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.