144 "This Or That" Questions That Really Make You Think

Sometimes, the conversationalist in you takes a sabbatical — usually at the most inopportune times. Maybe your snappy quips are having a short-circuit moment or you're dealing with a bout of social anxiety as you’re getting to know someone new. It’s moments like these when some simple, tried and true “this or that” questions come in handy.

The game is pretty straightforward: Present your counterpart with two options and they must choose one over the other. No skipping, no choosing both. One answer must come out on top. The “this or that” questions game is not only a quick go-to for lulls in conversation, but you’d be surprised just how deeply these little prompts can allow you to get to know a person. There’s always more to learn about someone, even your besties or significant other. You never know which question may launch them into a full-fledged storytime. It’s also a surefire way to suss out which friendships or dates have the most in common with you and also makes a highly entertaining party game — cocktails optional.

Icebreakers don’t have to be boring or cliche. The best “this or that” questions will make you think, laugh, debate, and get to know your friends, coworkers, or significant other on a whole new level. Whether you’re just playing for giggles over drinks or looking to spark a deep discussion, these are the conversation starters you’ll want in your chit-chat arsenal to bring you closer to the people around you.