Last year I had an article in the New York Times—a personality piece about my then-dude that I wrote for their "Modern Love" column. While it was somewhat shocking to see my (real) name in that most-hallowed paper, it was more disconcerting to see the illustration that accompanied it: a watercolor portraying an eerie likeness of me and an eerier likeness of my dude. How did the illustrator guess what we looked like? Was he stalking us? My curiosity piqued, I asked my editor at the Times about it, and he directed me to David Chelsea, who happens to live in Portland. David's been a working artist for 28 years. He got his start in high school, illustrating for the Portland Scribe, a precursor to the Willamette Week. He went to art school in New York and lived there until 1995, when he and his wife moved back to Portland for more elbowroom and to start a family. These days, David affords his swanky Irvington lifestyle with two regular gigs: He's done the calendar for the New York Observer every single week since 1995, and has illustrated "Modern Love" since 2004. Like many illustrators, Chelsea's true passion is comics, and his early-'90s graphic novel, David Chelsea in Love, was reprinted in French last year.

How much time does it take to illustrate one "Modern Love" column?

It's a solid two days out of my week. I get the manuscript on Friday and send in six thumbnails by Monday. They get the finish by Thursday and it runs on Sunday.

The piece you did for my column was creepy in its verisimilitude. Do you Google people?

I did Google you, but the photos weren't very useful as the piece called for you to be clothed and seen from behind.

Any columns that have been particularly challenging? It's challenging coming up with new ideas because a lot of the same topics keep coming up. I don't like to recycle, but there's only so many changes you can bring to "birth mother finds long-lost kid."

Was there a column that was particularly fun?

A couple of weeks ago I illustrated one that involved a woman who'd just been divorced, and she volunteered for Katrina recovery, and the magnitude of the suffering there sort of put hers in perspective.

What was the illustration?

I drew her standing in the midst of a house that's collapsed on her, but she's been saved because there's a heart-shaped window in the attic. That was a chance to recycle a classic bit from a Buster Keaton movie.

What's the "Modern Love" piece you're working on now?

It's another birth-mother-finds-kid-after-13-years story.