authenticity

how to have better conversations

Christian Schad, Café D’Italia, 1921

I’m drawn to a dark aesthetic. Morally gray characters fascinate me, and I love a good redemption plot. I find melancholy very beautiful. Sad songs stay with me longer than upbeat ones. I like people who can straight up say, I’m feeling sad today or life is hard. Because it is, and I think talking about why it’s hard and why we self-sabotage and how to deal with complicated emotions and relationship problems is worthwhile and fun.

Despite my attraction to melancholy, my average mood can be described as “calm optimism.” My life is pretty stable, and I have routines for the things I care about: writing, exercising, meditation. I read somewhere that in order to do crazy shit in your art without losing your mind, you need to have a well-organized life.

When I meet someone for the first time, I like to gauge how much “melancholy” they have in them. A dash of it makes for interesting conversations. Susan Cain calls it the “bittersweet”:

A tendency to states of longing, poignancy, and sorrow; an acute awareness of passing time; and a curiously piercing joy at the beauty of the world. The bittersweet is also about the recognition that light and dark, birth and death—bitter and sweet—are forever paired.

I’m suspicious of people who seem eternally cheerful and just fine with everything. A sense of humor is important, but a sense of humor without being able to get real makes me think they are hiding something.

Someone I recently met said this, and it struck a chord: when you feel drained after a social event, it’s likely because you weren’t comfortable being your full self with the people you were with. If you think about it, this makes sense: it’s very energy-consuming to suppress a part of you or be anyone other than yourself.

When I think about the social events that haven’t drained me, two things are true: 

1. The conversation veered into territory I really care about. I think everyone has a thing that preoccupies them, that they can’t stop thinking about, that they have to talk about in order to feel like their authentic self, to walk away feeling seen. It’s what gives them energy, the conversational equivalent of a buzz. For me, it’s relationships, dating, attachment, creative struggles, etc.

2. The amount of talking was fairly balanced among participants. When one person dominates, others are holding back what they want to say. Even a one-on-one interaction can be exhausting if you’re made to listen to the other person talk on and on about their stuff. And because we want to be nice and accommodating, we sit there and nod and ask more questions, all the while feeling utterly drained.

Essentially, the less you care about a particular topic, the more exhausting it is to talk about it. To have better conversations with anyone, it’s important to ask genuine questions. You have to really want to know the answers. Sometimes we fall into the trap of asking our friends about stuff we don’t really care about. I’m guilty of this. If I know someone has a personal project that they’re invested in, I’ll make sure to bring it up even if it doesn’t interest me. And so I lay the trap for myself of hearing them go on and on about it, leaving me totally sapped. I’m trying to get better at asking people about only the stuff I care about. Because if they care, too, they’ll want to talk, and we both walk away feeling like we had a nourishing conversation. 

Last year, I went on a date with someone who mentioned that the reason he broke up with his ex was because she was dealing with a lot of personal issues. She basically hated men, he said. My eyes lit up. Now, that’s interesting. I want to hear more about that. Unfortunately, he couldn’t articulate her point of view (it’s nice when someone can articulate a perspective they disagree with), and I found myself unable to open up to him because I felt I might get similarly judged for having “personal issues.” 

Recently, I played a round of We’re Not Really Strangers with a good friend. We learned a new thing or two about each other, and I realized that many of the questions in the deck are ones I could’ve easily asked him over the many dinners we’ve had over the years. We don’t need a game to ask these questions and open up, but somehow, we don’t think to ask the people we think we already know what question they’re trying to answer most in their life right now or what’s a dream they’ve let go of. But asking these deeper questions gives them the chance to surprise us.

When I think about the things that most fascinate me, they mostly fall under the umbrella of the bittersweet, the slightly tragic, slightly melancholic, yet hopeful essence of being human. And I fully embrace that. I’m less afraid now to bring up topics that might scare people away, that might make them think I’m a little crazy (aren’t we all?). I’m O.K. being a little selfish in conversations. You need to be selfish. It’s like a tug-of-war. If you’re not pulling in your direction, then you’ll never reach that middle ground of mutual interest and connection.