Jessica Simpson, With Sympathy


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.

Law Firm 10 may lack the dazzling, magnetic charisma of a girl from the hottest sorority in school, but she (arguably) makes up for that with her wit, humor, and low-maintenance-ness. Read more from Law Firm 10.

22 Comments

  1. Guano Dubango

    August 3, 2009 at 3:16 am

    I have been looking for a long time for a female lawyer who is (i) very attractive, (ii) smart/talented, (iii) personable and (iv) willing to bear me children.  I have been told many times this person does not exist.  Now I read of such a person?  Can this person be for real?  Is this woman actually as attractive as Jessica Simpson?  Can she sing nicely, or at least be smart at work?  How personable is this LF10? and lastly, she seems to be interested in bearing children, so that is good.  If she is truley willing to be my wife, she can contact me, Guano Dubango, c/o this website.  Thank you.

  2. BL1Y

    August 3, 2009 at 4:46 am

    Poor, poor LF10.  You were so close to making progress when you starting talking about how you come across as being desperate.  Yes, that will drive men away.  But then you have to go and play the “men are intimidated by my money” card and ruin it.  This is one of the lamest excuses in the book.  Men are NOT intimidated by successful women.  We want successful women.  We want women who make a lot of money.  Stop using your job as a cover for your shitty personality.

  3. Guano Dubango

    August 3, 2009 at 5:04 am

    BL1Y is right.  I also want a woman who make a lot of money.  But is this LF10 have a lousy personality?  I do not like that.  Unless she is very nice to me, it does not matter, and if she is not deferential, I do not want her.  In my country, it is important to have woman who serve her man’s family well.  If this woman is unwilling to do so, I hereby rescind my offer of marriage to this woman.

  4. BL1Y

    August 3, 2009 at 6:42 am

    $10 says Alma responds as though Guano is serious.

  5. Lawyer Bob

    August 3, 2009 at 7:18 am

    We can’t take that bet, BL1Y. It’s a sure loser. Alma is too predictable.

  6. SDL20

    August 3, 2009 at 7:45 am

    this new guano character is hilarious

  7. Er, no.

    August 3, 2009 at 7:51 am

    Once again, LF10’s ego leaves no room for any guy in the room.  At least not one with any self worth.  And isn’t this the same woman who said dating was her way of playing “Make me a millionaire stay at home mom?” And guys are supposedly intimidated by her making more than they do?  Er, no – a lot of us just have no interest in working our asses off to support you in a six figure lifestyle while you play mommy.

  8. Craig

    August 3, 2009 at 8:20 am

    I agree that this Guano guy is pretty funny.

  9. Joes

    August 3, 2009 at 9:10 am

    A hot dog contest very funny!!

  10. Alma Federer

    August 3, 2009 at 10:02 am

    Why are you men so down on women who are successful?  Both me and LF10 have to put up with the likes of men who only are interested in us for our bodies (and our bank accounts).  I personally am not interested in this Guano, nor do I understand the rituals associated with his home country, though it sounds like it’s somewhere in Asia or Africa, neither of which places I care to go to.  However, he has some redeeming qualities.  He will be true to his mate and will not be dipping his wick elsewhere once he finds a mate.  Again, I do not personally care for him, but I admire his sexual loyalty.

  11. Alma Federer

    August 3, 2009 at 10:13 am

    One addendum.  When I was in law school, I was considered better looking than either of the Simpson sisters.  Men referred to me as “Charleze from 30” (meaning from 30 feet away).  Once you came closer, you could tell that I was not, in fact, Charleze Thereon, but that is a GREAT compliment to both me and her, since I have a law degree.

  12. BL1Y

    August 3, 2009 at 11:03 am

    Did Alma really just admit to being a Monet?

  13. Guano Dubango

    August 3, 2009 at 11:19 am

    I came to the USA in search of a prize bride, Alma, and I will not settle for less.  In my country, Ghana, we have plenty of women, but none who are (i) accomplished (ii) very attractive and (iii) who will be true to me and bear healthy children.  I have worked very hard, have lived in USA for 10 years and received American law degree (LLM) and expect to return to my home country with a bride and children once I have banked over $1M USD.  From there, we can retire to a life of leisure in the hill country with multiple servants and hot running water.  If there are smart, eligible women other than LF10, please send a note to the website in c/o Guano Dubango.  I am sorry, Alma, I do like Charleze Thereon, but will only marry someone who loves me and will be true to me.  You may be a bit too forward for my tastes, also, and I do not want for you to stray once we return to the hill country.

  14. Anon Female

    August 4, 2009 at 10:03 am

    great piece LF10!

  15. LawProf

    August 5, 2009 at 6:41 am

    So sad. You are obviously smart, LF10, but you have no insight. Of course you come off as desperate, and desperately shallow. In all your columns you talk incessantly about being married, having kids, being wealthy, getting a big diamond, but that’s all you talk about. You talk about men solely as suppliers of the good life for you. What about love? What about being in a relationship? What about personal qualities other looks and wealth? What decent, caring guy would possibly want to spend time with a women who sees them as nothing but a cash machine with testicles? I see law students like you all the time, and it’s very sad. You are doomed to a life of misery, unless you figure out what really matters. You’ve got the brains to do it, but can you?

  16. Be Sharp.

    August 6, 2009 at 3:29 pm

    I love you, LF10. You’re too good at self-deprecation to be half the loser you claim you are. Thanks for the laughs.

  17. OSCAR The Grouch

    August 7, 2009 at 12:42 pm

    I love the smell of desperation first thing in the morning.

  18. Dougie

    August 8, 2009 at 10:17 pm

    lot’s of good laughs – you sound pretty cool.

  19. robert smith

    August 11, 2009 at 10:07 am

    move to LA: we’re nicer here and like babies even if those cold people in Chicago don’t.

  20. The truth...

    September 2, 2009 at 7:56 am

    You don’t love yourself. You don’t even know the meaning of the word. Until that happens you will not realize that dreamed relationship. You don’t see men as other human beings who have needs and wants. In a way, you are the counterpart to guys who are ‘players’ they chase tail endlessly but its never what they want. They don’t see women as human beings. Living this shallow life will not produce meaning.

  21. female lawyer

    September 13, 2009 at 6:34 pm

    interesting post.  wow, these commenters are so harsh… makes them look pathetic!  like the one “law prof” who said you’re “doomed” to a miserable life.  wtf?  what kind of a person tells someone they are “doomed” to any kind of life.  you’re young, smart and make good money.  i don’t think that “dooms” you to any kind of life.  Actually sounds like a great starting off point for an AWESOME life.  and the BL1Y dude… i know firsthand that there are a lot of males who are intimidated by highly-paid women.  guys can be so insecure.  its sad.  anyway, that BL1Y guy sounds like a loser.

  22. James Liu

    September 26, 2009 at 7:58 pm

    Really, fitness & food options that exist in LA that don’t exist in Chicago? You have to be kidding me, right? I don’t work at a law firm, but I did work in the loop, and every day on my way to work I was solicited by overly eager LA Fitness employees wanting to sell me a membership.
    And granted, there isn’t a Chinese-Buddhist vegetarian restaurant in Chicago, but if you ignore the distractions there are plenty of ways to eat well and healthily in Chicago. My first hint is Pastoral, 53 E Lake. Droolworthy healthy options. You have to earn biglaw money to eat there every day though.

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