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