Twenty three years on the planet and I still haven’t figured this one out. So I’m turning to you guys for some help. What I would like is to have most of my social encounters not dive into awkward silence after only a few minutes.
What can I do to keep up a conversation?
When you find out, let me know. I’m totally at a loss at parties, and don’t know how to jump into or maintain a conversation with strangers. Friends and clients, no problem - I can be interesting and witty when the relationship already exists, and do OK if there is some external shared experience that I can use. But I never learned how to chat with random strangers.
A few thoughts. People like to tell you about themselves so let them talk. Ask questions about them but don’t pry. Just keep nudging the conversation along. Don’t stare or anything but treat people like they’re important and what they have to say is important to you.
To get the conversation going in the first place you need to talk about the weather, something they’re wearing, let them ask about you, you’ll have to feel that one out. Not every one is looking for a conversation so don’t be pushy, just go with the flow.
I find drinking to excess helps, sometimes.
But in all seriousness, it’s not hard. Just think of something about the person that your interested in and either make a comment or ask a question.
Also, I feel it’s all in your attitude. If you just have the mindset to love and be loved in return (or something to that effect), most everything will come naturally.
Think of a conversation like a Wikipedia article. If you’ve bored of the topic at hand, “click some links” of other keywords in the conversation to find out more. You can spend the entire conversation learning - and you don’t need to know a thing.
Well, you keep doing whatever you were doing the first few minutes before it dived into awkward silence, really. It sounds like a really dumb answer, but it’s the truth. One of you just has to kind of pick something and run with it those first few minutes, right? Well, to keep things going, you keep picking things and running with them. It’s usually easiest if the thing you pick to run with is somehow related to either what you were talking about previously or the task/situation at hand.
For instance, if you’re at a party and introduced to someone that you don’t know how they know the host, ask them. They’ll tell you, and then ask how you know him. Tell them, then you can either ask about something related to how they know him, or tell stories about stuff you’ve done with him. Say this person went to college with the host–ask about them having classes together, or what this person’s major was. Then keep following the same procedure from there.
Judging by what works on the SDMB, I would suggest saying something provocative about religion, gay marriage, gun control, or the economy. Possibly talk about kittens.
Note that this may not have quite the result you were hoping for 
I always like to recommend the book How to Win Friends and Influence People by Dale Carnegie. Ugh, what a horrible title. It sounds so manipulative. But the advice in it is really sound, and there is a section on just what you are asking about.
But, yeah, as someone pointed out…people like to talk about themselves. Just keep asking specific questions and sound really interested. Try to not to interrupt with your own thoughts. Wait until a natural pause in the conversation and say what’s on your mind. Nothing on your mind? Just keep asking questions.
The next question you’ll ask is: “How do I get OUT of these conversations?” 
Have a couple of questions on reserve for those times when you seem to run out of conversational steam. Be observant, keep an eye out for clues about the other person’s interests and tastes.
These reserve questions need to be tailored to your social group or your perceptions of the person you’re talking to, but don’t have to be too specific. If it’s at a social event like a party, ask what they’re drinking (if it’s not obviously emblazoned on the side of the bottle) or comment that you haven’t tried Newcastle if that is in fact what they’re drinking. Then you can kill a few minutes discussing the finer points of your favorite beer/whiskey/whatever.
Sports teams, books you’ve read recently, blockbuster movies, etc can all be kept as reserve questions depending on who you’re talking to. These help prevent or delay those awkward conversational spells.
Always talk about yourself. Fuck other people.
Ok seriously now. As has been said, get them talking about themselves and/or what they like ("So you’ve written 6 Battlestar Galactica stories?).
Also, self deprecating humor is always appreciated. Nothing super (It’s THIS SMALL!) but just small (heh) things that are topical and fun.
That some solid advice right there, and while you’re at it, take HongKongFoey’s advice and be sure to pry into their life, nudging them and staring is also helpful…Wait, maybe that’s backwards.
If they’ve mentioned things like their work or hobbies and you hit a lull in the conversation, say, “So tell me more about your work/hobby.” Maybe you’re really not interested, but if they keep talking it may spark other questions or your own stories and go from there. I once had a 3 hour conversation that started with talking about how the motor home we were driving in was making us motion sick. I think the topic changed every 20 minutes or so.
Don’t sweat it about being 23. Having lots to talk about just comes as the years go by.
That’s a great suggestion. I’d second it.
During one of my classes in college, I was forced to read it. After reluctantly picking it up and reading the first chapter, I pretty much never put it down. Got the whole thing done in about three sittings.
