The oldest surviving valentine was written from a prison cell. Charles, Duke of Orleans, sent it to his wife in 1415 while locked up in the Tower of London after the Battle of Agincourt. It’s still there, in the British Library, and it refers to her as his “very gentle Valentine.” Something about that has always stayed with me. The holiday we associate with stuffed bears and chalky candy hearts started with a man writing love letters he wasn’t sure anyone would read. That tension between sincerity and performance runs through the entire history of February 14th, and it makes for trivia questions that hit differently than you’d expect.
I’ve run valentines day trivia at bars where couples showed up thinking they’d cruise through it, and at Galentine’s Day parties where the competition got genuinely vicious. The questions that work best aren’t the ones that test whether you memorized a Wikipedia page. They’re the ones that make half the room say one thing and the other half say another, both completely sure. That’s what I’ve tried to build here. A hundred questions that actually do something in a room.
1. The ancient Roman festival of Lupercalia, often cited as a precursor to Valentines Day, was celebrated on what date in February?
Everyone’s heard the Lupercalia connection. But I’ve watched tables argue about whether it was the 14th or a different day entirely. The festival involved priests running through the streets striking women with goat-hide thongs, which was somehow supposed to boost fertility. Romance has come a long way.
2. How many Saint Valentines does the Catholic Church actually recognize?
This is one of those questions where the answer makes the holiday feel stranger and more interesting than you thought it was. We talk about “Saint Valentine” like there was one guy. There wasn’t.
3. Which English poet is most often credited with first linking Valentines Day to romantic love in his writing?
This one separates people who’ve read about the holiday from people who’ve really read about it. The answer isn’t modern. It’s not even close to modern.
4. In what year was the oldest known valentine still in existence written?
I mentioned this in the intro, but in a trivia setting, people’s guesses span about four centuries. The range of confidence is beautiful.
5. The ancient Egyptians believed love and emotion originated not in the heart but in what organ?
I love opening a valentines set with this because it immediately tells the room this isn’t going to be the quiz they expected. Every table leans in.
6. Pope Gelasius declared February 14th as St. Valentine’s Day in what century?
Century questions are sneaky. People think they can narrow it down, and they usually overshoot by a few hundred years in either direction.
7. In medieval times, what did people believe happened on February 14th in the natural world that reinforced its connection to romance?
This is one of those questions where the answer is so specific and so charming that people remember it for years.
8. Approximately how many valentines are sent each year in the United States, making it the second-largest card-sending holiday?
The number is staggering. And the fact that it’s only second always gets a reaction.
9. What percentage of Valentines Day cards are purchased by women?
This one starts arguments. Real ones. I’ve seen couples turn to each other mid-question with looks that could curdle milk.
10. What was the first type of Valentines Day candy box shaped like a heart, and what company introduced it?
People know the shape. Almost nobody knows who made it first.
11. The conversation hearts made by the New England Confectionery Company (Necco) were originally based on what Civil War-era invention?
This is the kind of origin story that makes a candy you’ve eaten a thousand times suddenly feel like an artifact.
12. How much does the average American spend on Valentines Day gifts?
I usually give a range for this one. The number has climbed pretty dramatically in the last decade. People who haven’t bought a valentine in a few years always guess low.
13. What color roses supposedly signify friendship rather than romantic love?
Easy question. But I include it because it gives the room a win, and after some of these harder ones, they need it.
14. Roughly how many roses are produced for Valentines Day in the U.S. each year?
Give them a multiple choice: 50 million, 110 million, 250 million, or 500 million. Watch the room fracture.
15. What country produces most of the roses sold in the United States for Valentines Day?
People guess the Netherlands, and it’s a reasonable guess. But the supply chain for your February roses is a lot closer to the equator than most people think.
16. Sweethearts conversation hearts were off the market for an entire year after Necco went bankrupt. What year was that?
If you were alive and paying attention, you remember the panic. If you weren’t, this feels like a trick question.
