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.
After I’ve been dating Jackson for a few months, we spend an evening watching Saturday Night Live together at his beautiful Central Park West high-rise. It feels
