Recently, several articles have addressed the nuts and bolts of how to have more engaging connections and conversations. I read these eagerly (it used to be so easy, why isn’t it anymore?). Health writer Jane E. Brody includes a short piece of advice in her latest column for the New York Times. Although the column is technically about becoming a mentor (or finding one), the advice seems universal: “The key is not being interesting,” author Marc Freedman tells her. “The real key is being interested — being present and paying attention.” Release the desire to seem funny and smart, he said, and listen instead.
It made me think of a Cup of Jo essay I read last fall, in which the writer and director Lisa Rubisch shared her own personal “Social Anxiety Cure-All”: remembering that the only social basics are to be curious and kind. “You don’t have to be the smartest in the room,” she writes. “All you have to be is curious and kind. No one can fault you for that.” Or, if that feels too difficult (what should you say that’s both curious and kind??), consider the 2017 study about how people like people who ask them questions. In an interview last fall about how to ask better questions (and to have better conversations), Fresh Air’s Terry Gross said that her No. 1 default prompt is simply: “Tell me about yourself.”
Sometimes when I’m talking with someone, I get distracted by the concern that I’m not being funny or interesting enough, and I miss details. It’s not going well, I think, which in turn makes it not go well. A friend of mine once asked a group of us what the biggest regret of our 20s was. It was a fun and a hard question to think about. We all went silent for a while. Some people mentioned the relationships they were in for too long, or the jobs they wish they’d left sooner. I said I regretted all the details I’d missed when I was drinking. I bulldozed over a lot in my attempts to entertain. It wasn’t all bad, it just feels like something different is called for now.
What about you? What are your biggest regrets? Tell me about yourself.