazoo.
- If we wrote a cheesy romance novel about ourselves, what would the title be?
- In a box of chocolates, would you be the caramel, the nut cluster or the mystery one?
- What’s the worst pickup line you could use on me tonight? Try it.
- If love were an Olympic sport, which event would the two of us win?
The year ahead
Small plans and hopes for the months between this Valentine’s Day and the next.
- Before the next box of candy hearts hits the shops, what’s one thing you’d like us to have done together?
- If next February 14 could be anywhere at all, what would the view be?
- What’s one small way we could feel like valentines on an ordinary Monday this year?
- What would you like to learn about me between now and next February?
- Which kind of date should we try this year that neither of us has ever been on?
- If we wrote a valentine to ourselves to open a year from now, what would it say?
- Which of our friends should we invite on a double date this year?
- What would make next Valentine’s Day even better than this one?
Show all 15 in The year aheadShow fewer
- What’s a dream for the two of us you’d like to say out loud this year?
- Which trip, big or small, should we plan before next February?
- What’s one thing about us you want to keep exactly the same this year?
- How could we make the most of the long, gray weeks after Valentine’s Day?
- Which skill could we learn together this year, like a dance or a language?
- What should we do more of this year, and what could we happily do less of?
- How should we celebrate the small wins this year, yours and mine?
Frequently asked questions
How many Valentine’s Day questions are there?
There are 75 questions, 15 in each of five categories: Valentine’s past, us so far, sweet and romantic, funny and silly, and the year ahead. The cards and the list on this page use the same set.
Do these work for a first Valentine’s Day together?
Yes. Sweet and romantic and Funny and silly need no shared history at all. A few cards, like the one about your first Valentine’s Day together, assume you have had one already, so skip those for now.
What should we do on Valentine’s Day besides talk?
Pick a plan from Valentine’s Day date ideas, from a night out without the crowds to ideas for long distance, then bring these questions along.
Can we play if we are apart on the 14th?
Yes. Read the cards to each other over a video call, or share a code on the long distance games page to play other games on two phones in the same order.