Talking is hard! And while small talk is valuable, it only goes so far: Once you’ve gotten through commiserating over how “weird” the weather has been lately and swapping notes on Love Is Blind couples — in other words, once you’ve exhausted the socially accepted scripts for starting a conversation — how on earth do you maintain one? Sometimes a lull is the perfect opportunity to excuse yourself and head to the party’s snack table. But sometimes, for whatever reason, you want or need the conversation to continue. And what about when you’re texting? The inability to read body language and facial expressions can make those emoji-laden conversations especially challenging to maintain.
Whether you’re stuck in an elevator with a stranger, determined to connect with a crush or a new colleague, or just hoping to deepen your conversational abilities beyond pleasantries, we spoke to experts in conversation-making to help you move smoothly past a mid-conversation silence.
1.
Look alive — and interested.
Nothing kills a conversation faster than a face that says, “I’m waiting for this conversation to end so I can go do something else.” Make sure you look alert and interested. There’s no need to give off staring-contest energy with your eye contact or nod vigorously unless you really mean it, but you should be generally looking in the direction of whoever you’re talking to and reacting to what they’re saying. Definitely don’t scan the rest of the room over your conversation partner’s shoulder or turn at the slightest movement in your peripheral vision, and — as Susan RoAne, speaker and author of What Do I Say Next? told the Cut — don’t check your phone, even if you just got a text: “Because your message in that situation is, Oh, I don’t even know what this is, but it’s more important than talking to you.”
2.
Make use of small talk.
Small talk has a bad reputation, but it can both keep a conversation going and lead to bigger things. “We have to earn the right to have deeper conversations,” RoAne told the Cut. “And we do that through having had enough little conversations that connect us and make us feel comfortable with each other.” Don’t be afraid to talk about the news, what your plans are for the weekend, and the things you do for fun — it may spark a curiosity about your passion for bird-watching or their extensive knowledge of the LOTR universe. Follow-up questions are your friend, especially if you want the other person to be. “There’s a difference between the questions that people ask simply because they want to keep the ball in motion versus the questions that they ask because they’re interested to hear the answers from someone,” says Sheila Liming, writing professor and author of Hanging Out: The Radical Power of Killing Time. “One thing I love, when I’m getting to know people, is when you stumble upon that thing that you can tell somebody’s really, really on fire to talk about and go with it. Everybody’s got one; sometimes you just have to feel around a little bit until you get there.”
3.
Know the difference between vulnerability and oversharing.
We’re in a relatively pro-vulnerability age right now, and dropping your social façade for a moment to share that it’s been a tough week or to check in on how your conversation partner is really doing can be a valuable way to deepen your connection and create a more nourishing conversation. Just don’t take that as an invitation to get into the weeds of your relationship with your mother or offer a detailed recounting of your most recent breakup. You might think that getting super-personal super-quickly is an exercise in radical vulnerability — which, okay, maybe — and a way to get the other person to feel safe getting personal with you, too. But it can backfire spectacularly. Christopher Gottschalk, author of How to Start and Make a Conversation, warns that “more often, unfortunately, this results in your getting too personal before the other person is comfortable with you.”
4.
If you’re texting, be direct.
Communicating over text can bring up a whole minefield of conversational challenges: Are they slow to respond because they don’t want to talk to you, or are they just busy? What is that emoji supposed to imply? Are they ending a text in a period because they want you dead? Moe Ari Brown — an LMFT certified therapist, public speaker, and the love and connection expert for Hinge — says that we can think of things like emoji use, punctuation, message length, and response time as “digital body language.” It’s something to be aware of, for yourself and the person you’re texting, but not necessarily the be-all and end-all. If they’re taking a while to respond, “they may be at work, dealing with a family matter, working out,” says Brown. “Don’t take it personally or as the ultimate sign that they’re completely disinterested.”
Instead, says Brown, give the other person time to reflect and respond, and consider your own side of the dialogue. “We often try to convey emotion without actually using emotional language to do so,” they say. “If you’re feeling happy and want someone to know, rather than relying on digital body language, you could directly say, ‘I am so happy to hear from you.’” The same goes for dealing with perceived disinterest or confusing one-word replies. Over text, it’s worth letting the person you’re speaking to know that you’re feeling confused or uncertain. The worst they can do is ghost you!
5.
Listen actively.
Make sure you’re really listening to what the other person is saying, rather than just waiting for your turn to talk. What do they seem to be interested in? What do they want to talk about? “Instead of coming with an agenda, listen to what someone is enthusiastically talking about and ask a question about it,” RoAne says. It can actually be very difficult to turn off your inner monologue, about what you want to say next or where the conversation is going, and truly hear what the other person is trying to communicate. Pretend you’re a translator who needs to interpret someone’s words as directly as possible, and see if it changes the way you listen.
“When you listen actively,” Gottschalk writes, “you are signaling that you are taking the conversation and the other people in it seriously. They will participate more in the conversation as a result, and everyone will benefit.” Brown says active listening means being intentional in your communication, with the goal of mutual understanding. They recommend reflecting back what you heard the other person say to make sure you’re getting it right, for example.
6.
Ask open-ended questions.
Don’t fall into the trap of asking a series of yes-or-no questions. This makes it too easy for the conversation to stall, and too easy for your conversation partner to feel like they’re being quizzed. Instead, focus on open-ended questions. Debra Fine, author of the Fine Art of Small Talk, recommends the question “tell me about you,” because it allows the other person to take the lead, decide what they want you to know, and go from there.
