Slippery sentences

Have you ever had a conversation that was so bad, you wished a 1000 pound piano dropped on your head, just so it would end?

I have.

Sometimes conversations can feel a bit painful for me, and instead of being present, I’m thinking of an excuse to get out of a conversation early.

First off, I’m not extroverted. So I realize good conversations are not going to magically flow out of me. Unless I’m in a great mood and energized, I’m rarely kicking off small talk, flirting or making jokes. Usually I’d rather keep things short.

What would a salesperson do?

I don’t want to suck at conversations for the rest of my life. I’m always going to be an introvert to some degree, but I have wondered if simply acting more extroverted would help. Turns out, yes?

Taking advice from Dale Carnegie, who encourages us to smile a bit more, use names, encourage others to talk about themselves’ and talk in terms of the other persons interest’. You can roll your eyes at the unbridled American optimism, but it’s generally good advice to be more personable, approachable and likable.

For me, this was interesting but ultimately felt unnatural and exhausting. The main thing I took away was the importance of suspending your ego a bit. We naturally like to think we are the main character.. and that doesn’t always lead to great conversation.

100 first date (conversations)

More recently, most of the longer conversations I’ve been having outside of work has been on dates - with strange women I’ve never talked to before.

Aside from the whole generational burnout from online dating thing, I was having a couple of issues.

  1. When I matched with someone on an app, rather than having a proper conversation in the app, I was very quick to try and organize a real life meeting. I would say something like hey, let’s grab a drink!” Sometimes that worked, but other times it was a dead end.

  2. Once I met someone IRL, although I think of myself as a pretty good listener, I found conversations were getting stuck a surface, superficial level, and not that interesting. Was it them? Was it me?

What was going on?

Something to grab onto

Do you like footy.” Uh, I don’t watch it so much.” Dead end.

If I think back to some of the stuff we were talking about, I realize I was giving very little details about myself. I wasn’t taking a position, having a strong opinion or sharing any truth’. Probably because I wanted to come across as likable, and not get rejected. I’m not alone with this either. Scroll through any dating profile from any gender, and it’s all ice cream’ and clean sheets’.

My conversations were suffering not only from a lack of affordances but a lack of … myself.

The truth is a bit grittier. There’s a bit more texture, color. There’s more for someone to grab onto. That’s what I needed! You know, I don’t think I ever really got’ footy, and I feel a bit guilty about it. I’ve been to some games but I can’t get as excited as everyone else. I’ll tell strangers I support Collingwood, but I can’t even remember why I supported them in the first place!”

I feel a bit embarrassed sharing it. And if they are a die hard footy supporter, they’ll find it a bit weird, and I might get rejected for it.

But that’s good, because that’s me. And hopefully they say.. Oh that’s funny, you know what, me too!

September 3, 2022

New York