Transitioning a conversation

[LordSappington]

So, as you probably know, I'm bored out of my mind tonight, so I'm starting another thread based an interesting observation people made in my first post. It became very clear to me that, although I have learned to initiate a conversation, my conversations pretty much fizzle and die out after the first few introductions and discussions (name, where you were born, where you work) because, since I initiated, the other person expects me to transition it. I think I start conversations but really have no idea how to transition from smalltalk to something more substantive (or fun) that could end in with me bonding with the other person. So, what are your top strategies to end small talk and discuss something better? Do some work in certain contexts (bar, gym, sports, party) and not in others (networking for work, standing at the bus stop)?

Yeah, I know I'm overthinking, but none of this really comes naturally to me at all for some reason.

[AlexG]

- Become really interested in a person. You can't really fake this, you have to be honestly interested.

- To carry a conversation further, look for certain words when the other person is saying. For example taking your first sentence "So, as you probably know, I'm bored out of my mind tonight, so I'm starting another thread based an interesting observation people made in my first post."

I can carry on a conversation with you on variety of topics that you brought up. I could ask or comment on the following based on your first sentence.

- your boredom tonight
- another thread you made
- what was the interesting observation others made

That is just from one sentence. Pay attention to what others are saying, extract what they are talking about and carry the conversation.

[LordSappington]

AlexG: Those are all good suggestions, but I was asking something a little bit different. It seems that most of that stuff is still a bit fluffy. Let me give an example.

I ended up at a bar for a happy hour. There, I met a social work student. So I asked her what her goals were (this is easy with social workers because they have so many options: therapy, home evaluations, research, etc). She wanted to be the director of a local youth group. So I asked her what ages the youth group was and what kind of activities they do. She told me about some trips abroad that she has led and some other programs. I said I could never handle those kids and suggested that she must have some interesting stories dealing with 12 year olds, her being a 25 year old woman. She told me some. But it seemed like we never really transitioned from "what do you" to any conversation that really engaged her. It was clear to me that she really loved her work with the children, but I felt that I never really asked the right question to get her to open up about it and the rest of her life.

Eventually, the conversation died and she went to talk to some cocky, smart-aleck law student and ended up talking to him for the rest of the night. I got cut out of that conversation and wandered over to a different circle and chatted with them for a bit before heading home. I've had a lot of there conversations, when I desperately try to get them to talk about something they find interesting, but they just don't want to come along for the ride. So, what could I say to help them along?