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You’ve probably experienced this. You regularly see people at your local cafe, the gym or work, and you think you could be friends. But is there real potential there? Or are you just better off as nod-and-wave acquaintances?
I’ve spent the past decade researching and reporting on friendship, and I wrote a book about why friendships are struggling — even though it’s never been easier to stay in touch.
It’s hard to move beyond small talk when engaging with new people. Sticking to safe topics like the weather feels comfortable, but it rarely leads to real connection.
These four questions can reveal whether someone is interested in becoming more than just an acquaintance.
1. ‘Hey, I’m heading to [a fun activity] this weekend. Care to join?’
If you have plans like a restaurant opening or author talk, ask them to be your plus one. It’s a low-pressure way to see whether they’re interested in spending time together.
When you extend the invite, pay attention to their body language. Someone who’s excited will often smile, make eye contact or lean in. If they politely decline, don’t push it. Since you were already planning to go, there’s no awkwardness.
And if they’re interested but genuinely busy, they’ll often suggest another time.
2. ‘Tell me more about your favorite hobby. Any suggestions for a newbie just getting into it?’
Ask someone about a hobby they’re passionate about and what they’d recommend to a beginner.
If they’re interested in building a friendship, they will be excited to share what they love and want to hear about your hobbies, too.
For example, I’ve asked casual friends about their favorite band and which album I should listen to first. If they follow up with a link to a song or album, that shows that they’re open to a friendly exchange.
This is how common ground develops. And if the band comes to town, you have a natural reason to follow up and ask if they’d like to go together.
3. ‘What’s something you’ve always wanted to try but haven’t gotten around to yet?’
This question helps unlock your potential friend’s deeper desires. You’re giving them permission to share something personal with you.
This conversation can lead into many directions. You might even discover you can help make their dream come true: “You want to try every pizza in the city? My uncle owns a pizzeria in town. I know all the best spots!”
Friends need clear and compelling reasons to keep their bond active. What’s more compelling than meeting a goal? Maybe you two can even become accountability partners.
4. ‘What do you like to do in your free time? Anything you need help with?’
The follow-up of “Anything you need help with?” is what makes this question so effective. It encourages the other person to think about where your interests or skills might overlap with their own.
This is also a chance for you to broaden your community even further, especially if it’s a group activity they love. Maybe they need an extra member for their trivia group or another player for their softball team.
This is one of the fastest ways to get a sense of your chemistry. And if you have a shared sense of humor, similar values or common interests while working toward a goal, you’ve laid the groundwork for an enduring friendship.
Anna Goldfarb is a friendship expert and author of “Modern Friendship: How to Nurture Our Most Valued Connections,” a Next Big Idea Club Must-Read. She writes the Substack Friendship Explained. She’s been featured in the New York Times, The Atlantic, The Washington Post, WIRED, Oprah Daily, Goop and more. Follow her on Instagram.
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