I know carrying a conversation is really a matter of both parties being interested in that, but I feel I'm pretty good at getting a conversation going if I get any response at all. I only need a little to get things going so I don't have a problem there. I just don't get any responses at all; so on my end (similarly to the guy above) I don't feel that great (like Dan does) about online dating. On top of that problem I don't like the idea in general. It feels really gross- like you're thumbing through a magazine and being like "I like that one *skeezy Jeff breathing*." I know that's how dating services have always been, but it's weird thing I have never particularly enjoyed engaging with.
I just wanted to hop on this little topic, since it seems like even Dan with his do-anything attitude still has trouble with this.
I'll let you guys know what works for me: say something dumb. Seriously, that's it. Icebreakers are always dumb. I had a sales job once, lasted around five months, didn't end up being for me, but it taught me the value of not being self-conscious. I was in South Atlanta, the only white man to be seen that entire day. I had to walk into every store I saw. I saw crazy Haitians. I saw lots of shit. But I had to start conversations with all these people.
By "dumb" I don't mean stupid, I just mean something obvious to get people to feel comfortable. Most people are a lot like Mr. cornbredx here and will open up given half the chance - you just need to give them that chance. Comment on their weird shirt. Ask them a question. Comment on the weather. Whatever. It's not rocket science. The point is just to get a reaction. Usually, if there's any sort of chemistry or something in common, that will be brought out pretty quickly. I had to try and sell a guy in a barber shop cable once, and he was really defensive - it was an all-black part of town in the Deep South, and here I am, a tall white kid trying to get this hard-working dude to buy something he probably doesn't need. But the second I noticed the music that was in his store, I commented on it, and he went off on this long (fascinating) tale about how he met Michael Jackson. Got a sale out of it, too.
Now I'm totally that guy the Dans derided on their podcast who will absolutely talk to complete strangers walking around. Do it all the time. It's a lot of fun, and quite rewarding. It's way easier without any ulterior motive. I dislike the online dating thing because it's impossible to get solid reads on any response you get via a text - speaking to someone in person is so much easier, because they're usually at least polite and you can always tell when they're uncomfortable.
Last tip: try to not be interrogative. Don't ask a lot of questions that can be answered with a yes or no. So for instance, if I were to talk to a complete stranger in a bookstore, I might ask them: "Hey, sorry to bother you, but I'm looking for a book for my mother for Valentine's Day and I'm not really familiar with *insert genre*. Do you know anything about it?" They can totally blow you off, or they'll start talking. It's all about that nudge.
Hope this helps.