44 Clever Conversation Starters That’ll Put an End to Awkward Silences

published Nov 29, 2023
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A group of friends during a dinner party having fun together, talking and drinking wine
Credit: Hinterhaus Productions / Getty Images

Make holiday entertaining less frantic and more fun with our guide to the best hosting hacks and tips. This content is presented in partnership with Shipt; it was created independently by our editorial team.

In an extremely online world, IRL gatherings seem more daunting. Sure, come with food, drinks, and hopefully a friend or two to spend time with. But what about chatting up people you aren’t familiar with or haven’t seen in a while? You don’t want to leave an event thinking about all the awkward silences. 

“There [are] a lot of people coming to me right now, and they’re saying, ‘I don’t know how to have a conversation anymore unless I’ve got notes in front of me on Zoom,’” says Cathleen Hanson, director of the International School of Protocol

This is where preparation can help. Enter: clutch conversation starters.

Anna Page, an influencer who’s been to her fair share of parties and professional events, swears by keeping it simple. Even a seemingly innocuous question can open the room to a lively, organic discussion. The creator of The Page Edit recalls a fun starter that sparked plenty of interest at a holiday party: “A topic of conversation that came up was, ‘What is [your] biggest ick?’” She says that the “hilarious conversation” lasted about an hour.

If you’re not talking to perfect strangers, draw on anything you can recall. “It makes things easier when you’re able to reconnect with someone by paying attention to what you spoke about before,” Hanson says. 

As hosts, Page and her husband, Nathan, break the ice with unconnected friends to make every guest feel welcome. “It goes pretty well when we highlight things like, ‘Hey, she’s from Washington, DC; didn’t you go to college there?’” 

Credit: FilippoBacci / Getty Images

Whether you’re tasked with hosting or joining the festivities as a guest, having in your back pocket can give you the confidence to mingle more. Here are 44 options to get the ball rolling.

Pop Culture

  1. What’s the most “embarrassing” song on your Spotify Wrapped this year?
  2. Would you stay at a White Lotus hotel?
  3. Who’s your favorite celebrity couple?
  4. What’s your go-to karaoke song?
  5. What podcast are you loving right now?  
  6. What popular movie/TV franchise have you never watched or don’t get the hype about?
  7. What’s your Roman Empire?
  8. What’s your most-used emoji?
  9. What book do you wish you could read again for the first time? 
  10. Have you ever met a celebrity?

Food and Drink

  1. You can only keep one: PSL, peppermint mocha, or gingerbread latte. Which is it? 
  2. What’s your gas station road trip snack?
  3. Is a hotdog a sandwich?
  4. What fast-food drive-thru do you always want to stop for?
  5. Dishes: Do you clean them right after cooking, or do you let them chill?
  6. Breakfast for dinner: yay or nay? 
  7. When you cut a sandwich in half, do you make triangles or rectangles?
  8. What’s the most complicated meal you’ve ever made?
  9. What’s your go-to Chipotle order? 
  10. New York- or Chicago-style pizza? 

Life

  1. What was your favorite age and why?
  2. What’s the silliest childhood nickname someone gave you?
  3. What cheesy inspirational quote do you secretly love?
  4. Three-day weekends — do you want Monday off or Friday off? 
  5. What’s a random fact that surprises you?
  6. What’s your biggest ick?
  7. What’s your favorite holiday activity you have to do every year?
  8. What are you most thankful for from the past year?
  9. What’s the best gift you’ve ever gotten?
  10. What’s a great piece of advice that sticks with you?
  11. What is a home, craft, or other project you’ve done recently that you’re proud of?  
  12. What’s the funniest thing your pet has ever done?
  13. Are you an early bird or a night owl?

Travel

  1. Best form of travel: train, plane, or automobile?
  2. What’s the most memorable souvenir you’ve ever gotten on a vacation? 
  3. Do you have any exciting upcoming trips?
  4. Do you prefer to stay at a hotel or rent a house? 
  5. What’s the most annoying thing you’ve had to buy in an airport because you forgot to pack it?
  6. You’re going to the beach: Do you prefer a lake or an ocean?
  7. Fanny pack: yay or nay? 
  8. You have to choose one: Disney World or Disneyland. Which is it?
  9. When do you get to the airport: Three hours early or as the boarding door is closing? 
  10. What’s your favorite place you’ve ever visited?
  11. Do you have a vacation horror story that makes you laugh now?