This can lead to what Gottschalk calls the “ripple theory of conversation.” Like the ripples that occur when a rock is tossed into the lake, take their conversational cue and let it lead to something broader, and something broader, and something broader. For example, if you’re talking to a co-worker, maybe you can talk about her specific job, then the company, and then the industry as a whole.
7.
Lean into the icebreaker mentality.
Icebreaker games and questions are often hated upon, but let’s be real: How else would you get the opportunity to tell someone that you were born on a farm in Canada or that your uncle’s cousin is Mo Rocca? When a conversation is really faltering, it’s time to pull out the icebreaker questions. It’s a good idea to have a few standard conversation-revivers in your back pocket. You can keep it simple by asking about someone’s astrology situation or a little-known fact about them. But I recommend getting creative. Liming has a few icebreakers she likes to lean on: “Asking for their top-five favorite movies or their favorite breakfast cereal,” she says. “Something I really like to ask people about, I’m like, ‘Tell me about your favorite T-shirt.’ Everybody has one.”
Brown agrees it’s a good idea to ask questions that are more likely to inspire a story — instead of something like their favorite color, for example, ask what they were like in high school. The best questions are the ones you actually want to know the answer to. Brown likes to ask questions about travel and live-music experiences, and also recommends having a good supply of hypotheticals, like, “If you could only choose five ingredients to cook with for the rest of your life, which would you choose?” Avoid judgment and stay curious.
8.
Use the silence.
Sometimes, the best way to get someone talking is to let them linger in their own discomfort with silence. It’s a popular trick with journalists and teachers, but if you’re brave, you can use it in your conversations. Liming uses it in her classroom and finds it often leads to fruitful commentary. “Count to seven in your head, and wait for somebody to volunteer to fill the silence,” she says.
Even if your conversational partner doesn’t immediately rush to fill it, a moment of silence can be an opportunity in a different way: “Take a pause, take a breath, be okay with the silence, and return to the present moment,” says Brown. “How do you feel?” In a flirty context, Brown says you can “fill” the silence with a smile or intentional eye contact. And whether you’re flirting or not, you can also take a moment to observe the environment you’re in — “That’s such a great lamp, isn’t it?” — or even, Brown says, your internal environment. “Say out loud, ‘I’m at a loss for words. I’m enjoying myself so much, I don’t actually know what to ask you.’” Revealing your own fallible humanness is generally a good way to connect with another human.
9.
Ask for elaboration.
Half the time, especially in a conversation with someone new, we find ourselves talking just to talk, repeating standard talking points and saying things without totally even knowing what we mean. One good way to keep a conversation going is to simply ask “Why?” or “What makes you say that?” or “What do you mean?” The key is to ask with genuine curiosity, not as a gotcha. Often, this will get someone reflecting on what they’re actually trying to say, and result in a more interesting conversational path.
10.
Do your homework.
Gloria Hortua, the general manager of [salon]718 and a licensed cosmetologist and aesthetician, has perfected the art of keeping a conversation going over her 30-plus-year career as a hairstylist. She says that 75 percent of a hairstylist’s job is about engaging with a client. “What I learned at a very young age is that I have to learn a little bit about music, a little bit about art, a little bit about fashion,” she says. Lifelong learning is something she’s always valued, but she says it’s especially helpful in the beauty business, where picking up tidbits of knowledge outside her purview can help spur connection with someone new, and staying up-to-date on the latest trends in her field, thanks to her salon’s continuous educational programming, means she always has new information to share with interested clientele. “You have to prepare yourself,” she says. And while learning is worth it just for the sake of learning, perhaps the possibility of being an entertaining party guest will help motivate you to actually read the placards next time you’re at a museum.
11.
Expand your interpretation of a conversation.
What if “keeping the conversation going” isn’t continuing to say things in the moment, but is about continuing your connection with someone beyond an initial conversation? “Sometimes you just catch people on off days,” says Liming. “I try to respect that and catch them under different circumstances another time.” Maybe in your brief interaction, they mentioned an interest in college basketball but didn’t want to elaborate that day. Next time you see them, let them know you caught a game and see if their response changes. If you want to keep talking to someone, create the opportunity to do so. “I like to create open endings that themselves lead to future opportunities for interaction or conversation,” says Liming. “Like, ‘Hey, let’s do this again sometime’ or ‘I’ll see you next week’ or whatever.” She recently met someone at a party who she learned, through their conversation, went to the same gym as she does. Now, Liming has a new semi-regular gym buddy. “It was a way of creating a rhythm for us so we get to see each other and aren’t just waiting for circumstances to bring us together.”
12.
Practice makes progress.
Social anxiety can make the stakes of any conversation feel extremely high. Actively remind yourself that it’s just one chat, and even if it goes horribly wrong, you’ll have many more conversations in your life. Some will go well; others won’t. Regardless, you’re someone worth talking to, just like whoever you’re engaging with is. Even if you’re not naturally gifted at conversation, as long as you remain kind and interested, your conversation partner will likely leave with a positive impression. Like anything else, becoming a skilled conversationalist takes practice.
Liming, who quite literally wrote the book on connecting with people organically, says she’s a big believer in practicing conversational skills. “They’re something that I’ve had to self-consciously think about and practice over the years,” she says. “If you find that you’re not necessarily interested in this person that you’re talking to, or interested in whatever they have to say, you can kind of turn the interest back on yourself and think about, like, What’s good for me to know, or to learn, or to practice?” Learning that you’re not the best at relating to a particular person might encourage you to find strategies for dealing with that type of person more generally. When each conversation you have is an opportunity for reflection and growth, the dialogue never truly ends.