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30 Holiday Questions to Ask your Fiancé

The holiday season can sometimes be cliché with all the pictures of cute boots and pumpkin spice lattes. Even so, I want to encourage you to embrace fall and the holidays to come with your other half.

Take some time to step away from the potential holiday stress, and the wedding planning, to come and take pleasure in getting to know your fiancé a little bit more with these fun seasonal questions.

Make the most of a new season and find fresh ways to connect.

Take your fiancé out to enjoy their favorite seasonal holiday drink or treat and spark new conversation with these questions.


  • What was your most memorable holiday as a kid?

  • What are your favorite holiday treats?

  • What is your funniest holiday memory?

  • What is your favorite holiday scent?

  • Do you prefer hot chocolate or apple cider?

  • How do you feel about pumpkin spice?

  • Have you ever jumped into a pile of leaves?

  • What is your favorite thing about fall?

  • What sort of fall events did you enjoy as a kid (such as apple picking, pumpkin patches, corn mazes)?

  • What was your favorite Halloween costume as a kid?

  • When was your scariest Halloween?

  • What do you like most about Halloween?

  • What are your favorite Thanksgiving traditions?

  • What is your favorite Thanksgiving recipe?

  • What are you most thankful for this year?

  • What are your favorite Christmas traditions?

  • What is the best Christmas gift you have ever received?

  • What is one gift you asked for and never received?

  • What is the weirdest gift you have ever received?

  • How long did you believe in Santa?

  • Have you ever had a white Christmas?

  • What is your favorite Christmas movie?

  • What are your favorite winter activities?

  • What new recipe would you like to try this season?

  • What is a new tradition you want to make happen this year?

  • Who would you like to be intentional about thanking in this season of thanksgiving?

  • In what ways would you like to give to others this season?

  • What would be the best holiday date?

  • What goals would you like to concentrate on before the year is up?

  • What are you most excited for this season?

Want more questions? We’ve got you covered. In fact, we have an entire book with 365 Connecting Questions for Engaged Couples to get you talking, laughing and learning more about each other.