How to Deal If You're on a Boring Date

JGI/Jamie Grill

In her new book, Are You A Jackie or a Marilyn? author Pamela Keogh describes the habits, inclinations, and experiences of two of America's biggest female icons (Jacklyn Kennedy Onassis and Marilyn Monroe) in the interest of giving readers a few life lessons. Her publicist got in touch with me the other week to tell me about the book, and after some back and forth, Keogh sent me some thoughts about Jackie and Marilyn's "deal-breakers."

One anecdote from Keogh's list jumped out at me: Boring conversation was a dealbreaker for the former First Lady Jackie — who was ready to yawn when she met Russian Prime Minister Nikita Khrushchev for the first time, at the height of the Cold War. He began spouting off all sorts of facts and figures, meant to illustrate the benefits of Communism … but Jackie quickly shut him down by saying flirtatiously, "Oh, Mr. Chairman, don't bore me with statistics."


How many times have I wanted to say something similar on a date — when a guy has tried to regale me the minutiae of a financial or political or technological job? How many times have I heard such coma-inducing details that I considered faking some kind of seizure or food poisoning to escape from such a discussion?

A lot.

But as I've gotten older, I've realized that being passive-aggressive only makes for an unhappy evening. Instead, I try to tell myself, "Look, you can either sit here being grumpy or find a way to enjoy yourself, and maybe learn something."

Changing the subject, the way Jackie did, is one way to make the experience more pleasant. People aren't mind-readers, particularly not when they are feeling nervous on a date, so they won't necessarily know you're bored or confused by what they're saying until you indicate it in some way — a way that's flirtatious, teasing, light-hearted, or funny.

But what might be easier — what I often do — is to simply try to steer the conversation towards the kind of details that would interest you. I myself am always curious about personal relationships, so I might ask a guy who is going on at length about his job why he got into the line of work he's doing. Was it because one of his parents or someone he admired was in the same field? Or I might inquire about his relationship with his boss, or his colleagues.

Another thing I like to do is to listen more attentively — to concentrate harder, and get a little lesson out of the conversation. I've been out with scientists who've refreshed my basic understanding of physics, and photographers who've given me a better understanding of how cameras work. And though I still don't quite understand the stock market, or the housing crisis, or derivatives, I've realized I really should know more about the economy, so I concentrate more when I'm talking to banker-types these days.

If you want to go so far as to get out a pen and a napkin to take notes on the topic of instruction — or ask your conversation partner to draw you an outline, or some kind of graph — I think you should go for it. It makes the whole thing a little more fun, gets you both a little more invested, and feels pleasantly collaborative.

How do you survive a boring date?

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