So instead of going deep-cut, I will only relay the highlights of this love triangle—and leave it as the final word on the matter.
Before I do, though, I suppose I should explain how I even met all three of these guys in the first place, as I’m by no means normally lounging at the Chateau Marmont or wherever the hell A-listers hang.
So I need to go back a few months to before I finally got sober, when I was a party-hopping maniac, often accompanied by my favorite companion: the comedian Wayne Federman. (If you google him and he looks familiar, you may know him as Garry Shandling’s brother in The Larry Sanders Show or from his arc on Curb Your Enthusiasm or as being the guy from all those Judd Apatow movies. Incidentally, he’s utterly fucking hilarious.)
Wayne and I had a very brief flirtation, but, in the end, the chemistry was off. We came to call it a whirlwind forty-eight-hour romance.
“What do you think is a bigger disaster,” I asked him afterward. “This date or the Titanic?”
“Number one, the movie Titanic,” he said. “Number two, this date. Number three, the actual Titanic.”
And that’s how we became friends.
When I was at my lowest, Wayne always made me laugh. In the months before quitting drinking, I told him how scared I was because I had gotten back test results for an irregular pap smear. Instead of indulging in my self-pity or piling even more anxiety on top of my own, he went totally deadpan—and provided a hugely cathartic laugh.
“Wow . . . that is exciting,” Wayne replied. “This could be it for you.”
Even remembering it now gives me this deep sense of relief that only the darkest of comedy can ever provide.
Wayne and I went to SNL after-parties together and watched as Kristin Wiig did karaoke at 4 a.m. at Sing Sing and had several wild nights at the Comedy Cellar. During one of these, he watched as I had the world’s most awkward encounter with John Mayer.
Buoyed by alcoholic confidence, I asked Mayer what he was doing after the show.
“I don’t know,” he said. “Maybe I’ll be waking up next to you.”
When I watched Mayer onstage, I quickly sobered up as I realized he was referencing me being in the crowd.
“Page Six is here, by the way,” Mayer said. “So I’d like to tell everybody that I just fucked, um, Kate Hudson, yes, using—using Megan Fox’s hand. I thought that was quite crafty of me.”
After quickly downing a few beers to have the nerve to approach him after his set, I watched as his entire demeanor changed. Mingling with Dave Chappelle and Jeremy Piven, I waited for my opening—and went for it.
“So, uh, could I get your . . . info?”
He glared at me.
“Why,” Mayer asked, “are you still talking to me?”
And that was that.
But with Wayne by my side, the humiliation never felt quite as intolerable as it might have alone.
As soon as I got sober, Wayne noticed the change in my outlook overall. One night at Carolines, I told him how I was sick of acting like this groveling low-status person all the time, and that I was going to quit doing it.
“Actually,” Wayne said, “that sounds like an excellent idea.”
Cut to the first few months of sobriety.
During this time, I am assigned multiple stories on the film The Social Network. When I interview the movie’s famously mercurial producer, Scott Rudin, I keep the pledge I made to Wayne, and at the end of the call, instead of gushing all over Rudin as I might have in the past, I end the call by saying, in a monotone, “Well, good luck.”
I get a concerned call a few days later from Rudin’s assistant asking if there is anything else I “needed for the story.” Amazing what just a little bit of projection of worth does for your status. After the piece publishes, I call Rudin and ask if I can get on the list, plus one, to New York Film Festival’s opening-night party. Impressed by my moves, Wayne says I am like a “master-level chess player.” I bring him to the party (and Wayne repays the favor by inviting me to take in the Yankees in Lorne Michaels’s box seats when neither he nor Jimmy Fallon can use the tickets).
“Oh my God, there’s Sorkin—I’m going to try to talk to him,” I tell Wayne as we mingle after I nab a photo with Justin Timberlake, who says, “You’re with the Post? You guys write shit about me like every day.”
I literally dodge and weave Sorkin’s assistant, and reach out to shake his hand.
“Oh, I kind of screwed that up,” I say, laughing.
“Should we do it again?” Sorkin asks.
“Well, we could do the Bill Clinton double handshake,” I say, imitating that. “Or the really creepy handshake.”
Then I wiggle my finger into his palm. And hand him my card.
I get an email about an hour later—from Sorkin. I’m still at the party, and I show it to Wayne, my mouth open.
“Mandy, I’m really sorry I couldn’t answer your questions tonight,” he writes. “I hope you had a good time at the movie and the party and I hope I get to see you soon.”
I also meet Lloyd Grove, who had been for a long time the Daily News’s answer to Richard Johnson. I ask him if he’s interested in seeing the script for The Social Network, which one of the Winklevoss twins sent me. “Definitely,” he says.
A few days after that, Wayne is again my plus-one at a party for the release of a Bill Hicks documentary. We are sitting in the audience still, watching folks head out of the Paley Center, when he says, “I think that’s Keith Olbermann.”
“Hey, Keith!” I yell, and Olbermann turns around.
The three of us spend the next hour geeking out over Bill Hicks’s legacy and old Bob and Ray audio recordings. After a while, Keith offers to walk me to the subway, where he kisses me goodbye. I get a complimentary email from him with photos we took together and a friendly warning that he followed me on Twitter.
In the meantime, Lloyd asks me out, and he tells me all about interviewing Sorkin, which led to raised voices and tensions. I email Sorkin, feeling like I’m the cleverest person on the planet, saying, “I hear there was yelling? Sounds exciting . . .”
Sorkin replies, “Ah Mandy, Mandy, Mandy—if we were on a date and off the record, I would tell you all about it, but since we’re neither, all I can say . . . ‘What yelling?’ ”
“But I’m like the queen of off the record,” I write back.