17. What is the most popular Valentines Day gift in the United States, beating out flowers and chocolate?
This one always gets pushback. People are so locked into the flowers-and-chocolate narrative that the actual answer feels wrong even after you say it.
18. In Roman mythology, Cupid is the son of which goddess?
Straightforward, but it anchors the section. And about 30% of people mix up the Greek and Roman names, which is exactly what I want.
19. In the original Greek myths, Eros wasn’t a chubby baby. How was he typically depicted?
This is the question that makes Cupid interesting again. The cherub image is so dominant that people genuinely don’t believe the original version.
20. According to myth, Cupid carried two types of arrows. What did each type do?
People know about the gold ones. The second type is where it gets good.
21. In the famous myth, Cupid falls in love with a mortal woman. What is her name?
Classic myth, and it’s a good checkpoint question. If people know this, they’re tracking. If they don’t, the story itself is worth telling.
22. The word “cupidity” comes from the same Latin root as Cupid. What does it mean?
I love this one because it feels like it should mean something romantic and it absolutely doesn’t.
23. What 1989 romantic comedy, often replayed around Valentines Day, features the line “I’ll have what she’s having”?
If your room can’t get this one, you’re at the wrong event. But it’s a perfect warm-up for the movie section because everyone feels smart.
24. In the 2010 ensemble film “Valentine’s Day,” which two real-life couple played a couple on screen?
There were so many famous faces in that movie that people start naming pairs at random. The actual answer is more specific than most expect.
25. What 1990 film features a scene where a character uses a pottery wheel in what became one of the most iconic romantic scenes in cinema history?
The scene is more famous than the movie at this point. People under 25 have seen the parody before the original.
26. The 2004 film “The Notebook” is based on a novel by which author, who has become essentially synonymous with romantic fiction?
You’d think everyone knows this. You’d be wrong about 40% of the time.
27. In “Sleepless in Seattle,” the characters played by Tom Hanks and Meg Ryan don’t actually meet until what point in the movie?
This is the question that makes people realize how unusual that film’s structure really is.
28. What 2001 film features a scene where a man stands outside a woman’s door with cue cards declaring his love, while her husband sits inside?
This scene gets debated every single December and February. Is it romantic or is it deeply creepy? I’ve watched tables nearly flip over this question’s implications.
29. What animated Disney film features the spaghetti-sharing scene that became one of the most recognizable romantic images in movie history?
Easy, and that’s the point. After the Love Actually debate, the room needs a palate cleanser.
30. Which Shakespeare play, often performed around Valentines Day, features the line “The course of true love never did run smooth”?
People split between two plays on this one, and the wrong answer is almost always the same.
31. The 2018 horror film released on Valentines Day weekend that subverted the romantic holiday with home invasion terror was called what?
Horror fans perk up here. Everyone else looks nervous.
32. What 1981 slasher film set in a mining town was so heavily censored by the MPAA that the uncut version wasn’t seen for over 25 years?
Let me clean up that last one with a proper horror question. This film has a cult following for good reason.
33. Whitney Houston’s “I Will Always Love You” was originally written and recorded by which country music legend?
A classic trivia question, and it still catches people. The original version is so different in tone that people who’ve heard both sometimes don’t believe it’s the same song.
34. What 1977 Barry White song begins with a spoken-word intro and became one of the defining “mood music” tracks for Valentines Day?
Barry White’s voice is basically a valentines day trivia category unto itself. But one song stands above the rest.
35. The song “My Funny Valentine” comes from which Rodgers and Hart musical?
People know the song. Almost no one knows the show. And the show’s title is genuinely surprising.
36. What Celine Dion power ballad, featured in a 1997 blockbuster film, became one of the best-selling singles of all time?
This is a layup. But sometimes you need a layup, especially when you’re about to follow it with something harder.
37. Ed Sheeran’s “Thinking Out Loud,” one of the most popular first-dance wedding songs of the 2010s, was the subject of a copyright lawsuit alleging it copied what Marvin Gaye classic?
The lawsuit answer surprises people because once you hear both songs back to back, you can’t unhear it.
