Lettermanning (The Maybe You're the Problem Heuristic)

“ Maybe you’re the problem, do you think?”

When Lauren Conrad, star of MTV’s The Hills, appeared on the Late Show with David Letterman in October 2008, her interview took an unexpected turn. The first minute was standard talk-show banter for a twenty-two-year-old star of a successful reality series: the amount of drama in her life. Less than a minute later, Conrad asked Letterman if he was calling her an idiot.

She started off the interview by discussing her ongoing feud with her by-then-former roommate Heidi Montag and Heidi’s boyfriend Spencer Pratt. In case you’re not familiar, here is the backstory: Lauren and Heidi’s friendship ended when they came to blows at a birthday party after Lauren accused Heidi and Spencer of starting rumors that she had made a sex tape. In addition, Lauren developed friendships with Stephanie (Spencer’s sister) and Holly (Heidi’s sister), complicating the social and family encounters of everyone involved. Lauren tried without success to strengthen the relationship between her roommates, Audrina and Lo. This strained Lauren’s friendship with Audrina, who reestablished her friendship with Heidi. Brody Jenner was also in the mix, dating Lauren, questioning her date with a Teen Vogue model, dating someone else himself, arguing with Spencer about his friendship with Lauren, getting accused of starting the rumors about Lauren’s sex tape, etc.

All of that drama happening in Conrad’s life is what David Letterman was referring to when he interjected, “That raises the question, maybe you’re the problem, do you think?” That quip sent an interview that was supposed to be a puffy, promotional chat into an uncomfortable tailspin.

Letterman immediately realized that he had taken the conversation into much deeper, more serious territory than either of them could have anticipated. He tried to soften the blow in a self-deprecating way, adding that he had done the same thing, for years refusing to close the learning loop by assuming everybody around him was an idiot.

“Let me give you an example from my own life. . . . For a long time . . . I thought, ‘Geez, people are idiots.’ Then it occurred to me, ‘Is it possible that everybody’s an idiot? Maybe I’m the idiot,’ and it turns out I am.”

Conrad clearly didn’t want to hear it, replying, “Does that make me an idiot, then?” Websites devoted to reality TV, gossip, media, and popular culture immortalized the moment, and that’s how they saw it: Letterman “basically calls Conrad an idiot” (Gawker.com), “ripped into” Conrad (Trendhunter.com), “makes fun of Lauren Conrad” (Starpulse.com).

Letterman’s comment was actually quite perceptive. His mistake was offering up the insight in an inappropriate forum to someone who hadn’t agreed to that kind of truthseeking exchange.

Conrad certainly had a lot of drama in her life: enough that MTV created two successive shows to document it. But, like most people do, she characterized the drama as a series of things happening to her. In other words, the drama was outside her control (luck). Letterman suggested some of it could be fielded into the skill bucket, a suggestion that might have been helpful to Conrad in the future if she had been receptive to it. Not surprisingly, she wasn’t.

Letterman had offered the helpful alternative hypothesis, unexpectedly, on a late-night talk show where the norm is fluff and PR. Perhaps Letterman’s approach would have been more appropriate in an Oprah Winfrey–style prime-time interview. Or on one of those reality therapy shows where reality stars agree to such an exchange. As it was, he violated the assumed social contract by challenging Conrad to bet on her outcome fielding when she hadn’t agreed to truthseek with him.

That exchange was similar to my interaction at the poker tournament with the six-seven of diamonds guy. I thought he was asking for my advice, so I responded by asking for more information to get an idea of whether he accurately fielded his losing outcome as luck. He was expecting me to adhere to the norm of being a sympathetic ear for a hard-luck story. When I attempted to delve into the details, I violated this implied contract. I Lettermanned him.

Such interactions are reminders that not all situations are appropriate for truthseeking, nor are all people interested in the pursuit. That being said, any of us who wants to get better at thinking in bets would benefit from having more David Lettermans in our lives. As the “original” Letterman learned from the awkward exchange with Lauren Conrad, Lettermanning needs agreement by both parties to be effective.