Search Menu

Learn From My Mistakes: How to Successfully Talk to Strangers

Learn From My Mistakes: How to Successfully Talk to Strangers

Talking to a stranger is scary. They're a stranger. They could be anybody! A cunning pirate, a half human/half octopus sea witch, or  even (shutter) a mime. Even though you're more than likely NOT dealing with a Disney villain, most people are going to possess a natural amount of apprehension when approaching and conversing with unfamiliar people. But what if I told you there was a way I could ease that apprehension? I'm about to appease your conversational anxiety by teaching you my patented "Ice Breaker Method."

Now, when I say "Ice Breaker," I'm not referring to a sleazy way to talk to a member of the opposite sex. Nothing like:

Girl: "Hello handsome. How much does a polar bear weigh? Enough to break the ice. Name's Natalie. You want to come over to my place and watch a PG-13 movie with the lights off?"


Guy: "Sup. You like pants? Because I'm wearing pants. Name's Brian, but my bro-bros call me Wolfman. Let's close our eyes and cuddle.

No. No. And one more time with feeling: NO! I find pickup lines to be repugnant. I also find the word repugnant to be repugnant and that's why I used it to describe pickup lines. When I talk about conversational ice breakers,I'm referring to ways to charmingly  begin or extend conversation. We've all met someone new and exciting only to have the conversation stall. The scenario usually goes like:

Handsome Guy: Nice party, right?
Beautiful Girl: Definitely. I love the homemade Draco Malfoy piñata. So how do you know Jeremy?
Handsome Guy: We have AP Chem together. You?
Beautiful Girl: We have AP Lit together!
Handsome Guy: Cool
Beautiful Girl: Cool.
Awkward pause
Beautiful Girl: Well, I'm going to go jump around in the bouncy castle for a while.

And the relationship is over before it even began! It's a real shame, in my opinion, which is why I'm here to ensure that it doesn't happen to you. The below tips are going to be focused on talking to someone you're romantically interested in because, let's face it, we're all really just looking for a cuddle buddy. The best setting to showcase your  ice breaker prowess is at a social setting featuring a mixture of different groups of people. Chatting up friend of a friend is the absolute best way to meet new people. Hands down. It's how Romeo and Juliet met,and other than dying they turned out alright.

There are three stages to effectively implementing the ice breaker method. Do you have a pen and paper? Doesn't matter. You don't need one because you're reading an internet article.

Step 1: Introduction

Approaching a complete stranger is the second most difficult thing to do on the planet. The first? Anything involving fractions. (Seriously, can't we just round everything up to one?) The way I alleviate those pesky ol' nerves is by tricking myself into thinking I'm just asking a stranger a question. Listen, we're all in agreement that this sounds ridiculous, but it works. By convincing yourself you're merely asking a question, as opposed to attempting to flirt with someone, you swindle your brain into remaining calm. In your face, BRAIN! Google zebra ketchup toes. Alright, alright! Stop forcing me type nonsense, brain. I take it back.

Here is a real-life example from a birthday party I attended two weeks ago:

Josh: Excuse me, do you happen to know what's upstairs?

Girl Whose Name I Couldn't Hear (I think it was a color. Is "Mauve" a name?): It's a coat check room.

Josh: A whole room for coats? Seems unfair. Humans and coats shouldn't receive equal room. We outrank them.

Was that my finest hour? No. Are Mauve and I going to get married? Probably not, since I don't know her name, and she mentioned her boyfriend an estimated 12,000 times, but we did have a pleasant 20-minute conversation after our initial introduction.

Step 2: The Compliment

After the initial introduction, I tend to proceed with a compliment. Not in a duplicitous, phony way, but from a place of genuine sincerity. I tend to always compliment people on their scarves. Like, all the time. I think I just like the idea of warm necks, which is funny because I used to be very anti-scarf, but that's a boring story for a never day. Everybody loves a compliment. "I really like the color of your sweater"; "What a fun, quirky bracelet"; "I've noticed you have some extremely muscular elbows." Nope. Just kidding with that last one. Don't be Creep-ville 3000. Polite, sincere compliments help to create a conversational atmosphere of casual comfort. Your goal is to keep the conversation flowing and avoid awkward pauses.

Step 3: The Ice Breaker

There was a time when I didn't use ice breakers. I'd approach conversing with a stranger like an English Bulldog learning to walk. I'd meekly mumble hello while making minimum eye contact, then follow it up with a suave, easy-going inquiry like, "You have a name what?" The sole purpose of an ice breaker is to keep the dialogue progressing  in a natural way. You want to ask a question that will help create a fun conversation. For example:

1. What was your favorite school lunch?

2. If you could only read one book/watch one movie/enjoy one television show for the rest of your life what would it be?

3. Who would be on your "Celebrity Mount Rushmore"?

4. You're playing Paper, Rock, Scissors, and you and your opponent (a bullfighter named Kip) both played rock in the first round. What do you play in round two?

5. Which of the four Ninja Turtles do you most relate to?

The goal is to ask a question that can develop into a pleasant discussion. Try and steer the conversation towards something you're passionate about. I tend to chat about television, celebrities, and fun facts about pie-eating contests. Regardless, the most important thing to remember is to relax and be yourself. Once, while nervously attempting to ask for a girl's phone number, I asked her if she liked sneakers. Literally. I said those worlds to another human being I was trying to impress. I forgot the question I meant to ask and embarrassingly stuttered, "Do you like sneakers?" Turns out she did, but she had to pause our conversation to go to the bathroom. In another building. In Canada. When people ask "What's the worst that can happen?" they're talking about that exact moment. So go ahead and take a chance; just don't ask them if they like sneakers.

Do you have any favorite ice breakers? Who is on your "Celebrity Mount Rushmore"? Do conversations with strangers terrify you, or do you embrace the challenge with verve and swagger?

Topics: Life
Tags: guides, awkward situations, funny things, how to, dos and don'ts, ice breakers, making new friends, awkward conversations, learn from my mistakes, splogger series

Write your own comment!

About the Author
Josh Sorokach

Josh Sorokach is a comedy writer living in New York City. He's a former American Idol winner, three time Olympian, and habitual liar. Follow him on twitter @Joshsorokach.

Wanna contact a writer or editor? Email