38. What 1975 song by Captain & Tennille became their only number-one hit and is still a Valentines Day staple?
The song is so associated with the era that people sometimes can’t separate it from the decade itself.
39. In Japan, Valentines Day has a unique tradition where only one gender gives chocolate. Which gender, and what’s the reciprocal holiday called?
This is one of my favorite valentines day trivia questions because it reveals how culturally specific our assumptions about the holiday are.
40. What do people in Finland celebrate on February 14th instead of romantic love?
Finland does its own thing. Always has. The answer is wholesome in a way that makes the rest of us look a little shallow.
41. In which country do people celebrate the “Festival of Love” (or Día del Amor y la Amistad) in September rather than February?
Latin America has some beautiful Valentine’s traditions, and this one catches people because the date is so far off from what they expect.
42. In Wales, what is the name of the patron saint of lovers, celebrated on January 25th with the exchange of carved wooden spoons?
The wooden spoon detail is what makes this question land. People picture it and something about the image is both funny and genuinely sweet.
43. In South Korea, there’s a third love-related holiday on April 14th for single people. What is it called, and what do participants eat?
This one always gets a laugh, and single people in the room suddenly feel very seen.
44. What do men in Denmark and Norway traditionally send women on Valentines Day, written in verse but signed only with dots representing each letter of the sender’s name?
The clue system is so clever. If the woman guesses who sent it, she gets an Easter egg later that year. If she can’t, she owes him one.
45. In the Philippines, mass wedding ceremonies on Valentines Day are sponsored by the government. What is the approximate number of couples who participate each year?
The scale of this catches everyone off guard. It’s not dozens. It’s not hundreds.
46. Valentines Day is banned or restricted in which of these countries: Saudi Arabia, Iran, Pakistan, or all three?
The answer is more complicated than people expect, and it’s shifted over time.
47. In Ghana, February 14th has been rebranded as what kind of day, celebrating a locally produced product?
I love this one because the answer is so specific and so perfectly Ghanaian.
48. In which European country is it tradition for women to receive gifts of small books on Valentines Day, connected to a festival also celebrating their patron saint?
The overlap between literature and love here is beautiful, and the answer isn’t one most people guess.
49. The human heart beats approximately how many times per day?
A perfect valentines day trivia question because it connects the symbol to the organ. People wildly overestimate or underestimate this number.
50. What chemical compound, released by the brain during the early stages of romantic love, is also found in chocolate?
This is why chocolate and Valentines Day are connected on a level deeper than marketing. The chemistry is real.
51. The “broken heart syndrome,” a real medical condition that can mimic a heart attack and is triggered by emotional stress, has what official medical name?
Every time I use this in a set, at least one person in the room has either experienced this or knows someone who has. It changes the energy completely.
52. When two people in love gaze into each other’s eyes, research has shown their heart rates do what?
The answer to this one is genuinely romantic in a way that science rarely is.
53. The iconic heart shape we draw on valentines doesn’t look much like an actual human heart. One theory suggests the shape was inspired by what plant, used as a contraceptive in the ancient world?
This is the kind of answer that makes people set their drink down. The connection between a love symbol and an ancient contraceptive is too perfect.
54. How long does the “honeymoon phase” of a romantic relationship typically last, according to most psychological research?
Couples in the room brace themselves for this answer. Some look relieved. Some look caught.
55. What was the original name of Necco’s conversation hearts when they were first produced in 1866?
The original product looked nothing like what we eat today, and the name reflects that.
56. Approximately how many conversation hearts are produced each year for Valentines Day?
The number is industrial. It reframes a tiny candy as a logistical operation.
57. In what year were emojis first added to conversation heart messages?
People guess much earlier than the actual date, probably because emojis feel like they’ve been around forever.
58. What flavor is the yellow conversation heart?
People eat these things every year and most have absolutely no idea what flavor they’re supposed to be. The confidence with which people guess wrong is beautiful.
59. Which famous author wrote love letters so explicit to his wife Nora that scholars were embarrassed to publish them for decades?
