Online Icebreakers That Aren’t Lame

Let’s be real: most icebreakers suck. “What’s your favorite color?” is fine when you’re six. But when you’re meeting someone online, whether it’s through a random chat, a dating app, or a virtual meetup, you want something that actually sparks a real conversation.

So if you’re tired of asking or answering “hey, what’s up?”, here’s a list of online icebreakers that are actually interesting, unexpected, and way less awkward.

1. “If you had to delete every app on your phone except three, which would you keep?”

This gives insight into someone’s personality, priorities, and habits in a fun, low-pressure way.

2. “What’s something totally random you’re weirdly good at?”

It invites a personal and often funny answer, and usually leads to more great stories.

3. “If your life right now had a background soundtrack, what song would be playing?”

Music-based questions tend to hit deeper than you’d expect, and this one adds a layer of personality and emotion.

4. “What’s the most harmless hill you’ll die on?”

People have strong (and hilarious) opinions about things like cereal milk or how to hang toilet paper. Lean into it.

5. “Tell me something that made you laugh recently.”

It brings immediate good vibes and gets the other person thinking positively right away.

6. “Would you rather have a rewind button or a pause button for life?”

Classic would-you-rather with a thoughtful twist. Great for opening up deeper chats.

7. “What’s the most interesting place you've ever talked to someone online from?”

Perfect for global platforms and random chats, people love sharing their digital travel stories.

8. “If aliens landed and asked you to explain the internet in one sentence, what would you say?”

Unexpected, imaginative, and guaranteed to spark creativity.

9. “What’s a conspiracy theory you 100% don’t believe, but secretly wish were true?”

Funny and weird in the best way. Keep it playful, not polarizing.

10. “Okay, serious question: what’s your go-to comfort food?”

Food brings people together. Always has, always will.

Final Thought

A good icebreaker does two things: it lowers the pressure and opens the door to real connection. So the next time you’re meeting someone online, ditch the boring openers and try one of these instead.

Because the best conversations don’t start with “hey”, they start with curiosit