50+ Conversation Starters for Awkward Family Gatherings

50+ Conversation Starters for Awkward Family GatheringsThe holidays can be an awkward time. Having to sit around and chat with family members you normally don’t communicate with is intimidating.

Imagine yourself on the sofa flanked on either side by your 80 year old granny and an overly curious 5-year-old niece. What will you all talk about?

Please, don’t bring up the weather. You can do so much better than that. Really. You can make a lasting impression this year by helping your family to bond and create new memories. Whether you’re gathering with your own flesh and blood or your lovely in-laws, we’ve got a boatload of chat topics and games to keep the crickets from sounding off. These conversation starters will also keep everyone from relying on their phones and tablets to pass the time away!

The “Would You Rather” Game

How it works: Each family member takes turns asking, “Would you rather…” questions. It’s up to you and your clan to come up with crazy choices to make. A couple of fun examples:

  • “Would you rather travel into the past to meet your ancestors, or travel into the future to meet your grandchildren?”
  • “Would you rather be considered totally weird and awkward, or average with no unique or special qualities?”
  • “Would you rather know how to speak every language fluently, or know how to play any and every musical instrument?”

Plan ahead by getting great questions from the official Would You Rather website.

Reminisce with granny

In case you didn’t know, Baby Boomers tend to carry a lot of wisdom. But that knowledge rarely gets passed down because let’s face it: no one wants to sit around and listen to granny babble about the olden days. But don’t doubt the matriarch of the family – you’re all in for an entertaining treat! Get the whole clan together and make a concerted effort to gather some family history. Have granny or the oldest person present tell you all about how life was growing up back in the day. Don’t forget to get their insight on how things have changed, especially how they did certain tasks before technology took over. Think of it as story time without a book. You’ll walk away with a whole new perception of your loved one and great stories to pass down to future generations.

Have a joke fest

Find a friendly website or app chock full of kids jokes and let the little ones compete to see who can make the family LOL. Childhood Beckons is a popular destination for kid-friendly laughs.

If you prefer not to think too hard and need more specific suggestions, we’ve done all the work for you. Here’s 50 questions to get to know your relatives a little better.

  1. If you had to teach a class for a day, what subject would be natural for you?
  2. What other family member present do you think you most look or act like?
  3. What would you ask your pet if it had the ability to answer you back?
  4. Besides a loved one, what is one thing you could never live without?
  5. If you became President, what is the first thing you would do to make the country a better place?
  6. What is something you got away with as a child that your family still doesn’t know about?
  7. If you were stranded on an island for eternity, name one book or CD you would need to have in your possession.
  8. If you could start your dream job tomorrow, where would it be and what would you do?
  9. If you had to choose between being the smartest person in the world or the most beautiful, which would you pick and why?
  10. Who is the best cook in the family?
  11. If you could travel anywhere in the world, where would it be?
  12. If you had one wish (and you can’t wish for more wishes), what would you wish for and why?
  13. What is your biggest fear?
  14. If you could trade places with your parents for a day, what would you do differently?
  15. In your opinion, what is the worst movie of all time?
  16. If you could pick your own name, what would it be?
  17. If you could be an animal, what would you be and why?
  18. At a restaurant, do you tip based on the level of service, or based on the bill itself?
  19. If you could be a famous person for a week, who would you be and why?
  20. Describe the worst dream you’ve ever had.
  21. What celebrity or icon do you think would make a good politician?
  22. If you could play any instrument, what would it be and why?
  23. What is your favorite book and why?
  24. What has been the happiest day of your life so far and why?
  25. If you could only eat three foods for the rest of your life, what would they be?
  26. What is the craziest thing you’ve ever eaten?
  27. What is your earliest memory?
  28. What has been your most embarrassing moment?
  29. How long could you go without looking checking your social media accounts?
  30. If you could have dinner with anyone (past or present), who would it be and why?
  31. What is the most beautiful place you have ever seen?
  32. What do you think is your best physical feature?
  33. If you could move to any country tomorrow, which country would you go to?
  34. What is your greatest talent or ability?
  35. What two items would you grab if your house was on fire?
  36. If you could travel back in time, where would you go?
  37. What is something you’ve always wanted to to learn how to do, and what’s stopping you from learning it?
  38. Do you have any habits you think are unusual or quirky?
  39. If you were invisible for a day, what would you want to observe?
  40. If you had the attention of the world for just 10 seconds, what would you say?
  41. Would you rather have the power to be invisible or read minds?
  42. If our family had a theme song, what would it be?
  43. Our family is most like what TV or movie family?
  44. If you could change your age, what age would you rather be and why?
  45. What Hollywood actor or actress would do a good job playing you in a movie?
  46. If your best friend wrote a book about you, what would the title be?
  47. If your worst enemy wrote a book about you, what would the title be?
  48. Be honest: Which reality TV show is your guilty pleasure?
  49. Which cartoon character are you most like?
  50. How much money would it take for you to bungee jump over the Grand Canyon?

We want to hear from you! What are your ideas for keeping the conversation going at family gatherings?

Need more help dealing with those pesky relatives? Be sure to read How to Deal with Annoying Family Members.

Photo Credit: Shutterstock / Monkey Business Images

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