Instead, it’s perhaps the most fragmented and phony I’ve ever been.
While Lloyd tells me why he doesn’t like Olbermann, I also start to really fall for him. He’s so able to laugh at himself and the moment he does the most searing imitation of Howard Stern mocking him in a very put-on affected voice, I think: This is the guy. When I tell Olbermann that I can’t see him anymore because I’m going to be dating Lloyd exclusively, Olbermann replies, “Good grief, my mortal enemy.”
Lloyd and I eventually do break up, but he treats me better than anyone up to this point in my life. There are so many hilarious moments during the relationship (I mean, the guy was good friends with that most scathing wit of all, Christopher Hitchens), and there are several inadvertently hilarious moments, too. Like when he takes me to the White House Correspondents’ Association dinner, and at the MSNBC after-party we run into disgraced governor Eliot Spitzer. After listening to me prattle on for a few minutes, Spitzer turns to Lloyd and says, “She must be a handful.”
Or when we go to a Midtown bash where Gerard Butler is the guest of honor for How to Train Your Dragon. Having once joked with Butler after he came onstage at the Comedy Cellar to shout down a rude heckler, I really thought I knew the room and that we were pal-ish. Boy, did I ever read it wrong.
Thinking he was Mr. Laugh at Himself Crude-Sense-of-Humor dude, I way too familiarly reference something about a Post story portraying him as a womanizer. I think I am teasing. This is the most fatal mistake that people make status-wise with showbiz types. You never, ever try to level up by saying anything remotely negative. Ever. Never. Ever. Bad move.
Butler proceeds to curse me out and demonstrate how shitty such allegations are. “What if I said to you, ‘Wasn’t that you who I saw getting fucked in the ass in a back alley?’ ”
I pause, think for a minute, and respond with a big smile, “Yes—that was totally me!”
Butler just shakes his head and walks away.
After Lloyd and I break up, it’s not long before I am back to my old love-triangle ways and dating Olbermann again. When I do it this time, though, I dangle this fact to Sorkin, who replies, “I’m glad you had a good time with Keith, but I’m better.” Olbermann, who initially tells me he likes Sorkin, reverses his opinion severely after The Newsroom premieres and words he has said to Sorkin are used in the show.
There are several surreal moments during this era. I’m aware, for instance, that Sorkin is spotted out with Kristin Davis (who played Charlotte on Sex and the City) around the time I am also seeing him on and off every few months. When he invites me to his mansion above the Sunset Strip to watch The Newsroom premiere with him, I cockily text several girlfriends, “I’ve never felt more Samantha!”
Or when he creates a character in The Newsroom based on one of our dates where I bemoaned to him over dinner having to excoriate a celebrity as part of my job.
“I have to write this takedown piece on one of those Real Housewives, Bethenny Frankel,” I had told him. “But I really like Bethenny. I respect her. She sent me a freaking vegan-muffin basket one time, for crying out loud. I tried to get out of writing it, but I can’t.”
It was a very meta conversation to have: trying to explain the heartlessness of your job in celebrity gossip trafficking to someone who has been the victim of said gossip.
“What exactly is a takedown piece?” Sorkin asked.
I explained how it is a faux-populist, folksy, “we’re not going to take it anymore,” tabloidy, STFU rant for whatever winged creature of the moment has flown too close to the sun.
The celebrity in question usually has done three recent things that are not so good. And maybe another reporter has an anecdote or something. And you know how journalism works, don’t you? Three things make a trend. A trend—or a takedown piece. In explaining this, part of me felt a weight off my shoulders revealing the stomach-twisting paradox of life as a gossip peddler who also happens to be, very inconveniently, not a short-game sadist. There was also a part of me that was glad he could get a glimpse of how the other half lives—when the other half is trapped and needs a fucking paycheck.
“It’s . . . you know . . . it’s a takedown piece,” I explained. “That’s what we call them at the Post. That’s what we do. It’s a formula where you talk about all the things the public is pissed off about. But sometimes it just feels toxic when the controversy is more manufactured than anything. But I can’t get out of writing it. I really tried.”
“So . . . it’s just bitchiness?” Sorkin asked. “What if you suggested five different alternative stories?”
I laughed.
“It’s the Post,” I repeated. “Have you ever read the Post?”
Later that night at the Four Seasons, completely apropos of nothing, I turned the conversation away from me and tried to focus it on him. I have this bad habit of offering unwanted advice, ever so arrogantly, on exactly how I can “help” someone. You know, because I’m so self-actualized and shit. Both my parents are therapists. I’ve been through a lot of therapy. So you can see where my heart lay. Sorkin interrupted my rambling.
“Don’t try to fix me,” he said.
I eventually, of course, wrote my stupid story on Bethenny. It comforted me somewhat that she is a very smart, very savvy woman and knows exactly how the game is played. Sorkin emailed me later from LA about the role our date played in an upcoming episode of The Newsroom.
“THIS CHARACTER IS NOT YOU,” he said right off the
