It's the poking and prodding you talk about that usually keeps me in my shell. When I don't know someone and they have a big personality (and/or they poke/prod), it just kind of freezes me in my tracks. I detach and observe. While I'm observing, I don't want the attention on me - because that means I can't observe because I have to participate. Let me observe, allow there to be moments of no talking, and it will come.
Reasons:
1. I want to know where you're coming from and that takes time (usually multiple times hanging out with you). Are you just an egotistical person that's going to make me feel uncomfortable every time we get together, or am I going to be able to really relax and be myself around you (and you'll be cool with my introversion and who I am)? That's a big one. I hate hearing stuff like, "he's so quiet", "he's this", "he's that". I wanna know that the person is cool with me being me.
2. I know it's going to take a lot of mental energy to engage you in back-and-forthness all night. I want to pace myself and pick my spots to engage.
The quickest way I will open up in these situations is if the person has some N. Start talking about intellectual stuff or going in-depth on a given social topic or something along those lines and, as they say, "it's on like Donkey Kong". But, that's probably different with type. I know an ISTP, for insance, who only opens up once you show that you are funny. I know an ISFJ who only opens up once she knows she has something in common with you and can trust you.
But, if it's just stuff like, "why are you so quiet?" "Why are you shy?" "Say something or I'm just going to stare at you and make you feel uncomfortable". Just isn't going to work. That just shows that you're willing to make the introvert uncomfortable, and that makes them not want to trust you in a sense. Show that you can be funny and all that, but not at their expense and not if they seem to be somewhat uncomfortable. Take it easy on them, and they'll open up in time (maybe not the first time you hang out with them either). Let it come out on their terms, not yours.
Word. I need to know that someone isn't trying to change me. I need to know they like me for me. With men, I feel so much more comfortable when I know they're not interested in me romantically or sexually. If they don't make that clear, I'm always seeing their motives as suspect.
As you said, start talking about something--I hesitate to say it--"deep." I don't know what else to call it, though. But that's the ticket for me. People who actually think about things and reflect on things, people who turn over things in their minds and tinker with questions, people who see things wrong with the world and can passionately rant about them, those are the people I hang out with. We don't have to have deep conversation every time we hang out. In fact, my best friends and I frequently just get together to play Boggle or some other game, and nothing of substance comes up.
Also, I enjoy people who share my sense of humor or just like to do the same things I do. If we can do little more than take a trip to the grocery store for snacks, or Wal-mart for essentials, and then come back and watch The Office or South Park or anything funny like that for a few hours, and call it a good night, we can be friends. I'm not into bars and clubs, but then again, I've never been to either.
The whole point of me trying to get people to open up is to try and get to know them better. Often times with introverts, it's hard to get to know who the people are because sometimes they hide so much of themselves from the public (that's why I poke and prod), and every time I don't manage to get to know someone I interact with a lot, I feel like its a missed opportunity and it hurts me because I always think - if only I tried harder. Why I feel this way, I don't know? Maybe its because I feel like I've missed some of the beauty in this world because of my inattention or inadequacy.
I do all those things, poke and prod, make jokes, have conversations, ask questions, in a very gentle manner....with most people...and still it often doesn't work.
Sometimes I also wish to help individuals that I care about who are hurting, usually INFPs, but I find that I am often unable to access them.
I just want to be able to get some shy people to open up. Maybe because I want to establish closer relationships to them. Maybe because I just want to get to know who they are. Frankly, I feel its a skill I need to be able to have.
I relate to this. Introverts are difficult to open up, maybe especially for other introverts. An extrovert, especially a confident and assertive one, is persistent, and that's their biggest ally. If they don't lose patience completely or give up on the introvert, as long as the two people are compatible as friends, it will probably work out. They'll probably be friends. But introverts have a harder time being outgoing and pursuing other people, especially introverts that aren't confident in themselves.
My suggestion... might be to just have the goal of somewhat regularly hanging out with them. For an introvert, especially a studious or workaholic introvert, this may be once every two weeks--but for people like me, that's "regularly." Just have fun hanging out with them. Be genially persistent. Invite them over once a week. If you know they're shy, entice them with the knowledge that it'll be just you, them, and maybe one other person they've already met and seem to feel comfortable around. If there is no such third person, just let it be you and them.
There was an extroverted (seemingly, though he denies it) guy who, one day while we were partnered up in class, asked me for my AIM screen name. I think he asked for it because of something I said, something that made him interested in me. I might have said something about a theory I had about human behavior, but whatever it was, it made him tilt his chin up and regard me with curiosity. I could tell he was interested in me primarily
intellectually, in that moment. It's why I asked him for his screen name (although it's possible I did it out of politeness).
So he messaged me one night on AIM and invited me over. It would have been more awkward, but he made it clear he wasn't interested in me romantically or sexually. And he's been pretty consistently asking if I want to hang out ever since then, which was several months ago. We've found some activities that we like. He doesn't have to have a ton of people over all the time. Usually it's just him, me, and maybe his roommate, and he knows I prefer that.
It takes time. It won't be instant. It might take them a while to warm up to you. They probably won't immediately start inviting you over, and they probably won't immediately start texting or calling you to hang out. But if you can find things to do and things to talk about that you both like... INTPness made the insightful comment that it varies widely from introvert to introvert.
If it's an IN, you can bet they'll probably enjoy engaging you in rigorous intellectual conversation. But find their nerve, if you can. And find mutually enjoyable activities. And be
gently persistent. Don't put in too much effort, because that can get annoying and make you seem needy, but make it clear you're interested in them as a friend and like hanging out with them, enough that you'll go a bit out of your way to invite them over and make them comfortable.
I'm an INFP, if that makes any difference.