This weekend, I finally met Gregg.

Gregg is Drew’s ex-boyfriend, with whom he spent five and a half legendarily tumultuous years. Their relationship ended last summer, and Drew has tried to stay friends with him since then. Why, I’m not sure.

Usually when Gregg’s name comes up among Drew and his friends, it’s followed by the words “is very messed up”. This is a bit strange from people, including Drew, who claim to still be his friends. When I’m describing a friend of mine to someone who has never met them, I might use some negative or critical words, but only to prepare the person for my friend’s misleading surface traits. I might say, “She comes across a bit abrasive at first, but she’s really very nice underneath.” Or “he tends to make some off-color jokes, but he’s just kidding around”. These are my friends, after all. They might not be perfect, but there’s always a “but”. With Gregg, on the other hand, there never seemed to be a “but”. “Greg is very messed up” was usually the beginning and end of the description.

All of that made me very curious to meet Gregg. Clearly, his personality quirks were too numerous and/or bizarre to list in detail. “Messed up” was a sign of a person who was very, well, messed up. But the fact that all these people were friends with him anyway, let alone that Drew spent the better part of his 20’s dating him, made me think there must be a “but”. I was sure Gregg had a sparkling sense of humor or a soft spot for helping the less fortunate. And now that I’ve met him, I can say with certainty:

Gregg is very messed up.

I like to think I’m a pretty good judge of people, that I can see through their facades to the real them fairly quickly. But Gregg is extremely complex. With or without my personality x-ray specs, Gregg is going to take some work. So far, though, there are a few things I can say about him:

1. He wears sunglasses all the time, even indoors. I have no idea what his eyes look like.

2. Gregg goes for shock value with his humor. He thinks it’s easiest to score with off-color jokes.

3. He thinks he’s extremely funny.

4. He’s somewhat funny.

5. He’s EXTREMELY gay.

Gregg was clearly very nervous to meet me. But he picked up fast on the fact that I was just as nervous, and that put him a little bit at ease. When we were first introduced, there was a long, uncomfortable silence. After that, Gregg got a little chattier. Gregg’s first icebreaker was to point out how weird it was to be a childless gay friend at a pool party for four-year-olds. Everyone stares at you like you’re a child molestor, he observed.

I checked around. Nobody was staring at either of us.

Gregg nonetheless repeated this observation to every new person who came over to talk to us. It was his idea of a joke, and apparently, of a good joke. I realized this was Gregg’s schtick. He found something to say that he thought would make people uncomfortable, then repeated it to everyone he could find. At one point, a woman came up to us and said something that sounded like, “Is this where the young Jews are hanging out?” (Neither of us is Jewish.) I assumed I misheard her, but when she walked away, Gregg had heard the same thing, and he couldn’t wait to play up his “outrage”. “Did she call us Jews?” Within ten minutes, he had told the story at least five times, railing about the anti-Semitism pervading the party.

Once I had talked to Gregg for what seemed like an appropriate amount of time, I was anxious to move on. Drew stayed with Gregg for five and a half years. I was ready to leave him after five and a half minutes.

When the cake came out, Gregg turned to me, in front of Drew, and said, as if to prepare me for an indescribable horror, “Uh-oh, Jerry. Have you seen Drew eat cake yet?” Drew quietly laughed off the jab at his eating habits. It explained a lot about how their relationship must’ve worked.

After the party was over and Gregg had left, everyone wanted to know my impressions of him. Not wanting to seem like the jealous boyfriend, I think I said something along the lines of, “He seemed okay.” The general concensus among everyone was that Gregg was on his “best behavior” all day.

That horrified me.

That was his best behavior? What I had seen was a passive-aggressive, insecure, hostile, obnoxious, unfunny, self-loathing, messed-up jerk.

But he did have nice sunglasses.

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