I just watched last night's Gossip Girl episode ("It's a Wonderful Lie"), the one where Vanessa has a gift certificate to Grimaldi's ("I'm thinking double pepperoni"). For all you non–New Yorkers, yes, it's a real place (you can read all about it here on Slice), and, yes, it does offer gift certificates (I called to make sure).
I agree with New York magazine's recap assessment—Vanessa would totally be a "Di Fara diehard." All the way. Why? Vanessa sucks. She's annoying and oppressively self-righteous in that way that only certain chip-on-shoulder Brooklynites can be. If you were unlucky enough to befriend her—or worse, date her—she would totally twist your arm, reverse-snob you, and schlep your ass all the way out there. "OMG, Nate! I totally know this little place that's hidden and has, like, the best pizza ever! None of your Constance Billard or St. Jude's friends would be caught dead there." And then she'd secretly judge you if you grumbled about the long wait or what a mess the dining room was.
Where the Rest of Them Would Eat Pizza
My first thought: Blair wouldn't eat pizza. But then an evil little elf reminded me that, "Yes, she would! She would just throw up afterward!" I think any generic Ray's pizza would do for that. Loaded with all the crap the various Ray's put on their pies.
Dan is overearnest, smug, and unbearable. Like a lot of the folks on Chowhound. Which is why he, like a lot of the folks on Chowhound (and like Vanessa), would be a Di Fara fan. He's also writing a pretentious short story or a "Shouts & Murmurs" piece about the Di Fara experience in hopes of getting it in the New Yorker.
Serena has a kind, goofy side, so she'd be comfortable slumming it in pizzaland. But she's totally high-maintenance, so only Una Pizza Napoletana will do. Then again, Dan could puppy-dog-eye her into a trip to Totonno's (it's deep to wander Coney in the off season), after which she'd reveal her vulnerable side and wonder "Why can't we always be like this?"
Nate is totally dull. He gives little thought to what he eats and just grabs an unimaginative slice of pepperoni at whatever pizzeria is closest. (Unless Vanessa drags him to Di Fara.)
Chuck Bass eats at whatever pizzeria is still open after he gets out of his burlesque parlor or the strip clubs. Since the New York burlesque scene seems to be centered on the Lower East Side, let's say Rosario's. It's open till 5 a.m. If he's cruising the West Side strip clubs, let's say 99¢ Fresh Pizza, open 24 hours.
Rufus would make homemade pizza (with some sort of expensive Spanish ham, imported "00" flour, and buffalo mozzarella) and then guilt-trip Dan and Jenny into staying in, listening to him blather about Lincoln Hawk and Lisa Loeb. Lily van der Woodsen would show up unexpectedly, have a bite of pizza, swallow with a pained expression, and then make a grandiose statement.
Additional reporting by Kerry Saretsky