How To Talk To Someone Who's Shy, Quiet, Or Less-Social
Most of this site has been about how shy, less-confident people can improve their social skills and ability to get along with others. But it cuts both ways. Some more-outgoing people could stand to brush up on the way they act around their shyer, quieter, or less-naturally-social peers. If you're more of a chatty, self-assured, social butterfly type, here are some ways to relate to people whose confidence or conversation skills aren't the same as yours:
Do what you can, but accept you may not be able to have the kind of conversation you want with someone who's shy or less-social
Some shy people are a bit withdrawn at first, but open up before long. Others are at a point in their lives where they're too nervous and inhibited to have a flowing conversation with someone they just met, and no amount of consideration or social savvy on your part is going to change that. Someone else may be in a less-social mood, and not feel like talking no matter how much you try to meet them halfway. Remember you're never 100% responsibile for how an interaction goes. Everyone in it has to do their part. Try your best to make people comfortable or adjust to their style, but don't feel you did something wrong if it doesn't work out.
Don't take their quietness personally
I think every shy or quiet person has had the experience of other people getting annoyed at them because they were reserved and untalkative. That's just what they do though, they hang back and don't speak as much. It's not because they're mad, or snobby, or that they're purposely trying to kill the fun vibes in the room. They're just a bit tongue-tied at first and need some time to warm up to the people they're with, or it's their natural style to sit back and observe.
Don't comment on how shy or quiet they seem
Shy and quiet people hate this. Sometimes someone will call out their quietness in an accusatory, confrontational way. At other times they're more well-intentioned and matter-of-fact. Someone might make a comment to the group in front of them, like they're not there ("This is Craig. He's nice, but kind of quiet.")
Either way, it's kind of thoughtless and annoying. Don't say stuff like that out loud. Also, rather than shaking them out of their quietness, it often makes people feel more self-conscious and misunderstood. Oh, and never, ever comment on someone's shyness like they're an adorable, shivering little lamb. Like, "You're shy? Awwwww!"
Take the lead in the conversation, but don't overdo it
If you think someone is being less-talkative because they're feeling shy and can't think of what to say, it can help to carry most of the weight in the conversation. Before long they may start to reciprocate more.
But all this applies only to a point. If someone doesn't seem like they want to talk to you after a few minutes, or they're not contributing at all to the discussion, then give them their space and back off. No point in pulling teeth, or bombarding them with verbiage, when the other person wishes you'd leave them alone. They may simply not feel like being chatty at the moment.
Another problem is that if you take the lead too much you the other person may technically have a conversation with you, but they're not enjoying or contributing to it. Instead they feel like they're being railroaded along by your questions, which they're answering out of politeness.
Give them a few minutes to warm up to you
This is related to the point above. When a shyer person first has to talk to someone, they often feel anxious and put on the spot. They may also be a bit defensive and put up barriers. After a few minutes the anxiousness and cautiousness can fade and they'll start to open up. Sometimes all you have to do is wait a bit for their discomfort to dissipate. And again, don't take it personally if they don't seem warm and loving at first. Their nerves may just be making them tense.
Give them time to respond to you
If someone is really good at coming up with things to say a mistake they can make is they'll ask a question or make a statement, and when the other person doesn't respond instantly, they say something else to fill the air space. Their conversation partner could have responded if they were just given a few more moments to put their thoughts together, but now they feel dismissed and steamrolled.
This point is admittedly tricky to apply because it depends on who you're talking to. More thoughtful, slow-to-respond types will appreciate you giving them some breathing room. However, it may make more-shy individuals feel on the spot and worried about creating an awkward silence when they can't answer you right away. If you get the sense that's the case, it's okay to say something yourself and bail them out.
Be wary of topics they may not be comfortable with
Not always, but sometimes shyness or a more-solitary nature can accompany things like being romantically inexperienced, or not having a ton of friends. Someone in that camp may wince when people ask them things like, "What are your buddies up to tonight?" or "How are the ladies treating you?" or "What did you do this weekend?" If you have a feeling someone might fit this description, then steer clear of talking about these things. The topics will come up eventually anyway if they're comfortable with them. If not, then you've helped them save face.
Try to hit on a topic they want to talk about
Shyness makes it harder to think of things to say, but most people have an easy time talking about topics they're interested in. Like if someone likes video games, all you have do is say Nintendo or roguelite and a dozen things will come to their mind. Try to land on one of those interests, and they should have a much easier time speaking with you.
Avoid the usual small talk as much as possible
Shy, quiet people say this all the time: It's not they hate the idea of conversation, but they prefer to discuss deeper, more-interesting topics, not yak about the weather or sports just for the sake of speaking. They don't have as much patience for that kind of thing. When you first start speaking to them a bit of small talk may be unavoidable as you cast around for a topic they want to speak about. Once you hit on one, it's okay to get more in-depth.
