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100 Fun 'This or That' Questions to Spark Deeper Connections

If you're searching for fun icebreaker questions, a simple way to start conversations, or a fresh activity for team-building, “This or That” questions are the perfect go-to tool. These quick either/or choices are an excellent way to reveal personality traits, uncover hidden preferences, and spark deeper conversations. According to the American Psychological Association, structured question games can meaningfully improve social bonding and interpersonal understanding—yes, these questions really work.
Whether you’re hosting a party, planning a road trip, preparing a classroom activity, or warming up a meeting, this list of 100 This or That questions spans food, entertainment, travel, lifestyle, work, holidays, and more. Feel free to copy, play, and share.
To support your creative expression beyond text alone, you can also transform any of these prompts into multi-format stories (text + photos + videos) on Tellsomething, a platform designed for emotional expression and visual storytelling.

1–15: Food & Drink

  1. Hot Dogs or Hamburgers?
  1. Apple or Android?
  1. Tacos or burritos?
  1. Ice Cream or Milkshakes?
  1. Coffee or tea?
  1. French Fries or Onion Rings?
  1. Bagels or Donuts?
  1. Smoothies or Milkshakes?
  1. Cupcakes or cookies?
  1. Waffles or pancakes?
  1. Peanut Butter or Nutella?
  1. Hot chocolate or iced coffee?
  1. Ketchup or mustard?
  1. Pizza or pasta?
  1. Sushi or tacos?

16–25: Entertainment

  1. TV Shows or Movies?
  1. Video Games or Board Games?
  1. Reading Books or Audiobooks?
  1. Fiction or Non-Fiction?
  1. Podcasts or Music?
  1. Live Concerts or Sports Events?
  1. Comedy Shows or Drama Series?
  1. Horror Movies or Romantic Comedies?
  1. E-books or Physical Books?
  1. Superhero Films or Sci-Fi Films?

26–35: Travel & Adventure

  1. Beach Vacation or Mountain Retreat?
  1. Road Trip or Air Travel?
  1. Camping or Glamping?
  1. City Exploration or Nature Hike?
  1. Time Travel to the Past or the Future?
  1. Teleportation or Flying?
  1. Snowboarding or surfing?
  1. Staycation or Vacation Abroad?
  1. Theme Park or Water Park?
  1. Guided Tour or Exploring Solo?

36–45: Technology & Media

  1. Social Media or Real-Life Interaction?
  1. Texting or calling?
  1. Streaming Music or Vinyl Records?
  1. Online Shopping or In-Store Shopping?
  1. Emails or Handwritten Letters?
  1. Netflix or YouTube?
  1. Digital Calendar or Paper Planner?
  1. E-Reader or Tablet?
  1. Desktop Computer or Laptop?
  1. Smartwatch or Traditional Watch?

46–55: Lifestyle & Personal Preferences

  1. Early Bird or Night Owl?
  1. Introvert or Extrovert?
  1. Formal Wear or Casual Attire?
  1. Minimalist or Collector?
  1. Yoga or Cardio Workout?
  1. Dog Person or Cat Person?
  1. Reading Minds or Teleportation?
  1. High-Tech Gadgets or Vintage Items?
  1. Live in the City or Countryside?
  1. Dine in or takeout?

56–65: Fun & Games

  1. Board Games or Card Games?
  1. Trivia or Charades?
  1. Puzzles or Video Games?
  1. Sports or arts and crafts?
  1. Truth or Dare?
  1. Team Sports or Individual Sports?
  1. Strategy Games or Action Games?
  1. Laser Tag or Paintball?
  1. Karaoke Night or Dance Party?
  1. Roller Skating or Ice Skating?

66–75: Fashion & Style

  1. Jeans or sweats?
  1. Sneakers or Boots?
  1. Dresses or Pants?
  1. Hats or Scarves?
  1. Bright Colors or Neutral Tones?
  1. Gold Jewelry or Silver Jewelry?
  1. High Heels or Flats?
  1. Sweaters or Hoodies?
  1. Piercings or Tattoos?
  1. Designer Brands or Thrift Finds?

76–85: Work & Education

  1. Work from Home or Office?
  1. Solo Projects or Team Projects?
  1. Long Commute or Relocate Closer?
  1. Email Communication or Face-to-Face Meetings?
  1. Career or Family?
  1. Learn a New Language or a Musical Instrument?
  1. Hands-On Learning or Theoretical Study?
  1. Internship or Part-Time Job?
  1. Public Speaking or Writing Reports?
  1. Dream Job or High-Paying Job?

86–95: Holidays & Seasons

  1. Summer or winter?
  1. Halloween or Christmas?
  1. Spring Flowers or Autumn Leaves?
  1. Rainy Days or Sunny Days?
  1. Beach Day or Snow Day?
  1. Fireworks or Parades?
  1. Pumpkin Spice or Peppermint Mocha?
  1. Camping in a Tent or Staying in a Cabin?
  1. Picnic in the Park or Backyard BBQ?
  1. New Year's Eve Party or Quiet Night In?

96–100: Random Fun Questions

  1. Dogs or Cats?
  1. Super Strength or Invisibility?
  1. Books or Movies?
  1. City Life or Country Life?
  1. Dream House or Dream Job?

Conclusion

“This or That” questions are a simple yet powerful way to spark conversations and build stronger connections—whether you're meeting someone new, bringing energy to a group setting, or breaking the ice at work. They reveal personalities, start deeper discussions, and often lead to unexpected discoveries.
If you want to turn these prompts into creative content or capture your moments with richer expression, try sharing them through Tellsomething, a platform that supports multi-format storytelling—text, photos, and videos—so your conversations and memories become more vivid and meaningful.
Ready to explore, share, and express more?
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