The Curious Case of ‘‘Comfortably Smug’’

Photo: Joshua Allen; Grooming by Bryan Lynde

He’s read every Sex Diary and posted 1,449 comments on He wrote a Diary of his own: “The Self-Obsessed, Emotionally Detached Hedge-Funder,” which detailed a week of obsession, rough sex, and Ambien. He’s also had amorous encounters with two former Diarists. And he calls himself “Comfortably Smug.”

How’s your persona differ from your real personality?
I’m not as blatantly an asshole in person, but I still have asshole tendencies.

How do you have the time to write so many comments?
Lots of Adderall. I squeeze it in during lunch, or if I’m running somewhere I check on my phone in the cab. I’ll get five comments done in three minutes.

Why write a Sex Diary?
I said I bet I can submit one that was better. So I did. I wrote down every thought that goes on in my head that I wouldn’t tell people. I left myself really vulnerable, especially given the corrosive responses I’d left to other people. Mine was the first Diary to break 100 comments.

What did you think of the comments?
It became apparent how much I was abusing pharmaceutical medications at the time, to numb my experiences. Also, it was brought to my attention that I was reenacting my own negative relationship experiences with other girls. I went back and replied to every commenter.

What was your previous relationship like?
Agonizing—being in love with someone who wasn’t in love with you, and being addicted to that pain.

How did you meet the two other Diarists?
They e-mailed or Facebooked me. It was fun. We live in the same place and let the entire city know everything about our sex lives.

And your current girlfriend?
My girlfriend was an avid reader of She wrote me an e-mail asking if I’d like to meet for a drink sometime. She thought I was an interesting character and didn’t believe I could be real. That’s probably the motivation for almost all the people I meet. They don’t believe I actually exist.

Given your online persona, was she hesitant to start dating?
Yes. She was incredibly paranoid about me having diseases and being an asshole. Ironically, I made the first move to say that I wanted to be in a committed relationship, and she said no. Which was, in hindsight, pretty awesome.

The Curious Case of ‘‘Comfortably Smug’’