Don't panic if there's the odd silence while talking to them
This article goes into more detail about how to handle awkward silences, but basically you can usually get through it if you don't make a big deal out of them, and just start a new conversation thread, or take a moment to think of the next thing you want to say. If the conversation was winding down anyway, or they really seem like they don't want to talk to you, you can also gracefully use a silent moment as a way to wrap things up.
If possible, try to do an activity while talking to them
It takes the pressure off to keep a conversation going the entire time. You don't have necessarily have to set up an elaborate board game night. Even something simple like watching TV or walking around while you hang out can make things easier for them.
Be careful about playfully teasing them
Their insecurities, and possible history of being picked on, can lead them to take your joking remark the wrong way. If you want to poke fun at them don't say anything too cutting, and make it really clear through your body language that you're being friendly and affectionate. Be smiley and goofy, not dry and sarcastic.
Generally give them low-key positive feedback and reassurance
Don't be fake and overdo it, but try to communicate that you're friendly, you like them, and enjoy talking to them. Send out warm, interested non-verbals. Sincerely compliment them when it's appropriate, like if they said something funny or insightful. Shyer people can be quick to believe they're coming across as unlikable and boring. They're sensitive to signs other people are mean and rejecting. Let them know you're not thinking of them that way.
Try to set a frame that you don't expect your conversations to be dazzling and perfect
Shyer people can tell themselves they have to be amazing conversationalists or they may as well not bother. Help them remove that self-imposed burden. If it's believable, make an offhand remark about how you sometimes feel nervous meeting new people, or mingling at parties, or whatnot. If you happen to stumble over your words or your mind goes blank while trying to answer a question, be comfortable with yourself and laugh it off. Maybe comment that you can appreciate it when two people can sit in silence, and don't feel the need to have an instant reply to everything.
Don't be overly solicitous
Sometimes shyer people won't speak up when they want something from you. You can fall into the habit of asking them if they're okay every twenty minutes. "Are you hungry yet? You sure?", "What movie do you want to watch? You sure? Are you sure?" Even if someone knows better, they can still find themselves becoming too solicitous around their shyer friends. Don't do it. It gets old real quick. If they want something they'll ask for it. And if they don't, it's not your job to watch out for them.
If you want to do something with them assume you're going to have to ask
Asking people for certain things carries a risk of rejection and can be anxiety-inducing. Like a shyer person may hesitate to invite someone to hang out with them. So if you want something from them, assume you're going to have to be the one who asks. Don't wait for them to take the initiative.
Don't take it personally if they want to escape after spending a few hours with you
Less-naturally social people get more-easily drained by socializing and have to recharge their batteries by being alone. If someone's shy their nerves may have had all they can take after a few hours as well. Their friends may get confused or offending when they want to take off after "only" spending half the day with them. In the friends' minds it's only be natural to want to keep hanging out. It's nothing personal though. Some people are satisfied after a few hours of social time, and want to do something else after. It doesn't mean they hate you.
Don't take it personally if they seem to do something "insensitive" or "selfish"
First, what you see as "seflish" may be an Apples and Oranges situation. Like if someone wants to spend some time alone, that's just their preference and not a slight against you. However, if someone is shy, less-socially experienced, or they spend a fair amount of time alone and are used to doing their own thing, they can sometimes accidentally do things that truly hurt people's feelings. Sometimes their simple lack of knowledge about social rules causes them to make a blunder. There's no ill will behind it, they just didn't know any better. A shy person may make a social mistake because their nervousness is causing them not to be able to think straight, or they know what they should do, but are too inhibited to do it.
Finally, if someone is used to their own space, they may unintentionally come off as self-focused or like they don't care about other people. Like at a barbeque they may go inside to grab a drink for themselves, and not do the polite thing and ask if anyone else wants one too. Again, it's not that they actively dislike people. They're just used to only having to worry about themselves most of the time, and they forget to think of other people.
Don't be dismissive if they seem to dislike an outgoing person
Just because someone is outgoing doesn't mean they can't be off-putting in some ways. Sometimes they're cheesy and just a bit too much all around. At other times their chattiness is accompanied by interrupting, not giving other people a chance to speak, or only talking about what they want to discuss. But what happens when shy people seem annoyed at them? "Oh, well you're anti-social. It's no wonder you can't handle them." Yes, maybe some shy people do need a slightly thicker skin when it comes to tolerating outgoing types, but at the same time, don't write-off their legitimate opinions with, "Well you're quiet, so..." It's irritating and makes them feel misunderstood.