How to Actually Start a Conversation Online (Without Saying 'Hey')

We've all been there: staring at a chat box, fingers hovering over the keyboard, defaulting to the most common (and least exciting) opener—"hey." While there's nothing wrong with a simple greeting, it's rarely the spark that ignites a real, engaging conversation. If you want to stand out and actually connect with someone online, it's time to get creative.

Here are some ways to kick off a chat that actually goes somewhere:

1. Ask a Fun, Unexpected Question

Instead of "hey," try something that invites curiosity or personal input:

• "If you could instantly master any skill, what would it be?"
• "What's the most random fact you know?"
• "Pineapple on pizza—yes or no?"

Questions like these give the other person something to react to and show you're genuinely interested in their thoughts.

2. Make a Playful Observation

Look for anything in their profile picture (if applicable) or your shared context that you can comment on:

• "You look like someone who has strong opinions about breakfast food. True?"
• "This chat feels like a blind date and a game show all at once."

A clever or lighthearted comment breaks the ice and helps move past small talk.

3. Share Something About Yourself

Vulnerability opens doors. Lead with a quirky confession or a relatable tidbit:

• "I just spent 20 minutes trying to name my houseplants. Want to help?"
• "I’m here to avoid doing laundry. What about you?"

This invites reciprocity and gives your chat partner something to latch onto.

4. Use Humor to Your Advantage

If you can make someone smile from the start, you're already winning:

• "Okay, I’m legally required to tell you I’m terrible at small talk. Proceed with caution."
• "This is a conversation starter disguised as a human being."

5. Comment on the Experience

If you're on a random chat platform like Chitchat.gg, your shared experience is the context:

• "Ever have a chat on here that totally surprised you?"
• "So, are we making internet history right now or just passing time?"

Final Thoughts

Starting a conversation online doesn't have to feel awkward or generic. By showing a bit of personality, curiosity, or humor right off the bat, you're much more likely to spark something real.

So next time you’re tempted to type “hey,” pause—and try something a little more you.

You never know where one great opening line can take you.