In February of 2009, my roommate Steve was reeling over the end of a long, serious relationship. His sadness surprised me because he had considered ending it for months, but when the moment had finally come and indefinite singlehood was staring him in the face, he couldn’t help but think he’d made a terrible mistake.

He did not handle it well. Some would say he handled it terribly. And by some, I mean all. He could barely even function. He often sat motionless, staring into the distance, which was usually a wall.

One cloudy Saturday afternoon, Steve and I were sitting and talking with our other roommate Reimar. Or, more accurately, Reimar and I were talking while Steve stared into the distance.

“Steve and I went out for dinner the other day,” said Reimar, “and for some reason I was feeling charismatic, so I started chatting up the waitress.”

Reimar explained to her what had happened to Steve, that he was out of sorts because of a breakup. She turned to Steve, examined him for a moment, and comforted him.

“You’ll be okay,” she said. “You’re pretty.”

I laughed and told him that I would call him “Pretty Gray” from now on, because his last name is Gray, and because “Pretty Gray” sounds like pretty gay, which describes a lot of things that Steve says. You see, Steve often says things that somehow sound good in his head but are easily misinterpreted outside of it. An honest thought may sound awkward, a candid request may seem harsh, or a random comment may come off, well, pretty gay.

“I’m going to make a Twitter account called @prettygray,” I joked. “Every time you say something ridiculous, I’m going to post it there.”

I had good intentions, I explained, because allowing him (and all our friends) to read what he says would help him realize how ridiculous he sounds at times, hopefully speeding up his emotional recovery in the process. At this point it was unlikely that this was going to be anything more than an amusing idea, until…

“Today the skies are gray. Like me,” said Steve, interrupting the silence.

Reimar and I turned to see Steve staring listlessly into the distance, which this time was a window. I reached for my phone to make a new Twitter account.

As the months passed, his depression became less pitiable and more pitiful. During our occasional heart-to-hearts, I began quietly judging him in my mind.

Man, I would never be this worked up over a girl, I thought. Get over it already.

After all, I once got over a three-year relationship in three days, a fact I’ve told more people than my own name. Meanwhile, Steve had been sulking for six months, and every day seemed like he was broken up with all over again.

But then two things happened.

The first incident happened when I broke up with a girl I was dating and, for the first time in years, I had a hard time moving on, even though I wanted to end it. No matter what I tried, there was nothing I could do about it. This, I remembered, was what it felt like to be emotionally helpless.

The second incident should’ve been just another phone call.

To give you some context, I had been dating a girl for about three weeks and things had gotten serious fairly quickly. I was in love. So in love, in fact, that anyone who had a conversation with me knew about it, including the security and parking attendants of my office building.

One night we had a phone conversation that lasted into the wee hours of the morning, and by this point we were both so delirious that we weren’t really talking anymore. I don’t remember exactly what I said next, but somewhere in that sleep-deprived sentence I accidentally called her by the name of the last girl I dated.

“Did you just call me [the other girl's name]?” she asked. Her tone was serious, her voice alert.

I remained calm and tried to play it off, but she knew what she heard, so I apologized.

“I’m gonna go to sleep,” she said, obviously bothered, and hung up on me.

I wish I could say that I knew that this wasn’t as big a deal as it felt, that I remained calm and went to sleep, which tells you that this is exactly what I did not do.

Instead, I was convinced that I had just punched the girl of my dreams in the throat. I felt like I had to do something before I slept—ANYTHING—or else our relationship would never be the same. So I came up with what I thought was a brilliant idea: email all my friends, explain to them what happened, and ask them to flood her inbox with reassuring notes, letting her know how crazy I was about her. It seemed like a good idea at the time.

An ex once told me that I like to create movie moments, so you can imagine how marvelously I thought this was going to turn out. I went to bed feeling quite proud of myself. I don’t remember the exact moment when I realized this was a bad idea, but I’m pretty sure it came in the form of an instant message.

“Did you really just send that email?” wrote one friend. “You gotta stop flying on your emotions and just stop and think.”

She was right, of course, and she wasn’t the only one who let me know that I may have made the situation worse. I quickly sent out a follow-up email to abort my idea, but that was only the beginning of that terrible day, and it didn’t help that I felt like many of my friends were judging me.

One thing was for sure: I did not like being judged, even though I agreed I’d made a mistake. It’s not that I didn’t want people to tell me I was wrong; I crave honesty more than anything. It was the condescension I couldn’t stand.

See, there’s a difference between being an honest friend and being a judgmental one. You can tell a person that you disagree with their decisions without assuming you have any idea what that person is going through, and without being certain that you would do anything differently. We aren’t as rational as we think we are, and our decisions are influenced by so many subconscious factors that even when we try to explain why we did this or that, we’re mostly wrong. On top of all this, when you assume you would have done things differently than someone, you inadvertently make that person inferior to you. After all, if you would’ve acted differently, why couldn’t they?

I realized that this was what I was doing to Steve. Just because I’d experienced breakups in the past, I assumed that I knew what he was going through. And just because I’d gotten over those breakups quickly, I expected him to also. Worst of all, because he wasn’t meeting my expectations, I belittled him in my mind. And yet this is what we do to people every time we judge them.

It takes so much effort to be openminded and understanding and forgiving and accepting, but it matters. Life, after all, isn’t black or white. More often than not, it’s pretty gray.