So, of course, all of Washington wants to know who the guy — with whom Kaling has a text-heavy relationship that culminates in a single night o’ passion — is. But Nancy Drew-ing who this “Will” really is won’t be an easy task.
Kaling’s obscured her D.C. boo’s identity, per notes elsewhere in the book, dubbing him “Will” (there are at least three Williams on the White House payroll, according to salary disclosures, but we can assume that his name has been changed.) In her description, he’s a tall, blond University of Pennsylvania graduate who wears glasses and likes hiking.
At least some of these details have to be made up. But others, like the fact that Will travels “everywhere” with the president, including on jaunts to Kaling’s home base of L.A., are central to the story and probably the real deal.
According to the tale relayed in a chapter titled “One of the President’s Men,” the pair first met when then-top White House aide Alyssa Mastromonaco (whose alias in the book is Sarah Fisher) invites Kaling to the Waldorf hotel in New York to meet the president. (We know it’s Mastromonaco because Kaling described that meeting to us at the White House Correspondents’ Dinner.)
Flirty texting and Facebook stalking between the writer/actress and the hunky staffer ensues, and once in the White House orbit, Kaling scores an invite to the state dinner for the French president in February 2014. Although the pair eventually hook up when Will travels to L.A., they’re ultimately too busy to pursue a relationship, though Kaling suspects she made “more of an effort” than he did.
If nothing else, the story illustrates just how much of an advantage a White House staffer has in wooing a politically aware Hollywood starlet. Aside from Will’s good looks, he impresses Kaling with heady ammo that only access to the president provides: a birthday note written on White House stationery, texts from Air Force One, an invite to privately tour the White House.