The Art of Conversation

I used to suck at conversations with a similar background as you, but I am quite good at it now when I need to be. My rule of thumb is to ask lots of questions. Most people love talking about themselves, and if you seem interested in them it will leave a great impression. Just think of the question words and make questions, doesnt really matter if you are genuinely interested or not. Of course, it helps if you listen to people so you can use their responses to prompt more questions.

If you cant think of more questions or run out of them, another trick is to use physical things to keep conversation going. Stuff like, "that is a nice ring, what's the story behind it?" or "I really like that tie, where did you get it? Ive been trying to expand my wardrobe a bit." etc.

Similarly, when answering questions I'd suggest not stopping at simply giving an answer. By that I mean, don't just answer, but answer and then explain. For example, if someone at a party asks "What do you do?" Don't just say "I'm a software developer." Instead, say "I'm a software developer, but it's not something I ever thought I'd end up doing. I originally got into programming as a hobby and decided to go back to school for it a few years ago." This is a lot easier if you don't have some boring ass vanilla life, though.

*Edit* I should add that I am an extreme introvert, and I find it quite literally physically exhausting having prolonged conversations with strangers or having to mingle for extended periods of time at work events or parties. However, with practice I've gotten to the point where I have recently been complimented on my conversational abilities, and people were shocked when I told them I hated talking and that I was an introvert.

Stay up on local news, events, & happenings, so that you have something to fall back on once you're out of conversation ideas.

"So...have you been to any (insert local sports team here) games lately?"

"Did you make it down to (recent local festival/celebration/event) last weekend?"

or just the always lame, but successful comment on the weather or their family(if you know a little about it already). (Boy, sure has been (hot/cold/rainy/dry) lately, huh? How are your kids doing? What grade are they in now?)

You pretty much have to start out with a broad, general subject that lends itself to smalltalk, and once you get a person going they will hopefully put a few more detailed comments about their life out there that you can expand on.

If you ask them if they saw last nights game, even if they say no, they'll usually give a reason as to why. Working, out doing something else, etc, that can invariably lead to follow up questions ("Oh, where do you work?, or "I've heard thats a really good restaurant, did you like it?")

It's just a little more natural flowing than to grill them 20-questions style about their life. Like, you didn't just randomly ask them where they work, or what they do, they mentioned first that they were working late, so following up on that subject feels more natural, and conversational.

Start smoking then you can put the cigarette in your mouth instead of standing there being akward during the pauses.

Just ask them if they're Red Sox fans. If they say yes you don't want to talk to them anyways.

Hoss_sl said:

I hate hearing my own name. I run away from people who do that.

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Okay, Hoss.

If things are getting awkward just take all your clothes off.

Hoss_sl said:

I'm tricksy. I didn't use my real name as a forum handle.

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Learn about your local sports team, more often than not that can get the convo started or can move things along well with most gentleman.

Everything that McCheese said is what works best for me, I'd also consider myself a pretty strong introvert.

Don't talk to strippers either.

heyholetsgo_sl said:

I suck at having conversation. When I try to talk with people there's always long awkward pauses. Its clunky there's little to no flow, etc. I usually just try to end it as fast as I can because I suck so bad at it.

A bit of a history to see where I'm coming from. Grew up playing video games, didn't play sports or any kind of group/social activities. Shy, quiet, didn't really want to talk to people that much.

It used to not bother me at all, but as I get older(29) with a wife and kid, I'm seeing the value in it and the potential connections that can be made through it(i.e. career advancement, getting in with different crowds of people, etc.)

What am I not doing? What are your go to conversation fillers? Is there any resources you guys could recommend to help?

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Get a part time job doing retail for a while. Get used to helping customers, talking to anyone. Preferably in something you know about so that you have knowledge to give. Practicing explaining basic stuff to different types of people helps you learn communication skills without bothering about content as the content is automatic.

Yep, retail is what helped me a lot. I'm an introvert, always have been, but I'm absolutely comfortable talking to anyone about anything thanks to retail work in the past. You're basically forced by your job to greet & strike up a conversation with strangers all day long, every day. Becomes super easy.

Hoss_sl said:

Why would you say that? You couldn't be more wronger bro. I'm quite introverted too and was pretty much afraid of women till my late 20's. Stripper therapy cured me of that.

BTW, isn't it safe to assume we're all introverts on this board? I think someone only needs to identify themselves if they're not.

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Well, first of all he's married with a kid, don't think his wife wants him to go hang out at jiggles to work on his social skills.

It also sets a bad precedent since they are only interested in the money so it's not a traditional conversation. You can rattle on about how wicked your model train set up is and they will feign interest as long as the money is flowing.