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21 Good Conversation Starters to Make Your Holiday Less Stressful

Emily Hale
Emily Hale

November 30, 2015

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I have the blessing of being close with my extended family. We see each other often throughout the year, so the holidays are just an excuse for one big party. If there’s any awkward going around, it’s because we’re being silly, not because we’re uncomfortable.

But there are those points in the conversation, even with my family, where I run out of things to say and I end up staring blankly, nodding, and saying, “So yeah….” It’s in those kinds of circumstances that I find Misha’s post, “Six Tips to Avoid Awkward Conversation,” helpful.

One of Misha’s handy tips is to ask good questions. Sometimes, though, it’s hard to think beyond the basic “How have you been lately?” While that’s not a bad topic, it is difficult to have a good conversation when the common response is often “Good! How about you?”

It’s a circular question that takes the conversation nowhere and causes you some serious mid-conversational stress as you flounder for a new topic. Plus, there are other far more creative ways to start a deeper conversation.

So I thought I would help you out by giving you some good questions that will jumpstart deep, interesting conversations this holiday season (and hopefully relieve a little pre-party anxiety).

21 Good Conversation Starters

  1. Are you enjoying your work?
  2. What does your typical work day look like?
  3. What kinds of jobs did you have when you were in college?
  4. When you were my age, how did you balance your class schedule, work, and social life?
  5. Is there anything you wish you had done differently in your college years?
  6. Is there something you did in your college years that you would recommend?
  7. Based on what you know now, would you have chosen a different major? Would you have started college right out of high school?
  8. Have you thought about any New Year’s Resolutions?
  9. Who is your favorite superhero?
  10. Have you seen any movies recently?
  11. What kind of music do you enjoy?
  12. How do you like to spend an hour of free time?
  13. What’s your Myers-Briggs personality type?
  14. Have you discovered any new restaurants you like?
  15. Have you read any good books lately?
  16. What has life been teaching you?
  17. What has [insert child’s name] been up to?
  18. What is one of your favorite holiday memories?
  19. What are you most grateful for today?
  20. What do you like doing when you’re not in school?
  21. What is your favorite thing to do with your family?

A few key things to keep in mind before launching into your holiday conversations….

Ask follow-up questions and say “Tell me more about that.” Sometimes people don’t know how long they should talk about a particular subject. Asking “Why?” and “How?” or asking them to expand on what they’ve already said gives your family or friends the permission they need to continue talking about something they enjoy or are passionate about.

Be prepared to talk about yourself. If you ask your cousin what he enjoys doing in his free time, have your own answer to the same question in mind. People often enjoy returning the question.

This isn’t about you. Asking questions is about making the other person feel heard. Don’t ask questions only to figure out a way to insert your opinion or experience into the conversation. Take the time to listen and learn.

Political discussions are inevitable, but they don’t have to be a catastrophe. You don’t have to try to avoid them, but you also shouldn’t purposefully make inflammatory comments or get offended. Instead, make it your priority to understand where the other person is coming from and ask questions that make them think about what they believe.

Finally, and most importantly, this is a conversation, NOT an interrogation. Don’t rush this. You are not solely responsible for keeping the conversation going by asking everyone questions. It’s not worth stressing out over. Just let things happen and follow the flow. Good luck and have fun!

For more holiday survival tips, check out Six Tips to Avoid Awkward Conversation.

Emily Hale
Emily Hale

Emily is an Unbound student majoring in Communications. People are her passion and there is nothing she enjoys more than engaging and encouraging. She writes at about faith and daily living.

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