How To Talk To Someone Who's Shy, Quiet, Or Less Social
Most of this site has been about how shy, lonely people can improve their social skills and their ability to get along with everyone. But it cuts both ways. Some more outgoing people could stand to brush up on the way they act around shyer, quieter, or less naturally social types. I think it's important for people with different communication styles to meet each other halfway. Here are some tips:
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 ever comment on how shy or quiet they seem
Shy and quiet people hate this. Sometimes the person will say something in a more accusatory, confrontational way. At other times it's more well-intentioned and matter-of-fact. Sometimes they'll make a comment to other people in front of the person, 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 a cute, 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. After a few minutes that 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, for five minutes 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 towards the other person and put up barriers. After a few minutes the anxiousness and cautiousness tends to 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. It could just be a matter of their physiology being aroused...
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 partner could have responded if they were just given a few more moments to put their thoughts together, but now they feel ignored 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 save them.
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. They may cringe 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 anyways if the other person is comfortable with them. If not, then you've helped them save face.
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 since things to say are already in their brain ready to go. Like if someone likes video games, all you have do is say 'PlayStation 3' and a dozen things will come to their mind. So try to land on one of those interests, and they should have a much easier time talking to 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 teams 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 is 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 anyways, or they really seem like they don't want to talk to you, you can also use them as an opportune moment to wrap things up.
Don't be overly solicitous
Sometimes shyer people won't speak up when they want something from you. The other person 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 rent? 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 slightly 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, even if it would be the normal thing to do with a more outgoing person.
Don't take it personally if they want to escape after spending a few hours with you
A well-worn cliche is that less naturally social people get 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 that person wants 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 experience 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 just 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 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 to be around 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, and/or only talking about what they want to discuss. But what happens when shy people seem annoyed at them? "Oh, well you're more introverted. It's no wonder you can't handle them." Yes, maybe some people do need a slightly thicker skin when it comes to tolerating outgoing people, but at the same time, don't write-off their legitimate opinions with, "Well you're an introvert, so..." This is both irritating and makes them feel misunderstood.