The Dying Art Of Difficult And Awkward Conversations

A few years ago, I was trying to sleep around 2:00 in the morning and the people in the apartment next to me were making a racket having some kind of party. As I lay there in bed, I contemplated my options and waffled over whether to get up and knock on their door. I believe in the right to party and make noise, but as it got toward 2:30 or 3:00 I decided enough was enough.

As I threw on some clothes, I worked myself up to a state of dread and fear about the conversation. I had never met the neighbors, who had moved in not that long before. I pictured energetic partying people, angry at me for interrupting them. I pictured large guys answering the door and looking at me like I was the worst person ever. I pictured years of living next door to these people who regarded me as an asshole. I pictured them finding the smallest reason to complain back, as the years wore on.

I crept out into the hall and knocked on their door. A woman answered, with a man standing a bit behind her. They were smiling. I explained, nicely, that I was trying to sleep. They were extremely apologetic. They hadn't realized how the noise would carry. They expressed concern and kindness. They immediately quieted down, and the next day they left a ten dollar Starbucks gift card and a note on my door. I wrote them a thank-you note.

And as I have on other occasions, I found myself wondering at the power of talking to people in person and the difference between what we imagine and what is real when it comes to certain kinds of difficult conversations. I have had many similar experiences, where reality confounded expectations. It's a platitude that open honest conversation produces good results, but it's also human nature to want to shy away from conflict. And platitudes are often stupid. But in this case there's something to it.

It's not always true and there are assholes everywhere. But if you have a problem or something you need or want, and you express yourself with respect and kindness, it's amazing how many people will be respectful and kind right back to you. 

I would go even further and say that negative or difficult conversations often draw people closer together. I don't know if you've had this experience where only someone's judgment or need conveyed to you the depth of their concern. When people are a hundred percent live and let live, you can't get any grip on where you are with them.

I'm not one of those people who are always complaining about "kids these days" and I think generally speaking the younger generations are wonderful and unjustly accused of all kinds of ridiculousness. I don't buy into the idea that their desire to make the world a better and more just place speaks to some kind of weakness on their part.

But I do think that all of us are getting even more reluctant to have difficult or awkward conversations, probably for a range of reasons, some of which involve the internet. Sometimes out and about, I see people waiting and waiting for their needs to be acknowledged -- by a stranger or a service person -- seemingly reluctant to speak up and say "Excuse me, can I get some help"?

I don't know if you've noticed this, but in women's bathrooms in public places, women will line up behind one another, entering only the stalls that someone is coming out of, and leaving a bunch of stalls open and unused, because they don't want to be "that person" who is either knocking, or trying the door, or looking for shoes under the stall, to see which ones are empty. Because it's awkward.

Somehow I feel like the extra negativity we feel when we hear these things by email or virtually has infected our impression of how we'll feel when we have these difficult conversations in person. It's tempting to think that bad news should come virtually, since the person can react privately and won't be put on the spot. But I think that's a mistake. When I have bad news to convey, I feel like conveying it in person just passes along so many human emotions along with the news, it can't help but be made better.

I remember a long time ago when I was in high school, I had these two teachers. One was relentlessly positive and always told us the nicest, most supportive things. She was like a cheerleader for students. The other was difficult, and caustic; she was the faculty member in charge of the literary magazine and when she thought students were being stupid or lazy she would tell them so in no uncertain terms.

I remember that when I applied to a summer arts program, I had to get some letters of recommendation. And I was so much more comfortable asking the grouchy teacher than the supportive teacher. Because the supportive teacher was so supportive -- I had no idea what she really thought of me, or what she really thought about anything. The grouchy teacher, I knew she thought I was smart and talented, and I knew she thought I was imperfect, and we were good to go.

Difficult and awkward conversations are difficult and awkward. But especially when you have them in person, they're often OK. As we get less comfortable being awkward together, I hope they don't disappear entirely.