I engage in conversation when I'm looking for feedback on ideas I've come up with or advice. Outside of that, it's scarce. Some of the reason is certainly that I'm simply not interested in the sorts of topics most people like to talk about. But ability is a factor too. I have no idea how to talk about everyday things without sounding trite. And for people I don't know particularly well, there isn't really anything else to talk about initially anyway.

I can be funny but in a "plodding thinker" sort of way - that is, I may be able to develop something over time but rarely at the spur of the moment. It makes me think that perhaps I should try develop a "script" to some degree, trying to open things up and then go on freely from there. Even then, it still needs to be in the form of the "everyday greeting", which as I said I'm not good at.

You need to involve yourself in social situations more so you become comfortable interacting with complete strangers. It is not an easy thing to do, but the more you practice the better you get.

Mastering small-talk takes time....and some people are naturally more introverted than others, so it may be more of a challenge.

The thing is, it's sort of a catch 22 - that I need to learn conversations in order to start conversations. Fine for the long run, but what should I do in those initial conversations?

learn how to socialize high and you will be the best talker around...

i generally try to find some area of common interest, there must be something ya know?,
and then go from there.

loosen up a little bit, if you're going in to it w/ some rigid preconceptions chances are
you're going to give off that vibe as well.

i generally hate small talk, meeting new people as well. it's funny watching my younger
daughter interact w/ people at say the playground. she can be quite shy sometimes,
but most days she's just all over the place trying to meet new people regardless of age.
something i've noticed that she does is to usually pay the person some small compliment. like 'i really like your shoes', something, anything really. it amazes me sometimes the things she will pick up and comment on and it kind of disarms the
person i guess. starts things off in a positive way. i don't know something to think about.

good tip I heard is that you should tend more to make statements than questions.. almost every chitchat question can be turned into statement.. some observation or something like that.. you know what I mean?

Um I vote for exactly the opposite. Ask people questions about themselves, their lives, something they've shown an interest in. Choose something you yourself are at least remotely interested in so that you can actually listen. If you find something interesting, mention the fact, or ask more about it; if you can relate, share a story of your own; is there something silly (in a good way) or funny about their experience? Mention that.

Don't talk about yourself. Find something interesting about the other person, or something they are interested in, and ask them questions about it. A person's favorite conversation topic is always themselves. Let them talk about themselves, and they will do all the work.

"Do you enjoy your work/school/degree/family?" "I've always wanted to know more about X" "I would think this aspect of X would be difficult/fun."

While they talk, think about what follow up questions you can ask them (as opposed to thinking up a reaction and story about your own life, which most people try to do).

yea but you didn't got the point.

i.e. instead

you:"how was at your work today?"
he/she: "ok."

you can say

you:"you look so tired, must have been a hard day at work"
he/she:"yea sucked **** to boss bla bla bla"

it's about rephrasing, not having no interest in them.. if you make statements, conversation flows more naturally etc.

Your initial attempts will probably make everyone involved uncomfortable for the most part but it's necessary so you can get the experience and figure out how to get better at it.

try talking to her

really, though, just strike up conversations with every you can. try to keep in mind that you will most likely never see them again so it's really not a big deal if you embarrass yourself.

People like talking about themselves, generally let them talk about themselves then pick something from whatever they're talking about and make a statement about it and they'll respond etc.

An interesting fact, those that are considered the best conversationalists rarely speak themselves. They engage others to speak.

Just a random thought...

I feel like there are insane, massive gaps in how hard conversation with randoms is based on location (within the US). In Minnesota, I constantly feel like I am carrying conversations, whereas in Kansas, I tend to feel as though I am just along for the ride.

QFT

Being a good listener is a better skill than being and good talker

Much of my problem is doing this without sounding like a tool, especially with people who are somewhat reserved. It surely doesn't help that I thoroughly do not care about what the vast majority of people have to say for themselves, creating two problems: my insincerity presumably shows and conversations are "more expensive" for me than for most people.

Get friends you do find interesting? You're not twelve. Either choose cooler people to hang out with or make yourself better so that cooler people want to hang out with you. I can't stand talking to most people but even I hop on the subway just to drink a couple beers and yuk it up with my guy friends.

Have you tried alcohol?

I used to feel the same way, that most people were too boring. But if you actually talk to them, almost all people do something or have been somewhere that you've wanted to know more about (your age could be a factor in this, young people are very boring, especially college kids). If you're having trouble finding it, just think of the conversation as a game you are trying to get better at. See how long you can go without the target looking around for someone else to talk to.

If the issue is with people you don't know - I think it's the same as talking to women - talk to them like you know them. It takes the tension away. And if you are talking about friends, just acknowledge their trite topic like "yeah, the traffic is bad" - pause - "did you see that show/that play in the Eagles game/that movie/whatever. Just switch the direction and tone of everything.

I can quite often engage in interesting banter with people. The problem is, it lacks substance. I liken it to performing stand-up comedy: I make them laugh and smile for a while and think I'm doing well. But as soon as I'm out of material, I'm back to square one, still not really knowing anything else about the other person (potentially warming them up to be asked, yes, but I still have to figure out how to do that).

tell a joke thats not funny

or ...we had a teenager show up his first day of work and tell us hours later in a serious tone that "i had 3 hot girls ready to get on me last night"
we obv all laugh
It definitely took any new guy awkwardness out.

My peers often tell me I'm the best conversationalist they've ever talked to. What I do is try to find out what they are interested in, and get them talking about, and I often rephrase what they say and just mirror them, I also break in for the occasional ancedote or short story relating to the topic of interest. Also I am pretty witty and funny I guess I was born that way.

Don't go back on a topic when you've left it and it's worn dry. It's ok to have moments of pause and silence. You don't have to talk about inane stuff neither of you are interested in just to keep a running dialogue.

Oh I think it's worth mentioning that meaningless entertaining banter conversation should be interspersed with more deep serious conversation. If you only talk about air they'll come away feeling like a meaningful connection wasn't made. But if you can't lighten up the conversation will seem too intense and serious. You have to feel when a serious or light topic has ran it's course on a person and then look to switch.

I haven't read any posts. To be a good conversationalist all you have to be is a good listener. People love talking about themselves. All you have to do is ask them good questions about themselves.

Good listening is bs. Spend lots of time with people and practice.

That's not enough. If all you do is ask someone questions about themselves you wind up with a one sided interview where nothing between you is shared, no rapport is built, and they learn nothing about you.