Kathleen Hanna Corner of St. Marks and 3rd Avenue, across to Tompkins Square, around the park with a stop at Odessa. One of our favorite Riot Grrrls is living a peaceful post Bikini-Kill, post-Le Tigre existence with her Beastie Boy husband in the East Village. We’d obviously talk about blogging.
Yoko Ono Skip The Dakota altogether and head to more peaceful environs, encircling the Cloisters far up on the Upper West Side. We imagine this conversation to be a real-life interpretation of Ono’s Twitter stream: random thoughts and vague directions punctuated by knowing giggles. We could also try out our primal scream.
Ezra Koenig St. John’s Cathedral near Columbia University, up Amsterdam to the Columbia campus and down Broadway with a stop at Absolute Bagels on 107th. We’d talk interior design (Seriously; have you ever been featured in hip domicile-porn mag Apartmento? Thought not.) and hockey, from knuckle pucks to arena songs.
Anna Wintour Times Square straight down to Bryant Park, back up to West 54th for afternoon tea at The London. Her car service supposedly got canceled (ha, right) so if La Wintour ever has to mingle with the plebeians, we hope it’s us. Her Bobness has dry British wit and an encyclopedic mind, two plus marks in any conversation.
Mary Boone 14th Street A/C/E subway stop, up the West Side Highway to Chelsea’s main drag, stopping at Boone’s eponymous gallery on west 24th Street. Chatting with Boone would be like insider trading for art collecting, and just in time for the upcoming Armory Show. After all, Whitney Museum director Adam Weinberg already likened the ride-share program to “one big art project.”
Terry Richardson Model-stalking the streets of Soho, up 6th Avenue and cutting over to the Meatpacking District before a drop-off at The Standard Hotel. Love him or hate him, he’s entertaining as hell. (And again with the blogging!) Terry’s Diary is proof that he gets along with any and everyone — the cast of Jersey Shore, Christina Hendricks, Omar from The Wire…
Julie Klausner Down Broadway in Soho, sight-seeing in Chinatown, then back to stomping grounds in Nolita for carb-loading at Epistrophy on Mott Street. We share a mutual mortal enemy, according to Klausner’s 21 questions with New York mag: “Somebody really shitty who doesn’t eat carbs and hates dogs.” And bad date stories can make even the illest traffic snarl bearable.
David Byrne and Cindy Sherman (together!) A whirl around Union Square, then up Irving Place, skating the perimeter of Gramercy Park before a cocktail at the Gramercy Park Hotel. Our favorite alt-couple is a friendly pair, perhaps more approachable than, say, Lou Reed and his artist amour Laurie Anderson. In our fantasies, Cindy Sherman would share makeup tips. Though, come to think of it, we’re pretty certain Byrne prefers bikes to cabs, ride share or no.
Jon Stewart 11th Avenue at 52nd Street in front of the Daily Show studios, up Central Park West to stroller-friendly brunch territory around 86th and Amsterdam. Look at Stewart’s face: he’s thinking about Obama’s health care bill. What else would we talk about?
Barry Diller The toniest stretch of Museum Mile, down Fifth Avenue from East 86th to East 70th, looping back up Madison for a stop at The Carlyle. The Chairman of IAC is scary successful and could offer some legitimate business advice to the likes of bottom-feeding bloggers like us. Not to mention, anyone who can keep Diane von Furstenberg entertained must have some killer moves.