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20 Fun Valentine's Day Questions & Trivia


20 Fun Valentine's Day Questions & Trivia

Whether you’re staying home or going out for a fun dinner, here are 20 fun questions and trivia to share with your Valentine on Valentine’s Day this year! Have fun with these!

After you finish all 20, get over 500 more awesome questions from our new game 501 Questions: A Travel Game!

20 Fun Valentine's Day Questions & Trivia

Would You Rather:

  1. Have a fun new experience together or get a gift you’ve been wanting for awhile for Valentine’s Day?

  2. Get a box of chocolates or flowers on Valentine’s Day?

  3. Stay in or go out for Valentine’s Day?

  4. Me read a love letter I’ve written to you or have me do something for you that means I love you. If your answer is to do something, what would that something be?

  5. Plan your Valentine’s date together or get surprised with a whole date already planned?

This last question is from my creative friend Margo:)

If You Could:

  1. Relive one experience we’ve shared together, what would it be?

  2. Improve our relationship in one way, what would it be?

  3. Name three traits you love about me, what would they be?

  4. Say one new experience you want to share this year together, what would it be?

  5. Win the lottery today, what would you do with your winnings for Valentine’s Day?

20 Fun Valentines Day Questions Trivia Conversation Starters

Tell Me About:

  1. The moment you knew you loved/liked me.

  2. Your first impression of me.

  3. Your craziest Valentine’s Day memory.

  4. My best physical feature.

  5. Your favorite memory of us dating.

Valentine’s Day Trivia:

I found all of these fun trivia questions from Valentines Day Trivia Quiz. It was so fun to play, I wanted to share my favorites with you and see if you can guess the answers.
  1. “How many cards are sent on Valentine’s Day each year? Is it 500 million, 1 billion, 2 billion, or 10 billion cards?”

    Answer: “The Greeting Card Association estimates that approximately one billion valentine cards are sent world-wide each year, making Valentine’s Day the second largest card sending holiday of the year behind Christmas.”

  2. “What percentage of flowers purchased on Valentine’s Day are red? Is the answer 69%, 76%, 83%, or 94%?”

    Answer: “According to the Ipsos-Insight for the American Floral Endowment’s Consumer Tracking Study (2004), of roses purchased on Valentine’s Day, 69% are red, 6% pink, 6% peach/salmon, 5% yellow, 4% white, 7% mixed, 4% other.”

  3. “Who created the first Valentine’s Day box? Is it Russell Stover, Louis IV, Richard Cadbury, or Milton Hershey?”

    Answer: “In 1822, John Cadbury opened a tea and coffee shop in Birmingham, England. He soon expanded chocolate manufacturing and in 1861 his son Richard greatly increased sales by packaging Cadbury chocolates in the world’s first heart shaped box for Valentines Day.”

  4. “What do the X’s and O’s in XOXO stand for?”

    Answer: “X=kisses, O=hugs”

  5. “What continent produces the most roses sold in the U.S. on Valentine’s Day?”

    Answer: “South America. Most roses sold on Valentines Day in the U.S. are imported from South America, but California grows 60% of the roses sold in the U.S.”

  6. “How many U.S. states have a city named Valentine? Is it 3, 4, 5, or 7?”

    Answer: “Four. Valentine, Arizona; Valentine, Nebraska; Valentine, Texas; Valentine, Virginia.” Which one will you visit first?:)

Save these for Later!

1. Pin this post to use later here.

2. And, download these conversation starters so you can easily pull them up later!

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Fun Christmas Questions & Trivia for You, Your Family, and Friends


Fun Christmas Questions & Trivia for You, Your Family, and Friends

20 Fun and Free Christmas Conversation Starters

Whether you’re relaxing around the Christmas tree together or in the car on a long road trip over the holidays, here are 20 fun questions and trivia to spark fun new conversation for you, your family and friends. Have fun!

