How To Make Friends in a Room of Strangers

Put an introvert in a room of strangers, and you just might have the room’s greatest conversationalist. I know it’s true, because I’ve proved it for 29.5 years now. It started with my Dad’s one good piece of advice. This is how I learned to make friends.

  • Do you want to make friends more easily?
  • Are you an introvert who wants to feel more comfortable in crowds?
  • Do you have kids that want to be more social–without being the patsy to bad influences?
  • Do you want to be the room’s greatest conversationalist?

. . . if so, carry on, wayward son.

I recently photographed two delightful, intelligent, beautiful sisters (pictured here). During our session the conversation somehow turned to friends, making friends, etc. I then found myself relaying the advice I’ve shared scores of times. [Old men like me shamelessly, obnoxiously spew unsolicited advice. And we yell at kids to get off our lawns.] The wisdom isn’t original with me; it actually came from my Dad. I’ve since learned that he stole it from Dale Carnegie.

I first heard the advice as an awkward 16-year-old 10th-grader. Now, as I share it with you, I’m an awkward 45-year-old 39th-grader. Progress.

I was deathly shy as a kid; painfully shy through Elementary and Jr. High. I had very few friends because I was afraid to talk, afraid to look like a doofus (which I’ve since embraced), especially afraid of talking to girls (remnants of that remain). Approaching High School (9th grade), I started to come out of my shell, engage with others, and assert mitigated doses of leadership. This led to a tremendous surprise my 10th-grade year.

My High School Counselor called me to her office. She explained that she’d chosen me to attend the Hugh O-Brian Youth Leadership Conference. I’d be staying a weekend in an out-of-town hotel with several hundred other students–one from each school in the state. She then confirmed that yes, the conference was free. And yes, I’d be required to miss a Friday of classes.

Miss a day of school?! I suddenly felt very, very leader-ish. And then I thought,

“. . . wait. I’m the ONLY student from my school?” Then,

“. . . wait. I don’t know ANYONE from any other school in the state!”

I’d mingle among hundreds of people . . . alone. Stomach suddenly felt sick.

Despite the fear, I attended (remember–day out of school). By the end of the conference, I’d made several friends, got along swimmingly with my roommates, and even found myself among the final 5 male candidates to attend the national conference [I wasn’t selected]. Yet when I arrived, as expected, I didn’t know anyone. No one. Not one soul.

How did I navigate so well? Hint: I DID NOT magically transform into the bigger-than-life, outgoing, middle-of-the-party guy. Sadly, John Hughes was not directing the story of my 1980’s childhood. Dang.

Enter my Dad’s advice. He died 2 years ago. Looking back, I remember only two profound (positive) things he ever said to me. This is one of them, and the only time I remember him directly giving me advice. It served me well at the HOBY Conference, and I’ve since embedded it into my DNA. He delivered this after I’d told him about the conference, and confessed that I was nervous.

“If you want to make friends,” he said, “do 3 things.”

  1. “Smile often. People are attracted to people that are smiling.”
  2. “Use the other person’s name in conversation. A person’s own name is the sweetest sound they’ll ever hear.” When you first meet them, repeat their name. Then say it again soon thereafter. Then say it when you end the conversation. [I’ve since learned that it’s important to use the name at least 3 times–it helps ME to remember it.]
  3. Talk about the other person. Everyone loves to talk about themselves, and it’s the only subject where they’re truly the expert.” [This, Friend, is the golden ticket! If you remember nothing else, this is the one!] This is the solution for the person who says, “But I won’t know what to say!” That’s fine! Don’t talk, ask questions instead.

For whatever reason, I took his advice . . . and it worked. I walked into a conference of strangers–a challenge for an introvert–and left with several friends. The same scenario played out as an adult. I moved from Little Rock to the Atlanta area. No friends, no contacts. A new job–the only Salesman of a new business . . .  business-to-business sales, a job that required that I find strangers that needed what I was selling. I scheduled myself at countless networking events . . . and did everything that I learned in the 10th grade. And it worked.

Here are a few things I’ve learned in the 29.5 years I’ve been doing this . . .

  • If it sounds difficult, fear not. It gets easy. It quickly becomes ingrained.
  • The best conversationalist in the room IS NOT the person with the best jokes, witty comebacks, and great stories. The best conversationalist is the person who helps other people talk. And they need help!
  • If this formula seems fake, contrived, or insincere, it is–if you don’t really care about the other person. If you are actually interested, it’s a simple tool that slices through inane small talk.
  • “How do you actually, physically walk up to a stranger and start conversation? Do you know what you’ll say?” Yes, I do know. When I’m scared to walk up and break the ice, I force myself to just do it. I walk into their space (where one of us HAS to speak), stick out my hand, and say, “Hi, I’m Bill. What’s your name?” That is literally the only thing that I know I’ll say–nothing else. However: 1. I’m smiling when I do it; 2. I repeat their name; 3. I ask them about themselves. I’ve learned that everyone else is just as nervous, and they’re grateful when someone else does the approaching.
  • Learn to ask “good” questions, not “bad” ones. This is simpler than you think. A “bad” question requires a one-word answer. A “good” question requires more. For example: “Cynthia–do you like Mexican food?” She answers “yes” or “no.” One word answer=bad question. “Cynthia–what is one of the best meals you’ve ever had?” Now Cynthia thinks and responds with more than one word. More than a one word answer=good question.
  • Just as there is “one Ring to rule them all,” there is one question to rule them all: WHY? Always ask why, then ask it again. So when Cynthia tells you about her favorite meal, you ask, “Why is that one your favorite?” Maybe she explains the place where she ate it/the people she was with. “Why is that special to you?” WHY? is always the best question to ask. WHY? is always the best question to ask. WHY? is always the best question to ask. I promise. Don’t forget it. I’ll repeat it again if I must: WHY? is always the best question to ask.

“A man wrapped up in himself makes a very small bundle.” -Benjamin Franklin

EVERYONE HAS A STORY TO TELL. And they want it to be heard. Embed that into your soul: Everyone has a story to tell! And they want it to be heard. They just need someone that invites them to tell it.

How do you empower others to tell their stories? How do you become the best conversationalist in the room? How do you make friends with strangers?

Two words answer those questions. Two words summarize everything I’ve written here. Two words have changed my life for the better:


Smile often. Use the other person’s name in conversation. Talk about the other person. Three tips to help you LISTEN WELL.

Now get out there, keep your mouth shut, and listen, you awesome conversationalist!

-mr. bill

FOOTNOTE: Introversion and Shyness are NOT the same thing. I’m not shy anymore, but I’m still an introvert (leaning towards ambivert). If you’re nerdy like me, and interested in the difference between shyness and introversion, CLICK HERE to learn more. If you like the article, Susan Cain is the super-brain who wrote it, along with the Introvert’s manifesto. Grab a copy below. And you can also grab Dale Carnegie’s life-changing book. Enjoy!


*Required legal speak: These are affiliate links. Should you choose to buy from these, I will receive a small percentage at no extra cost to you. Please and thank you.

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