Striking up a conversation—especially with a stranger—is a lot like adding kindling to a fire pit and hoping it ignites. Choose the wrong starter, and the flame will fizzle out. But when you get it right, conversation and connection can spark.
Conversations play an essential role in our well-being. Having just one quality talk a day, especially face-to-face, can increase happiness and lower stress levels by the end of the day, research has found. You don’t even have to know the person. In one study, people overestimated how awkward deep, meaningful talks with strangers would be, and found that instead, these conversations uplifted them and made them feel more connected than they expected. Plus, asking questions makes people like us more, which can be a boon to self-esteem.
But what should you say to get more than a one-word answer in response? We asked people who excel at small talk to share their favorite conversation-starters.
“What’s the best dining experience you’ve ever had?”
Raele Altano, a communication coach in New York City, likes the “HEFE” approach to conversation-starters. It stands for hobbies, entertainment, food, and environment (meaning the setting you’re in). Those four universal pillars lend themselves to talking points in almost every situation, she says. Who doesn’t love chatting about food, for example? Asking about favorite restaurants “helps you learn something new and get to know them and their preferences,” she says. Altano recently asked someone about their best recent dining experience and what made it so great—and learned that the other person had traveled to Japan on their honeymoon at the same time she did for hers, and that they were at the same restaurant in Tokyo only days apart. That forged a bond they otherwise never would have known existed, she says.
“What’s been the best part of your week so far?”
Asking someone how they are is practically a reflex. Instead, switch things up by asking the next person you encounter about the highlight of their week, suggests Robin Shear, the Detroit-based author of Messy Joy: How Joy Can Begin Before Your Difficulties End. “People are caught off guard because they’re surprised someone cares enough about them to ask,” she says. “They’re usually jolted out of the mundane and suddenly feel important.” When she asks people this question, she typically finds they have to pause to consider it—and they then tell her that they’ll have to think about the bright spots of their week more often. A grocery store checkout clerk, for example, recently told Shear about the weekly dinner she had just had with her son. By the end of the conversation, “We both had tears rolling down our cheeks,” she recalls. “I’ll never forget it.”
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“What’s a hobby you’ve always wanted to pick up?”
This question can spark fun and introspection, says Jenny Woo, who teaches emotional intelligence at the University of California, Irvine, and created 52 Essential Conversations, a social-emotional learning card game. (She also tried rock climbing recently for the first time, and loved it.) Don’t forget the built-in follow-up question, Woo advises: “What’s stopping you?” You’ll learn an interesting tidbit and might inspire your conversation partner to carve out time for a new interest.
“What’s the nicest thing anyone’s ever said about you?”
Every time Shear asks someone this question, they smile. “Every single person,” she says. Take this recent exchange at a fast-food joint: The guy waiting on her lit up and said, “Someone once told me I’m a people person.” That led to a conversation about how he might use his people skills in the future, and his hope to eventually become a teacher. “I thanked him for being the best part of my day,” Shear recalls. And, by the way: The nicest thing anyone ever said about her came from her daughter, who told her, “You know how to make people feel like they matter.”
“Do you have any recommendations for good books, podcasts, or TV shows? I’m looking for something new to start.”
When Jessica Hunt, a therapist in California, wants to instigate a conversation, she asks the other person to share what they’re reading, listening to, or watching. “It’s straightforward yet remarkably effective,” she says. Plus, it’s versatile and almost always appropriate. It also shows genuine interest in your conversation partner’s preferences and opinions, and offers them a way to showcase parts of their identity, personality, and beliefs. Ask Hunt for her favorite recommendations, for instance, and she’ll tell you she loves listening to Up First from NPR, The Mom Hour, and the interior design podcast The Great Indoors. The question “reveals so much about someone’s inner world without being intrusive,” she says.
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“Would you rather be a time traveler or a mind reader?”
You read that right—and your reaction is exactly why Tenyse Williams likes this question. “It alway grabs people off-guard,” she says. Plus, it requires imagination, curiosity, and introspection; not to mention, it’s fun. Williams, who’s the founder of a marketing agency in Brooklyn, once asked a chef this question during a large speaking event. After thinking it over, the woman responded: “Definitely a time traveler, to snatch all the historic recipes before anyone else.” The room dissolved into laughter, and the lighthearted moment buoyed the rest of the evening.
“What’s the most interesting thing you’ve learned recently?”
This question is open-ended and inviting—and can lead to fascinating follow-ups, says Erica Thomas, who hosts supper club events in Atlanta and is the founder of the website Eating With Erica. “It works wonders at networking events, parties, and even when you’re simply chatting with friends or acquaintances,” she says. Thomas especially likes that it draws people into discussions about their passions and curiosities, helping foster an exchange of ideas. When she used it at one of her dinner parties, for example, it prompted a discussion about travel to Europe—which led to deeper conversations about life lessons, change, and spontaneity.
“That belt pairs so nicely with your outfit! How did you learn to be so creative with your accessories?”
Everyone loves a compliment: Research suggests receiving praise is as thrilling as a monetary reward. That’s why Jillian Amodio, a licensed social worker in Annapolis, Md., starts conversations by dispensing kind words, followed by a relevant question. Tried-and-true favorites include: “I love that shade of blush. Where did you get it?” and “You’re great at your job. Is this a field you’ve always wanted to be in?”
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Amodio, who teaches career development at Anne Arundel Community College, will sometimes use this line with her students: “You’re always the first to offer an answer in class. I admire that about you! Have you always been this outgoing?” Offering a compliment helps people “feel seen and valued,” she says—and following-up with a question ensures a more expanded conversation than a simple thank you or smile.
“If you could do anything you want without having to worry about money, what would you want to do and why?”
Ah, the million-dollar question. We all squirrel away dreams of what we’d do if we suddenly came into a lot of money, Woo says, and this wording gives people permission to set aside real-life concerns and keep things fun and upbeat. “It provides a wide canvas for the person to illustrate their dreams and aspirations,” she says. Woo recalls using this question as an icebreaker, and noticing the room became louder and more lively with laughter. People discovered they shared common interests—there were even aspiring magicians in the room—and found each other afterward to chat more.
“What’s your perfect Saturday?”
People seem to enjoy answering this question, says Meg Irvin, who works at a communications firm in Richmond, Va. If they turn it around and ask her about her perfect weekend, she tells them she has two young kids, so “sleeping in sounds pretty glorious.” Also on the docket: popping into a farmer’s market, taking a walk in the sunshine, and maybe checking a day trip off the running list of destinations she keeps on her phone. Who knows? Maybe you and your conversation partner will make plans to share a Saturday activity together.
“How would your best friend introduce you?”
Ask Jenn Whitmer this question, and she’ll tell you her BFFs would describe her as bold, energetic, and expressive. “Full of joy and ready to give that to others,” she says. You might also learn that she’ll break into song at the drop of a hat and has a contagious laugh. Whitmer, a St. Louis-based keynote and TEDx speaker who hosts the Joyosity podcast, likes this question’s revealing nature, and the way it demonstrates a genuine desire to learn about the person you’re talking to. “Stories come out, and the follow-up questions are so easy because you’re connecting over something real,” she says. “Most people dread small talk because it feels meaningless or transactional. People want someone who’s actually interested in them as a human.” Asking great questions—and listening to the answer—can help anyone master the art of conversation, she says.
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