The contrast between this author’s public reputation and his private correspondence is staggering. I won’t quote them here, but they’re easily findable and absolutely unhinged.
60. Napoleon Bonaparte wrote passionate letters to which wife, who reportedly found them tiresome?
The one-sidedness of this correspondence is historically hilarious. Napoleon, conqueror of Europe, couldn’t get a text back.
61. Elizabeth Barrett and Robert Browning exchanged approximately how many letters during their courtship before eloping?
The volume of their correspondence tells you something about both the era and the intensity of their connection.
62. “How Do I Love Thee? Let Me Count the Ways” is Sonnet 43 from what collection?
The poem is universally known. The collection it belongs to is known by almost nobody outside English departments.
63. What famous playwright, known for a very different kind of writing, once said “A kiss is a lovely trick designed by nature to stop speech when words become superfluous”?
The quote is romantic. The person who said it is not who you’d guess.
64. What is the estimated total amount Americans spend on Valentines Day each year?
I mentioned this earlier in a per-person context, but the aggregate number hits differently. It’s a number that makes you think about what love costs, literally.
65. After greeting cards, candy, and flowers, what category of Valentines Day spending has grown the fastest in recent years?
The answer reflects how much the holiday has shifted in the last decade.
66. What percentage of people buying Valentines Day gifts are buying them for their pets?
This number is not small. And it keeps growing. I’ve watched people hear the answer and immediately decide they need to go buy their dog something.
67. Hallmark, the greeting card company, is often accused of “inventing” Valentines Day for profit. In what year did Hallmark actually start producing valentines?
People assume Hallmark started the whole thing. The timeline says otherwise.
68. Who is often called the “Mother of the American Valentine” for mass-producing elaborate lace valentines in the 1840s?
A woman who built a business empire out of paper and sentiment, and most people have never heard her name.
69. What day of the year sees the most marriage proposals in the United States?
Valentines Day feels like the obvious answer. And for once, the obvious answer is pretty close to right.
70. In the Victorian era, sending a nasty or insulting valentine was actually common. What were these called?
The Victorians had range. Their valentine tradition included both sincere love declarations and targeted cruelty, sometimes sent to the same person.
71. What city in the United States receives thousands of valentines each year to be re-mailed with its romantic postmark?
The town leans into it completely. Their postmark is the reason.
72. What animal, often associated with Valentines Day, is one of the few species that mates for life?
The animal kingdom’s approach to monogamy is more complicated than greeting cards suggest, but one species has become the poster child for lifelong partnership.
73. Alexander Graham Bell filed his telephone patent on what romantically significant date?
Sometimes history just hands you a coincidence that’s too perfect to ignore.
74. In 1929, what infamous event occurred on February 14th in Chicago?
This is the darkest valentines day trivia question in any set, and it’s also one of the most well-known. But the details still make people wince.
75. What is the name of the phobia describing the fear of falling in love?
There’s a word for this, and hearing it always makes people in the room go quiet for a second.
76. In 2023, what technology-driven trend became the most talked-about Valentines Day phenomenon?
If you’re reading this in a few years, this question will feel like a time capsule. Right now, it feels like the present.
77. What Valentines Day tradition, now largely extinct, involved young women pinning bay leaves to their pillows on February 13th?
The superstition is so specific that it feels made up. It isn’t.
78. The “X” used to represent a kiss at the end of a letter dates back to what practice?
People use “XOXO” without ever thinking about where it came from. The origin is older and more serious than they expect.
79. What fruit, now commonly dipped in chocolate for Valentines Day, was considered an aphrodisiac by the Aztecs?
Two different foods fit this description, and people split between them. Both are defensible, but one is more specific to Valentine’s Day.
80. The word “chocolate” comes from what Aztec word, and what did it originally mean?
The etymology connects two things people love: chocolate and linguistic trivia.
81. What is the most popular Valentines Day dinner reservation time in the United States?
Restaurant workers know this one instantly. Everyone else is guessing between two options.
