Call me crazy (it wouldn’t be the first time), but I actually feel really, really badly for Jessica Simpson. Mainly because she and I have a hell of a lot in common.
“How Jess Drove Tony Away,” screamed the headline of one of the US Weekly magazines I use as brain-numbing cream for my El rides to and from BigLaw. That pretty much sums up the last six years of my life. Simply replace “Jess” with “LF10,” and substitute “Tony” with “Josh, Chris, Ryan, Rob, Rory, Pete, Darrow, Shawn or Dave.” I’m probably forgetting a few. And many of them were just as douche-y as John Mayer.
Jess and I are clearly plagued by the same chief problem: We’re both attractive and fairly successful, yet somehow we both come off to the men in our lives as desperate. I probably should’ve invested my It’s Just Lunch money into a study on what it is about me that screams “Marry me and let me bear your children” in such a suffocating way. And then into a 12-step program for how to hide that vibe from potential suitors. I’ve followed the rules of He’s Just Not That Into You since the beginning. I never, ever call a man—but the results are dismal and Simpson-like. It’s time for something else. But what?
On an even more personal note, Jess and I share something else—namely, a younger, thinner, more-attractive sister whose own relationships and personal life have evolved embarrassingly beyond our own. While Jess turned 29 last month all by her lonesome, out with a few girlfriends and maybe that new Katherine Heigl movie that looks so humorless and trite that I want to set myself on fire in protest, her younger sister was cleaning her dazzling wedding rings and bouncing her little boy on her knee… Er, strike that—Ashlee was probably sipping a Bellini while watching her assistant clean the wedding rings and the nanny play with the baby. Even more jealous-inducing, in my opinion.
By way of comparison, my grandfather’s favorite topic at family dinners (after two martinis chased with a glass of Chianti) is to say that everyone’s expecting my baby sister to get married first. Then he quips something consolatory about what a good “career gal” I am. Sweet. I wonder if creepy Joe Simpson’s father felt the same way about his granddaughters.
Lest we forget the now-infamous weight fluctuation issue. I’ll admit that it makes less sense in Jess’s case. She doesn’t sit on a desk chair for 10 hours a day, 7 days a week—not to mention has access to some amazing trainers and Los Angeles food options that do not exist in Chicago, let alone in the three-mile feeding radius around my office. But I can relate all too well. Like Jess, my ability to refrain from margaritas and vats of guacamole is directly related to motivation, which rises and falls depending on stress level of the case I’m working on or whether there is anyone in my life in front of whom I need to look good—or, more often, an ex I’m dying to make jealous.
Finally, I’d be remiss if I didn’t mention that pesky issue of emasculation. Who could forget Jess’s disaster of a first marriage that ended in ruin when her own fame eclipsed her husband’s? I can relate. I earn more than two-thirds of non-lawyer males in Chicago, and I blame my salary for the fact that I’ve hardly ever gotten past “Hello” with any single advertising, accounting, or marketing guys.
In any event, Jess, I feel for you. Maybe next time you’re in Chicago performing at a hot dog contest, we can meet at The Twisted Lizard for some steak quesadillas and Patrón shots as we figure out how to disguise—or better yet, shed—our desperation together.