How to Use “Who’s Most Likely To” as a Conversation Starter

“Who’s Most Likely To” might seem like just a party game—but in the right setting, it’s a powerful tool to get people talking, laughing, and opening up. Whether you’re hanging with new friends, breaking the ice on a first date, or trying to get coworkers to relax, this game has a sneaky superpower: it starts conversations that actually go somewhere.

In this post, we’ll show you how to turn those quick questions into deeper discussions, and why “Who’s Most Likely To” might just be the best icebreaker you didn’t know you needed.

Why It Works: The Psychology of Playful Curiosity

When you ask “Who’s most likely to move to another country on a whim?” or “Who’s most likely to own 12 cats?”, you’re doing more than just pointing fingers—you’re creating a shared window into personality, values, and quirks.

It’s low-pressure, fun, and just weird enough to bypass the awkwardness of small talk. Plus:

• It doesn’t put anyone on the spot (you can vote instead of talking)
• It invites humor and honesty
• It naturally leads to storytelling (“Oh my gosh, remember when…?”)

Perfect Times to Use WML as a Conversation Starter

💡 First Dates or Dating Apps
Break the cycle of “what do you do for work?” by asking something like:

• Who’s most likely to go viral on TikTok without realizing it?
• Who’s most likely to have a secret hobby no one expects?

💡 New Roommates or Travel Buddies
Whether you’re living together or hitting the road, break the ice fast:

• Who’s most likely to hog the bathroom?
• Who’s most likely to become best friends with a stranger on the plane?

💡 Coworker Hangouts or Team Intros
Great for onboarding, happy hours, or remote teams:

• Who’s most likely to send a meme in the middle of a serious meeting?
• Who’s most likely to win “Employee of the Month” without trying?

💡 Meeting Your Partner’s Friends or Family
Feel like the new kid in the group? WML is a fun way to join in without feeling awkward.
Stick to light-hearted questions like:

• Who’s most likely to forget someone’s birthday (but make up for it in a big way)?
• Who’s most likely to host an unforgettable dinner party?

How to Go From “Just a Game” to Real Conversation

Want the game to lead somewhere meaningful? Try these tricks:

1. Ask “Why?” After Voting

Don’t just move on—invite people to explain their votes.

“Why do you think I’d be most likely to get lost in my own neighborhood?”
That one answer might lead to a whole story—and probably more laughs.

2. Use Follow-Up Prompts

After someone gets voted, keep it going with:

• “Has that actually happened before?”
• “Do you see yourself doing that in the future?”
• “What would it take for you to actually do that?”

3. Let People Pass or Add Their Own

Some folks warm up slower. Give them the option to pass, or better—invite them to add their own question when ready. It’s a great way to get everyone involved at their own pace.

4. Build a “Get to Know You” Question Set

Use or create a version of the game focused more on curiosity than comedy. Some favorites:

• Who’s most likely to remember everyone’s favorite coffee order?
• Who’s most likely to try something new just to see if they like it?
• Who’s most likely to ask the best questions in conversations?

(Pro tip: We can help you create your own printable version!)

Conversation-First Question Ideas to Try

Here’s a quick list of questions that are perfect for starting real chats:

• Who’s most likely to change careers three times and still love what they do?
• Who’s most likely to move to a new city without knowing anyone?
• Who’s most likely to secretly write a book one day?
• Who’s most likely to spend a weekend without their phone—and enjoy it?
• Who’s most likely to give life advice that actually works?

Keep the Vibe Comfortable, Not Cringey

The goal is to connect—not to embarrass or corner anyone.
Here’s how to keep things light and welcoming:

• Skip anything too personal with new groups
• Avoid inside jokes if not everyone’s in on them
• Read the room—if someone’s quiet, pivot to more open-ended questions

The best WML game nights are the ones where people leave feeling closer, not exposed.

Final Thought: Small Questions Lead to Big Connection

You don’t need deep heart-to-hearts to get to know someone—you just need the right kind of questions that make people feel seen and heard.
“Who’s Most Likely To” does exactly that.

So next time you’re sitting across from someone new, hanging with a group for the first time, or looking for something better than “So… what do you do?”—you know what to play.