Connotative/Denotative: LIVING the DREAM, Webisode 2

Years ago, when I was a first-year associate at Skadden, I was at a bar, drinking, hanging out with a bunch of super-intense associates, when a cute girl smiled at me. I smiled back. Moments later, I was talking and flirting with her. She was young, cute and drunk. It was perfect—until I responded to some inane question with the following question “Do you mean that in the connotative or denotative sense?” The sexual energy vanished instantaneously. Her smile turned to confusion, then contempt. Did you really just say that? Are you that big of a loser? Moments later, she was gone. Just like that.

I’m not George Clooney, but I’m not a total dork either. So why did I say something so stupid to a beautiful, buzzed woman?  Because I was a first-year associate at a big firm. Because I was inundated with annoying smart-people banter and witticisms.  Because I was surrounded by insecure Law Review geeks who were constantly trying to sound smarter than everyone else. Without knowing it, I’d lost all context for what normal people find funny–or even acceptable. I’d been trapped in a bunker with over-achieving M&A geeks for months at a time. What’s funny at 2 a.m. in the middle of a hostile tender offer ain’t necessarily so interesting at Bungalow 8 on a Saturday night.

So this episode is a simple homage to my junior-lawyer-pseudo-intellectual-self-consciously-arrogant lameness–and a cautionary tale to all young, single lawyers on the prowl. Never, ever use the words “connotative” or “denotative” when talking to drunk, sexy women.


    Words to live by…

  • Nick Santora


    As you know, I’m a Columbia grad and a Sullivan & Cromwell alum … and I still don’t understand the connotative/denotative joke … that’s how dumb I am!  What I do know is that your episodes of LTD (see, I created that user-friendly abbreviation … patent pending!) are hysterical.  Keep up the great work.



  • Big Law Alum

    Awesome!  So funny…. Thanks for creating all this, keep it coming.

  • Crippled Monkey

    I loved the conference room scene.  Nothing is more honest about law firm life than butt-sucking associates laughing at a Partner’s lame joke.

  • Al Dickman

    These people just follow the partner like lemmings.  They don’t know jack squat about anything but if the partner laughs, they do too.  Typical asswipes.

  • anon

    So denotative use is when you intend the literal meaning, and connotative use is when you intend a more figurative meaning.
    I get that but I don’t see why the joke is funny. What is the literal meaning of lopsided as applied to a deal?

  • Brett

    Good Lord, anon.  That’s the point.  It’s not funny unless you’re stuck in a room of Type-A overachievers, kissing the bosses ass.  The lack of funny is what makes it funny.  Like when you tell a lame law joke: the lawyers laugh and everyone looks at you like you’re an idiot.  Of course, if your comment was meant in the non-funny funny sense, I apologize.  Sarcasm doesn’t go over well in print.