20 Fun Christmas Questions & Trivia

Would You Rather:

1. Have a white Christmas or a warm Christmas?

2. Receive a gift or share an experience?

3. Receive eggnog or fruit cake as a gift?

4. Play outside, build a snowman, and sled or stay inside drinking hot chocolate and reading a good book when it snows?

5. Shop in New York City for gifts or shop online in your pajamas?


If You Could:

1.     Have Christmas at home or in a new destination, what would you choose?

2.     Only have one Christmas song available to hear over the Christmas season, which one would you choose?

3.     Start a new tradition, what would it be?

4.     Spend Christmas at the beach or in the mountains, what would you choose?

5.     Plan your Christmas Eve and Christmas Day meals, what would you plan to have?

Fun Christmas Questions and Trivia for Family and Road Trips


Tell Me About:

1. Your favorite Christmas tradition.

2. Your favorite memory playing in the snow.

3. Your craziest or most memorable Christmas experience.

4. The best gift you’ve ever received.

5. Your favorite Christmas ornament.


Christmas Trivia:

1. What country is known to have started the Christmas tree tradition?

Answer: Germany.

2.  What Christmas song was the first to be broadcast from space in 1965?

Answer: Jingle Bells. Cool!

3. What Christmas decoration was originally made from tin?

Answer: Tinsel. When we lived in Vermont for a summer, we met David Claggett from Artistry in Tin who still makes traditional tin tinsel!

4.  What traditional Christmas decoration is actually a parasitic plant?


5. What state is home to a town named Christmas?

Florida. I found other Christmas towns from this article. There’s also: Bethlehem, Pennsylvania; Santa Claus, Indiana and Santa Claus, Georgia ; North Pole, Alaska; Snowflake, Arizona; Noel, Missouri; Rudolph, Wisconsin; Evergreen, Alabama; Joy, Illinois; Christmas Valley, Oregon

Save these for Later!

1. Pin this post to use later here.

2. And, download these conversation starters so you can easily pull them up later!

Name *
20 Fun Christmas Questions & Trivia

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Get 501 fun new conversation starters with our new game 501 Questions: A Travel Game!

"Such great conversation starters!" -Tracy K.,


"The questions have us laughing, deeply pondering, and digging deep into interesting conversations." -Lindsay M.,


20 Conversation Starters for Thanksgiving


20 Conversation Starters for Thanksgiving

Need conversation starters for Thanksgiving? We got you!

20 Conversation Starters for Thanksgiving,

Thanksgiving can bring on a whole range of emotions: excitement to get everyone together, dread of pending political conversations, anxiety as to what to talk about with family you only see every five years, or boredom hearing the same old stories over and over from Grandpa.

Here’s 20 questions to spark fun and new conversations with your family and friends during your Thanksgiving get togethers.

We’ve used these with our families and it’s amazing the new stories you hear, the new things you learn about your family, and new perspectives that come through new conversation. Enjoy!


20 Questions for Thanksgiving

Would You Rather:

1. Meet one of your ancestors from the past or a descendant in the future?

2. Take your next trip by plane, train, car, or boat?

3. Travel with a map or explore without a map?

4. Be a generalist or an expert?

5. Know your future or not know your future?

If You Could:

6. Write a book about your life, what would the theme of your book be?

7. Choose between exploring the depths of the oceans or flying into space, which one would you choose?

8. Travel to three countries next year, which countries would you choose?

9. Relive a season of your life, what season would it be?

10. Try something new you’ve been curious about, what would you want to try?

Tell Me About:

11. A time you were courageous.

12. Something you’re looking forward to this year.

13. One of your favorite memories from your childhood.

14. A time a stranger changed your life.

15. The best piece of advice someone gave you and the worst piece of advice you’ve received. 

Travel Trivia:

16. What city is known as the Mother of the World?

Answer: Cairo, Egypt

17. Guess three of the seven countries that have territorial claims of the south pole?

Answer: Norway, Australia, France, UK, New Zealand, Chile, Argentina. Other countries present at the south pole have research facilities on other country’s territories.

18. Which country has the most languages spoken?

Answer: Papua New Guinea, with 820 languages spoken

19. What country is credited for building the first modern car?

Answer: Germany by Karl Benz in 1885

20. What are three of the world’s seven natural wonders?

Answer: Mount Everest in Nepal, Victoria Falls in Zambia/Zimbabwe, Grand Canyon in Arizona, USA, Great Barrier Reef in Australia, Northern Lights, Parícutin volcano in Mexico, Harbor of Rio de Janeiro, Brazil

Save These for Later!

1. Pin this post to use later here.

2. And, download these conversation starters so you can easily pull them up later!

Name *
20 Conversation Starters for Thanksgiving,

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