6 Sure-Fire Ways to Start a Conversation

6 Sure-Fire Ways to Start a Conversation

"How are you?"
"Good. How about you?"
"Pretty good."

Ok, now what do you say?

Focus on the person you want to speak with or focus on something you both share in common. Not only will he/she enjoy talking with you more, but you'll increase your chances of being liked as well.

Ok, how do you do that?

In this post, I'm going to show you 6 sure-fire ways to start a conversation. If you haven't read my post about greeting others with "How are you?" in the United States, you might want to start there first.

1. State the Obvious

While standing in the checkout line at Kroger, I watched the woman in front of me place 6 stacks of Visa gift cards on the conveyer belt –– valued at more than $1,300. "That's a lot of gift cards!" I said.

She smiled.

Sure, I had stated the obvious, but I could've done better. I could've stated the obvious by connecting it to her. I should've said, "You're going to make a lot of people happy with those gift cards."

When you state the obvious, make sure you've connected what's "obvious" to the person you're speaking with in order to increase engagement. To do this successfully, you might need to some additional information, but that information could be the difference between a smile and an engaging interaction.

Hiker: Tough hike, huh?
Stranger: [taking a deep breath] Are we almost there?
Hiker: Getting close.

Shopper: Gorgeous day, isn't it? We haven't had a day like this months.
Cashier: I hope it stays like this all week.

2. Ask a Relevant Question

I love Trader Joe's Popcorn in a Pickle! I bought a bag of this pickled-flavored popcorn last summer as an impulse purchase and it was surprisingly tasty. However, this summer I couldn't find any Trader Joe's. So, when I checked out, I asked the cashier when they'd have more Popcorn in a Pickle. He said that it was only available for a short period this year.

"It's strangely delicious, I said. "Have you had it?"

He told me that he loved pickles so much that he'd drink pickle juice from the jar, but for some reason pickled-flavored popcorn just wasn't for him.

Not only had I asked 2 relevant questions that led to a fun and humorous exchange, but I also got my answer. Unfortunately, no more Popcorn in a Pickle this year.

Employee: How are you?
Manager: Good. How was the meeting with the Nelson's yesterday?
Employee: Perfect. They're coming in today to sign the contract.

Senior Colleague: Are the roads still icy?
Junior Colleague: The salt trucks are just getting started. How long did it take you to get here today?
Senior Colleague: 40 extra minutes. How about you?

3. State an Interesting Fact

Did you know the green plastic stoppers that Starbucks uses to help prevent coffee from spilling while in transit are actually called splash sticks? I've heard cashiers and customers alike call them stirrers and stoppers, but when Starbucks introduced them in a 2008 blog post, they referred to the little green objects as splash sticks.

Older Cousin: [watching a relative grab a bottled water from the refrigerator] Did you know that men are supposed to drink 3 liters of water a day and about 2.2 liters for women?
Younger Cousin: Really? Where'd you hear that?
Older Cousin: I read it on the Mayo Clinic's blog.
Younger Cousin: We'd better drink up! Want a water?

Neighbor A: Hi Wendy! How's it goin'?
Neighbor B: How are you, Martha?
Neighbor A: Did you hear garbage day is moving from Monday to Tuesday?
Neighbor B: Really? From when?

4. Give a Compliment

My wife and I were out shopping recently when a woman we'd never met walked up to us. "Excuse me," she said to my wife. "I love your pants! Where'd you get them?"

A sincere compliment related to someone's style, skill or personality can feel awesome. Someone might remember a compliment for days, weeks or even years. Just make sure your compliment is sincere and appropriate.

Client: You're very creative. I love your designs!
Designer: Thank you! I'm so relieved to hear that.

Friend A: Hi Bill. Thanks for taking my call this late. I knew I could count on you.
Friend B: What's goin' on?

5. Say Something Humorous

When the barista and I overheard a mother sternly call her child by his first, middle and last name, I turned to her and said, "Do you the point of a middle name?"

She shook her head.

"So a child knows when they're in trouble."

She smiled and then told me what her mother used to call her when she got into trouble as a child.

Don't try to be a comedian, but when the opportunity presents itself for relevant, suitable humor –– give it a try. Everyone likes a laugh.

Dinner Guest: You must be Simon. I've heard so much about you!
Host: [smiling] I'll try not to disappoint. You're Grace, right?
Dinner Guest: [nodding and smiling] You've already met my expectations.

Passerby: [pointing to the dog] Is that an Akita?
Dog Walker: Yes. Do you have one?
Passerby: No, but I just watched a movie about an Akita with Richard Gere.
Dog Walker: Hachiko, right? How was that?
Passerby: I liked the dog.

6. Mention a Current Event

Have you finished your back-to-school shopping? Have you seen that new movie? How was the company picnic? What are you doing for Thanksgiving? Did you hear about the woman who won the Powerball jackpot?

We're surrounded by current events that compete for our attention –– news, entertainment, technology, sports, holidays, special occasions, annual calendar events, etc. Mentally bookmark the current events that are most interesting to you and probably others, too. Then, rely on them to help start a relevant conversation.

Friend A: What are you doing for the 4th (Independence Day)?
Friend B: We're going to run the AJC Peachtree Road Race. How about you?
Friend A: We're having a barbecue at the lake. Want to come after the race?

Customer: [watching the news on TV] Have you seen this commercial? Why would anyone ever use that medication with all those possible side effects?
Proprietor: No kidding! Saturday Night Live recently had a hilarious segment that made fun of these commercials.


You just learned 6 sure-fire ways to start a conversation. Keep your questions short, facts relevant, humor appropriate and compliments genuine. Enjoy meeting others and they'll enjoy meeting you, too!

Which one of these methods do you use most to start conversation? Can you think of any other suggestions? Answer in the Comments below.

6 Sure-fire Ways to Start a Conversation first appeared on the Culture Gaps Blog by Jeff Shibasaki.


Save to Pinterest


Jeff Shibasaki blogs about effective communication skills for the USA at Culture Gaps and healthy web design for unhealthy websites at Bento Sites.