Lunch Dates

Dear Sugar (CherylStrayed.com)

Lunching with Dear Sugar’s Cheryl Strayed: On Love and Bedbugs

We rushed into Midtown’s fancy french bistro Cognac, already five minutes late to meet Cheryl Strayed, the recently (or not) outed authoress of the Dear Sugar advice column. On Stephen Elliott‘s site The Rumpus, Dear Sugar has blossomed in the two years since Ms. Strayed took it over from her predecessor, Steve Almond. It went from snarky relationship advice to something much more personal…and universal, under the 43-year-old Portland author’s touch.
Dear Sugar always answered her readers’ questions with anecdotes from her own life, but instead of over-sharey, Dear Sugar became something of an online Oprah. She’s been there, honey!

She was only in town for the evening, to read selections from her new memoir, Wild, at the Powerhouse Arena in Brooklyn. The New York Observer had approximately 1 hour to pick the advice queen’s mind…but we created a catch for the Portland native. Instead of answering for a general audience, our questions were specific to New York (or at least a major city).

To be honest, we spent all night thinking of questions that Ms. Strayed already hasn’t answered: Facebook relationships, money, jealousy, infidelity. We had only been able to come up with one. But it was a dozy. Read More

Nightlife

Illo: David Saracino

The Wee Hours: A Reporter Goes from Soft Openings to Hard Time

The Observer was arrested last Friday for entering the subway through an emergency exit. We were cuffed, frisked and led by a police officer through the station. Commuters with tote bags stared.

We found ourselves in a holding cell in the Union Square station precinct with a man named Felix, who had been brought in for sharing a MetroCard with his pregnant wife. Two others came, and then left with desk appearance tickets.

But we would be joining Felix in central booking. We had a warrant, an open container summons, a relic from a summer in 2008. Ah, right: the G Train, with that girl, drinking Sparks out of a brown paper bag. Read More