How can I get good at having conversations?

I think what you’re talking about is “small talk” which is inherently different from a conversation. Conversations play out on their own steam because they’re about SOMEthing. Small talk doesn’t have to be linear at all, you just have to pick up on one item from each exchange and redirect it. Example.
“This is good coffee.”
“Where’d you get it?”
“Russo’s. Over on 3rd street.”
“There used to be a great dry cleaner over there.”
“Yeah, I know. I can’t find one in my neighborhood.”
“Where’s that?”
“Willow Hill.”
“I used to know a guy that lived over there. You know Joe Smith?”
“Nope.”
“Oh. Well, have a good one.”

and right there, you have a brief, friendly conversation about absolutely nothing. I know it seems silly, but the basic idea is sound.

From Monday to Wednesday, ask what they did over their weekend. From Thursday to Friday, ask if they have any fun weekend plans… this is my standard “make small talk” guide when I can’t think of anything to say! Based on their weekend plans, you can ask other questions about them (if they say they’re seeing a new movie, ask them what kinds of movies they like, if they’ve seen anything good lately, etc…if they say they’re just hanging out with their family, ask if they have kids. If they have kids, you’re golden, because people love talking about their kids, etc).

Or, when in doubt, ask them, “hey—have you heard of this great new website called Fluther?!” ;)

How old are you, and what kind of job? Some good advice from GD and occ as usual. I would eliminate “suck” from your conversation if you are over 16. Can you talk shop? That is alwasy safe. Do you find a difference when chatting w. men or women? And, how about them Mets? (Bad example, sorry.)

Sometimes people avoid chatting because they’re afraid of saying the wrong thing, or they’re trying to come up with perfect thing to say. As long as you don’t overshare and put deeply personal things out there in what should be a small-talk conversation, whatever topic you decide to cover should be fine. Also, just asking a lot of questions (but not too personal!) about the other person usually helps to keep the conversation flowing—people love to talk about themselves.

It’s difficult to say the wrong thing if you’re actually paying attention to the other person, reading some clues, letting them teach you.
Be kind (they’re shy too, you know) and with that in mind, try to learn something. Anything. Keep a little notebook of what you learned from otherwise pointless conversations. See what’s in the notebook on November 9. Then report back.

You may not realize it, but you probably have a big thing going for yourself by NOT being a big “talker”. Many, many people like to talk, yak,yak,yak and if you’re a “listener”, they love it. You just have to truly listen, smile, look at them & oftentimes, replies will just pop into your head.

i’m horrible at conversations, i get all nervous, and sweaty, and twitchy…i’ve found that the more you do it, it gets a teeny tiny bit easier. EASIER, by no means is it easy, for some…