82. What Italian dessert, whose name translates to “pick me up,” is a popular Valentines Day restaurant special?
A breather question. But the translation is the real gift here.
83. Oysters have been considered an aphrodisiac since ancient Rome. What amino acid found in oysters has been scientifically linked to increased hormone production?
This is one of those rare cases where the folk wisdom has at least some scientific backing.
84. What sparkling wine region in France is most associated with Valentines Day celebrations, and what makes wine from this region legally distinct?
Most people know the first part. The legal distinction is where it gets interesting.
85. What sitcom featured a famous Valentines Day episode where a character gets a turkey stuck on their head?
If you know, you know. And you can probably picture the exact moment.
86. In “The Office,” what does Michael Scott do to celebrate Valentines Day in the Season 2 episode “Valentine’s Day”?
Michael Scott’s approach to romance is a trivia category of its own. His Valentine’s Day episode is peak cringe.
87. What animated show created the concept of “Galentine’s Day” on February 13th?
This isn’t animated, and that’s the trap. People hear “created a holiday” and their brain goes to The Simpsons or Futurama. It’s a live-action show.
88. What reality TV show, which premiered in 2002, has become a Valentines Day viewing staple and has produced more than 25 seasons?
The longevity of this show is its own kind of love story. Between the franchise and its audience, at least.
89. In what “Peanuts” special does Charlie Brown famously not receive a single valentine?
This one hits a nerve. Everyone remembers the feeling, whether it happened to them or not.
90. What is the most popular day of the year for online dating app sign-ups?
It’s not Valentine’s Day. The actual answer tells you something about human psychology that’s both sad and hopeful.
91. What is the record for the longest kiss, set on Valentines Day?
People guess hours. The real answer is measured in days.
92. Approximately what percentage of Valentines Day cards are classified as “humorous” rather than sentimental?
This number has been climbing for years, and it says something about how the holiday’s tone has shifted.
93. What city holds the record for the largest box of chocolates ever made?
The box itself weighed more than some cars. The image of it is absurd and wonderful.
94. Teachers receive the most valentines of any profession. What profession comes in second?
Teachers are the obvious first guess, and they’re right. But the second-place finisher always gets a reaction.
95. What color was originally associated with Valentines Day before red became dominant?
Red feels so inevitable that imagining the holiday in any other color requires effort. But it wasn’t always this way.
96. Richard Cadbury, who created the first heart-shaped chocolate box, designed the boxes to be reusable. What were they intended to store after the chocolate was eaten?
The business model was the box, not the chocolate. That’s a level of marketing genius that still works today.
97. What Valentines Day tradition, started in Verona, Italy, involves writing letters to a fictional character?
The city takes this tradition seriously. There are real people whose job it is to respond.
98. The phrase “wearing your heart on your sleeve” may have originated from what medieval Valentines Day tradition?
Phrases we use without thinking almost always have origins stranger than we imagine. This one doesn’t disappoint.
99. What did a group of young women in Victorian England believe they would see if they looked through a twisted handkerchief at a candle flame on Valentine’s Eve?
The specificity of Victorian love superstitions never gets old. The rituals were elaborate, dead serious, and completely bonkers.
100. In 2004, the Mars rover Opportunity landed on Mars and sent back images of its landing site. NASA named the landing area “Eagle Crater,” but the mission itself had launched on what date, giving it a connection to Valentines Day that most people have never heard?
This isn’t quite right, so let me give you the real version. The question I’ve saved for last is this:
On February 14, 1990, the Voyager 1 spacecraft turned its camera back toward Earth from 3.7 billion miles away and took a photograph. What did Carl Sagan famously call that image?
I close with this one every time I run a Valentine’s set. Because after a hundred questions about candy hearts and rom-coms and chocolate boxes, this is the one that puts it all in perspective. On Valentine’s Day, from farther away than any human-made object had ever been, a spacecraft looked back at everything we’ve ever loved. Every valentine ever sent. Every heartbreak. Every first kiss. All of it, in a single pixel of light.
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