Medium Talk

I'm great at small talk. I love meeting people, finding out where they're from, what they do, who they know, etc. I am constantly meeting new people- networking groups I'm in, conferences, new families at church, friends of friends, camp, etc. so it's not uncomfortable for me to have initial conversations with people.

I also really enjoy deep and meaningful conversations with people. I love to have people teach me about their religious and political perspectives. I love hearing about big moments in peoples' lives that have shaped them and changed them. I love conversations where we get to know things about each other and conversation leads itself to sharing the important things to us.

What I'm not good at is the stuff in between, which I will call "medium talk." So, what I mean by medium talk is the next step up from small talk up to a few notches below we're good enough friends to figure out how to talk about things that matter. I don't really know how to ask questions in that zone in a way that doesn't feel forced or awkward for them or me. For example:

Me: Hey! How are you?
New friend: Good, how are you?
Me: Good! What's new?
New friend: oh not much.
Me: Cool!

I could maybe try "what are you doing this weekend?" after this, but if further conversation hasn't ensued after weekend talk, any get to know you kind of question I can think of is going to be WEIRD. Try out any of these after "cool!" and see if they wouldn't make you feel uncomfortable to ask or be asked.

• What's your family like?
• Are you happy in your job?
• What do you like to do?/ Do you have any hobbies?
• Do you have any pets?
• What would you do with a million dollars?
• What do you think about the political candidates?
• Have you seen any good movies lately?

You may have better questions than I do, and if you do, I bet you're better at medium talk than I am, because these are the kinds of questions I'm thinking of asking.

Since asking the questions I can think of are weird, my next two best choices are to:
a. Say, "great to see you!" and walk away to then hover at the snacks table (assuming I'm at a party with a snacks table.)
b. Talk about myself and hope something that I've just described will connect with them and they can build on it.

Both strategies work just fine, and I make it to real friend zone with plenty of people, but that middle zone is tough and awkward. Good medium talkers, how do you do it?