“And I’m the king of getting my ass kicked by Page Six,” he replies.
With all this potential for self-created drama, I have found my new addiction.
So instead of figuring out how I can, you know, be a better person, I instead take to reading Robert Greene books like The 48 Laws of Power and The Art of Seduction, which recommend greasy soul-dead tactics like creating an aura of desirability through love triangles, instilling a “shared feeling of guilt and complicity,” and trying to stir up regression by dabbing milk on your breasts—just in case a guy has a mommy complex.
I never get around to the milk part.
Essentially, I may be sober, but I’m still rotten on the inside: completely disingenuous in my interactions with men whom I want to please, trying to play some heartless seductress—because it feels like a role that is safe and powerful and can’t ever be broken.
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 mo
ments, 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 top. “In fact, in the writers’ room, when talking about this story, we call the character ‘Bad Mandy’ (as opposed to real Mandy) because I haven’t named her yet. I thought it was worth reemphasizing that.”
Of course, I was thrilled. Normally I am very stingy with giving away ideas. As a well-seasoned idea vulture myself, I know exactly how this trick works. Next time that old friend who is now a TV writer calls you up just to “shoot the shit and hear some of your crazy stories,” tell them absolutely, and you in return would love points. See how that goes down. But this was different. This was Aaron Sorkin.
But when I finally watch the fourth episode of The Newsroom, called “I’ll Try to Fix You,” and Will McAvoy (played by Jeff Daniels) meets gossip columnist Nina Howard (played by Hope Davis), and she says, “You just passed up a sure thing,” oh my God, I felt like such a fool. (Later, Sorkin emails, reiterating again the character was not me, but the resonance of feeling like I was throwing myself at him—just like Nina—burns in my brain.)
What hurt the most is realizing that maybe it is supposed to be “the opposite” of me—in reality, there was a close-to-the-bone nailing of all my worst qualities at this time in my life. The sexual forthrightness. The heavy flirtation geared toward a very specific brand of money, fame, power, and intellect.
Meanwhile, in dating Olbermann, there is—fortunately—no Bad Mandy character creation.
But the dates with him are equally, if not even more, unlike anything I’ve ever experienced. All positive—just, you know, it’s Keith fucking Olbermann.
When I bitch about fighting with one of my bosses at the Post, he laughs and says it’s like looking at a reflection in the mirror in terms of the burning-bridges tendency. When we go back to his apartment, I get a small glimpse of his truly amazing baseball memorabilia collection, with an original piece of a now-torn-down baseball field set up right inside his apartment. He even shows me the coolest thing of all, and lets me hold Babe Ruth’s bat for a moment in my arms. His place looks kind of like Will McAvoy’s stunning fictional apartment on The Newsroom, with flabbergasting views of Central Park, eight bridges, Coney Island, and both Yankee Stadium and Citi Field.
At one point, we head outside on to his balcony, where he tells me he likes my height, which is refreshing.
“You’re a good kisser,” he tells me.
“Thank you,” I say.
After a beat, he asks, “What about me?”
“Oh, definitely,” I say.
I don’t relate that detail right now to make fun of him—but to show that whatever you think of celebrities whom you regard as being nothing but celluloid mannequins, they are in fact real human beings. We all want to know if the feeling is mutual.
Less surreal—and more expected—is Olbermann’s inevitable expression of distaste for me. Not me personally, of course, but just why he unfollowed me on Twitter.
“I’m not prudish,” he says, “but the tweets lately have really pushed against my ‘line’ for good/bad taste.”
Yeah—I get that a lot.
In fact, I think my life pushes those same limits.
Indeed, my correspondence during this time is enough to blind any man, woman, or child. Here’s an incredibly painful little sampling:
• “I’m
a terrific person to date. My qualifications include: appropriate quotient of Madonna and whore; mastery of positions including reverse cowgirl but with the naïveté and wide-eyed wonderment of first-time cherry loss; power dynamic fun; psychological fucking ability; ego blow job at the ready; actual blow job at the ready; anal; and natch, cooking.”
• “Is it all right that it makes me wet just to write you? I hope that’s okay . . .”
• “Still thinking about how you played my body like an instrument, making me writhe like a demon possessed by heaven, making me gasp out for more, more, more.”
I think that’s enough to make you sufficiently lose your lunch without me needing to provide any further examples of more, more, more.
But oh man, such good stories, right? Know what’s great to cuddle with at night? Stories.
And, in case it’s not clear, for the record, whatever flaws any of these guys might have, the only jerk in this entire situation is me.
All three are hugely talented and impressive men—who were essentially in the crosshairs of a (while highly delightful at times) newly sober hyper-opportunist who had substituted her old addictions with a new one: trying to hitch herself to a powerful man in order to avoid the hard work of looking at herself. (And for context, to be clear—I dated Lloyd very seriously for almost a year and saw Sorkin multiple times over the course of several years. Olbermann and I only went on a few dates because my relationship with Lloyd took off, but it was hardly comparable. Still, the fact that I actively tried to pit each guy against the other still makes me cringe.)
Essentially, I might have been sober, but I was doing everything I could to avoid feeling some of the pain that was coming up for me.
After this saga of romancing the A-lister trifecta ends, I throw away all my Machiavelli-inspired Robert Greene books, and resolve to be more authentic overall.
I am pleased to discover in the process that I have developed one firm boundary I never have before: my sobriety.
Near the end of the year, I meet a very charming man in his thirties: Jackson, a wealthy artist who is also sober and pretty much seems too good to be true. He can’t provide any media introductions. He can’t get me a killer agent. And I lay off all the shape-shifty “please project onto me any fantasy of what kind of woman you want me to be so I never have to actually figure out who I am” rhetoric that I had been shoveling prior.