7 Tips for Coaxing a Shy Person Into a Conversation That You Can Both Enjoy

You might be familiar with the brick-wall effect: You go to chat with a stranger or even a friend or loved one only to find that no matter how many topics you might tap from your conversation-material arsenal, you can’t get a peep out of them. But while your typical conversational strategies might not draw this shy person out of their shell, that’s no reason to give up hope of ever connecting. Assuming they want to engage, figuring out how to talk to a shy person simply involves making them feel extra-comfortable in the situation at hand.

To first determine whether the person actually does want to engage, clinical psychologist Aimee Daramus, PsyD, suggests testing the waters with some gentle conversational prodding. “Start with something light about a topic that you two might have in common, then scan their face and body language,” she says. If they step back, stay angled away from you, or refuse eye contact, let it go; but if they turn toward you, look at you, or open up by un-crossing their arms or relaxing their posture, consider it a green light to move forward with additional chitchat.

“Start with something light about a topic that you two might have in common.” —Aimee Daramus, PsyD

As you continue to engage, however, it’s best to do so with extra care for how the shy person might perceive the situation—so that things don’t get cut short. Below, experts walk through strategies for how to talk to a shy person with ease and keep the conversation free-flowing.

Exactly how to talk to a shy person, according to psychologists

1. Make room for them to speak.

Your first inclination may be to fill the silence left by a shy person’s hesitancy to contribute. But while it’s certainly helpful to guide the conversation, it’s important not to confuse that intention with permission to fully own the interaction. “The more you take the responsibility of filling the conversation, the less the shy person will feel the need to step forward,” says clinical psychologist Chloe Carmichael, PhD, author of Nervous Energy: Harness the Power of Your Anxiety.

While it can be helpful to think up a couple conversation starters to have at your fingertips, resist the urge to charge ahead from topic to topic if the shy person doesn’t seem to dive in. “Instead, silently count to 10 after you’re done speaking so that it’s clear you’re interested in their thoughts, too,” says Dr. Carmichael.

2. Ask open-ended questions.

Questions that have a ‘yes’ or ‘no’ answer tend to elicit just that and not much else from a shy person. Leading with ‘how’ or ‘why’ questions, though, naturally encourages more dialogue, says Dr. Daramus.

Specifically, these types of questions often lead to more follow-up questions, which you can uncover through what Dr. Carmichael calls reflective work. “Start by loosely summarizing what a person said back to them, and then pause and ask, ‘Is that about right?’ or ‘What am I missing?,’” she says. “Or, you could even take them back in time with questions like, ‘Have you had that experience before?’ or ‘What do you think led up to that?’”

3. Match their conversational vibe.

Because familiarity tends to breed comfort, you can also try giving back whatever it is you’re getting, says Dr. Carmichael. That is, if you’re getting only two-word answers, try giving short answers in response, as well. While it might seem like this would limit the conversation, it can actually have the opposite effect of readjusting the level of responsibility that the other person feels, so that they’re more inspired to start giving (and, in turn, getting) more from your talk.

4. Mirror their body language.

Just as you might follow the shy person’s lead on the dialogue, you can also adopt a similar body positioning to theirs, says Dr. Carmichael. If, for example, they’re sitting curled up on a couch, you can put them at ease by sitting and curling up, too. “In this case, once you’ve achieved some synchronicity, then you might try to subtly open up your body a bit. And you might just find that they naturally do, too,” says Dr. Carmichael.

5. Narrate your experience.

If the conversation starts to skew a bit awkward, it may be helpful to quite literally talk it out. “You can say something like, ‘I don’t want you to feel like I’m just talking at you,’ or ‘I’d really like to hear what you have to say about this,’” says Dr. Carmichael. This serves the purpose of both illuminating any discomfort you may feel—the shy person isn’t a mind reader after all—and providing a little nudge of reassurance that they can feel comfortable offering up their viewpoint.

6. Engage a third element—whether it’s another person or an activity.

A one-on-one interaction may feel more intimidating than a group conversation, says Dr. Daramus, so, if you can, try involving another person or a couple of people. “Just be sure to ask the shy person’s opinion every once in a while, so they know it’s explicitly wanted,” she says. This will also keep them from getting lost in the group shuffle.

If you’re planning in advance, you can also take more of the pressure off the shy person by scheduling an activity around your conversation. A workout, art class, or event can act as something you two can bond over, and can also naturally provide a few topics of conversation in the moment, Dr. Daramus adds.

7. Know when to give it a rest.

If you can sense greater reluctance or nervousness at five minutes into the chat than you noticed when you dove in initially, it’s best to gently end the conversation with a pointed suggestion to talk later. “Find a reason that you’ll need to reconnect, such as asking for a recipe or the name of a song,” says Dr. Daramus. This way, your suggestion won’t feel like an empty promise.

Regardless of why the conversation ended or whether it happened sooner than you’d hoped, try to avoid construing the conclusion or the shy person’s silence as a personal rejection of you, says Dr. Carmichael. Instead, aim to replace that thought with a reminder to yourself that any good conversation is, at minimum, a two-way street—and, of course, it’s not possible to drive both ways at once.