• Franz Saint-Fleur

How to Start a Conversation: Creating the Perfect Icebreaker



It can feel awkward to chat up a stranger, but by keeping a few simple tips in mind, you'll be a pro in no time.

Be Aware of Your Surroundings

The best way to do this is by getting out of your head. When we’re caught up in our own stream of thoughts, conversation requires much more effort. When we get out of our head and pay attention to the present moment, we notice our surroundings—then we can free associate and find topics to talk about.

If you're in line at the store and the queue happens to be long, this presents a great chance to break the ice with people around you. Ask someone, "Wonder why the line is so long—is there a sale going on today?" Simple as that. I used this one today in a deli.

Be Observant of Other People

Look around at the people near you. Notice what they're wearing. Their height. Does it look like they work out? Look for as many details as you can—any one of these things can help you start a conversation. I always try to find at least three things about a person that I can talk about with them.

Ask Open-Ended Questions

Instead of asking a question to which someone could give a simple “yes” or “no” response, look for a little more detail. Don’t be too convoluted or too personal, but do be observant. Remember: details about a person can become conversation pieces.

When I look for three details about a person, I usually see their shoes, shirt, and phone. These things are easy to notice, and not overly personal or invasive. If I like any of those three things, then from there I can ask the following open-ended questions:

”Yo, nice shoes—where did you get them?”

“Hey—how do you like that phone?”

“Excuse me, that’s a nice shirt; where did you get that?”

Or if it’s a sports jersey, I might ask: “How are the (team name) doing this season?”

These tips are straightforward and easy to remember. Beginning a conversation with a stranger is usually the hardest part—but once you're talking, the door is usually open for more.

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