Yes, but it also has the single worst piece of advice ever offered: keep repeating the other person’s name, that they love hearing their own name. It drive me up the wall! At trade shows I’ll hide my name badge from random booth critters can’t find it and proceed to Dale me:
Hi Gaffa! How are we doing today, Gaffa? Like what you see, Gaffa?
The purpose of small talk is to keep finding out things about a person until you find some common ground with which you can connect.
Make it your mission to find out as much about other people as you can. Make a mental set of questions you can ask and use one whenever one of those awkward pauses rears its ugly head. It will feel weird at first but you’ll get used to it.
The simple fact is, most people absolutely love talking about themselves and are flattered when someone else shows an interest in them. You still want to play it a bit cool, you’re not interviewing a murder suspect, so try not to come off too strong.
The best questions are ones where you can ask them something, get their answer, then offer your own opinion as well, thus giving them the opportunity to learn about you as well. You generally do this by starting with a general question to get some yes/no information, then probe for detail, then provide your own detail.
When you’re providing your own detail, be honest, don’t make yourself out to be the most amazing person on the planet, but also don’t make yourself out to be the most boring person on the planet. People don’t like listening to others talking about how awesome they are, but equally, they don’t like listening to others talking about how crap they are.
A bit of self-deprecation can put someone at ease (‘You play guitar? I tried to learn guitar once but I really sucked at it. I think I’ll stick to air guitar in the safety of my bedroom. How long have you been playing?’) but no one wants to hear Sally Sadsack (‘You play guitar? I tried to learn guitar once but I really sucked at it. in fact, I’ve always sucked at any instrument I try to learn. I’m just not at all musical, it makes me really sad. I wish I was talented at something, anything.’)
Here are some starters for ten:
School/University
What year are you in? What subjects are you studying? Any idea what you want to do as a job? Do you get much free time or are you studying all the time? What’s the school/campus like? Do all your friends go there as well?
Work
What do you do? What does that involve? Do you enjoy it? Is that something you’ve always wanted to do or did you just fall into it? Are you planning on sticking with that for a while or are you looking for something else?
Home
Are you local? Did you grow up around here? Has it changed much from when you were young? When did you move here? Why did you move here? What’s it liked compared to where you grew up? Do you think you’ll stay here? Would you like to move back to your hometown one day? Is there anywhere else you want to visit?
Leisure
Are you into sports? Watching or playing? What do you watch/play? Do you do that quite seriously or is it just for fun? How long have you done that? Have you got any holiday plans this year? Where are you going? What makes you want to go there? What are you going to do and see there? Have you been there before? Do you know anyone that’s been there?
Music
Have you heard this band before? Do you like this kind of music? What’s your favourite band?Ever wanted to play an instrument yourself? Can you sing? Are you musical at all?
Friends and Family
Do you have any kids? Do you have any brothers or sisters? How old are they? Do they go to a local school/university? How do you know Joe Bloggs? Do you know anyone else here?
Compliments (I’m a girl so I’d say these sorts of things)
I love your scarf, where did you get it? Do they do them in different colours? I’ve not been there before, where is it? Do they have other nice things? What are their prices like?
Lots of conversations end up fizzling, so don’t think it’s just you. If you feel like talking to someone, just talk to them. You aren’t obligated to speak to people who don’t interest you.
The best advice anyone can give you is to loosen up. Don’t be afraid. Don’t be timid. If the conversation dies, or you start to realize you aren’t interested, treat it like a car that broke down on the road. Just get it out of the way without causing trouble, and don’t try to push the damn thing all the way home.
There’s lots of good advice here. One thing that helped me was to hang around people who are good at conversations and and notice the kinds of things they talked about, and how they handled awkward pauses, or responses. Some people are such adept communicators, it’s really fun to listen to them. I’m still not great at small talk but I could do it to save my life now. I think “what would Nicky say here?” and go from there.
I second this. It sounds cheesy, but it’s really a wonderful book.
Ask the other person about themself. What do you do for a living, where are you from, etc. Get them talking about themself and listen to the answers. Ask followup questions based on them, especially if you can steer the conversation into something you know about.
Example:
Clothahump: Hi, I’m Clothahump.
John Doe: I’m JD
C: Nice to meet you, JD. You from here in Houston?
JD: Just moved here from Austin.
C: Really? What part of Austin did you live in?
JD: University area.
C: Cool! When I lived there, Dirty’s was the place to go on the Drag. Is it still open?
Now I have established rapport with them: we have both lived in Austin. The conversation will take off from there.
Print this and keep it in your pocket. When a conversation lags, unfold it and read it aloud.