I need to work on my conversation skills, particularly with strangers and meeting people for the first time. Any tips on keeping conversations going?
A good tip is to remember to ask questions. I have found that when conversations with new people are not going well for me, it’s because the other guy is asking me stuff, and I supply the answer and then stop talking. So I got in the habit of remembering to ask a question after answering one.
#1 rule I learned (for hitting on chix, but worx on dudes too) - get them to do most of the talking, then repeat back keywords of what they said, & craft as a question.
ex. Chick: ‘bla bla bla and then I decided to take pottery class.’
Me: ‘Pottery class? That sounds so interesting. Hey, how do they turn the soft clay into hard pots, what’s the process?’
Chick: [after 5 minutes of kilns, firing, picaware, etc.] ‘…so then after shaping the handle it’s just a matter of letting it cool off’.
Me: ‘Cool off - sounds demanding & like you could get hurt. Did you ever have a pottery-related accident?’
Chick: 'well, there was 1 time I was talking on my cellphone while taking it out of the kiln… [5 more minutes of accident description] '…so I learned to be careful when around kilns & other hot objects.
Me: ‘Other hot objects? Why, what other dangerous hobbies you have?’
and so on.
I’m told I’m ‘a really good conversationalist’ 
- Have really big boobs and the rest kinda takes care of itself.
If you don’t have big boobs or you are a dude:
-
Having a drink can help you overcome small talk stage fright and loosen you up a bit but don’t get drunk.
-
Ply the other person with drinks but don’t get them too drunk that consent is no longer possible.
-
Find something you have in common, if you both have kids, talk about having kids but don’t monopolize the conversation talking about your kids, noone you just met really cares about your kids, they are just waiting for their turn to talk about THEIR kids.
-
Find a common interest if you can, that sort of conversation can last all night.
-
Find something that really annoys both of you and help them bitch about it. That sort of conversation can last a lifetime.
-
Avoid conversations about politics or religion unless you are at a political rally or at church. If it heads in that direction then quickly divert the conversation to some event so far in the distant past that noone can possibly take offense at it.
But mostly number 1.
I have big boobs and I struggle with small talk. Mostly because I need to do a better job of remembering friedo’s tip. Ask more questions than you answer, even if it’s only turning around the question you just answered.
Them: “Did you have a good weekend?”
Me: “Oh, yes, we went camping.”
dead silence.
Works much better if you try:
Them: “Did you have a good weekend?”
Me: “Oh, yes, we went camping. How 'bout you?”
Them: “Oh, it was awesome! My mother in law brought her pet iguana over to visit and my dog thought it was a dragon! Blah blah blah blah blah…”
I’ve found that 90% of the time, when people ask you a question, it’s because they want *you *to ask *them *that question.
Remember someone’s name. People like that, especially if they have an unusual name.
/unusual names are easier to remember.
Having big boobs doesn’t guarantee that you’ll get GOOD conversations, though. It does guarantee that you’ll get a lot of clueless guys ask for sex, or for “dates” (by which they mean that they want to have sex immediately after a Big Mac). Some guys think that if a woman has big boobs, that she’s willing to sleep with someone at the drop of a hat. Or bra. It ain’t so. Nor are big boobed women interested in ONLY sex. Some of us have brains as well as boobs.
I used to be 38 (DD) 27 37 when I was in my teens and twenties. And yeah, I had a lot of guys chat me up with the clear intention of getting me into bed, and no other reason. My problem with these guys was usually ending the conversation, and finding someone else to talk to. Someone who would look me in the eyes when I spoke, and not address my tits.
The suggestion of asking questions is also excellent when someone asks you something you don’t wish to discuss.
“How much money do you make?”
“Why are you asking?”
“Just wondering.”
“Do you ask everyone you meet?”
“Yes.”
“Why?”
etc. etc. etc. Just pretend you are on Jeopardy and keep asking questions, never give an answer. This can go on for hours until the nosy person gives up.
But yes, asking (non-prying) questions is always a good idea to keep a conversation going. Most people, even shy people, are more likely to answer a question about something they know about than initiate a conversation. This works even with little kids as well as great-grandmothers.
Wow. What great tips you’re getting!
My suggestion is actually a book: “How to Win Friends and Influence People,” by Dale Carnegie. Reading it changed my life, no joke. And I know the title is cheesy and sounds vaguely manipulative. But the book could just as easily be titled “How to Be a Kind, Considerate Person.” The friends and influence are a natural outflow of your good characte and, yes, wonderful conversation skills.
There’s a reason this book is a classic. It’s excellent. 
What made you decide you need to work on your conversation skills? See, that’s how you do that.
I don’t want to sound like this is a science, but I think I’ve learned it helps to identify the general idea why you’re talking to this person at this moment. A lot of people say they hate small talk because it’s pointless, but anytime you feel like you ought to be talking, there’s a point, even if the point is that it’s awkward to be in an elevator with one other person who you must obviously work with or near and not say anything. In that situation, all you have to do is say anything that’s not more awkward than the silence, and you’re a winner. They don’t give a shit beyond getting past the next 45 seconds, and neither do you. So, uh, what’s a thing… getting trapped in an elevator! No, fuck, not that… “Ah, Monday morning.” “Yep.” Zing! Remember, small talk is always scored on the small talk scale, not on the is this person a leading intellect scale. If you’ve established any kind of rapport and not offended anybody, everybody else appreciates it, or at least acts like they do, which is good enough.
But like right now I’m talking to you, and the point of talking is that you need to work on this thing. It’s not about me or just talking for the hell of it; you have a problem. So here I am. I’m interested in that; tell me why that’s true. The conversation is continuing, and the less I’ve said up to now, the better a job I’m doing (so I’m not doing a very good job).
Just find someone your comfortable with.
some people are easier to talk to.