How I Approach Strangers Without Being a Creep

Matt Bilotti
Matt Bilotti



I'm at an event. I don't know anyone here. I'm standing by the food to make it look like I'm thinking about what to eat. I'm trying to look like I'm too cool to talk to anyone.

Really, though, I'm secretly hoping and waiting for someone else to come and say hi. 

There's many articles online about how to "work a room," but they all advise the same thing: Break out of your comfort zone. This typically comes paired with a graphic like so -


But hardest part isn't getting out of your comfort zone; It's knowing when it's appropriate to join a group of strangers without being that person who suddenly initiated an awkward silence.

As uncomfortable as it may feel, there's really no way to avoid wandering around the room for a bit while feeling like that creepy dude or dudette lurking. I've picked up a few tips to keep myself from looking suspicious when I wander: 

  Keep a drink in your hand - even if it's just water. 

  Listen carefully while casually strolling through groups. 

  Walk slowly to get a gauge on what's being discussed.

While walking by slowly a few feet away from a group, I give myself at least 15 seconds to gauge their conversation. Within these 15 seconds, I look for any of the following five signals that it's okay to start talking to one or all of the folks in the group. 

Signal 1: Someone is bored or ready for an escape.


Is one of the individuals in the group glancing off into the distance at least twice within that 15 seconds?

Are they a third or fourth person in the group and clearly looking in a different direction with the others?

This is the perfect opportunity to target this unengaged individual, make eye contact, and free them from their misery by smiling and introducing yourself. 

Signal 2: Someone is using drawn out words, filler words, or single responses.


There are a few words that, when used repeatedly, trigger that a conversation is ending - or at least that one person is done with it. Examples include ...

  • Mhhm
  • Yeahhhhh
  • True True
  • Cool ...
  • Yep
  • Yeah
  • Nice

Hear these words repeatedly? BOOM. Jump in. These people are done with one another, making it the perfect time to approach.

Signal 3: Someone has their feet pointed in another direction.


This may sound silly, but if somebody is standing in a group conversation but their feet are clearly pointed in a direction outside that group or the person they're speaking with, they are most likely ...

  • Not interested in what the other person is saying
  • Looking to move in that direction in the near future
  • Leaning up against something with swag - in which case, they might not be looking for any conversation at all.

Signal 4: Someone is taking deep breaths or nodding slowly.


If one person is ending their sentences with long, deep breaths, it generally means they're ready to move on. Beyond the big breaths, from my experience, nothing is as crystal clear as when someone is nodding their head slowly. This is typically a big sign that the individual is tuned out. 

I've found both these instances to be great opportunities to approach that person and spark a conversation. 


Signal 5: Someone is wandering around confidently looking for conversation.


When I notice somebody else is wandering around the room on their own or look like they're employing the same strategy as me, I try to intercept their path and make eye contact.

Sometimes they're hoping to find someone like me to chat with. Other times, they may have their own agenda that doesn't involve me. I can typically sense this when they don't return my eye contact and keep moving around. 

These five key signals come into play at every event I attend, resulting in at least five to six valuable conversations. No awkward introduction, no awkward interruption, just a natural start for both me and the person I'm talking to.

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