The Mighty Queens of Freeville by Amy Dickinson

Author:Amy Dickinson
Language: eng
Format: epub
Publisher: Hachette Books
Published: 2009-02-02T16:00:00+00:00

EIGHT

Playing Hearts

Dating in the Age of Dread

ONE OF MY grander dreams when changing cities was to mix up and revive my dating life. I’d never had much of a dating life, but in Chicago I decided I would become new and improved. I would be better groomed. I’d be more of a “listener.” Maybe I would go to “clubs” and take up “dancing.” I would get contact lenses, wear boots with heels in the wintertime, get a decent haircut, and in general work harder to be attractive. I had never worked at all at being attractive, so working harder didn’t involve a lot of effort, which made it easy to commit to the concept.

I got the haircut and the contacts. I even submitted to a brow and lip wax that left me with red welts in the shape of a Groucho Marx unibrow and mustache. I went home and applied ice to my face, and once the swelling went down, Emily and I decided that I had taken baby steps in the right direction.

Most significantly, Chicago had rolled out the red carpet for me. For a month or so, I was everywhere—on the Today show and CBS Sunday Morning, featured in newspaper advertisements and in a series of radio ads where I talked about my new high-profile job. A week after I’d started writing the “Ask Amy” column, Emily and I took a cab home from the office. The driver looked in the rearview mirror at us and then did a double take. “You’re that advice person! You’re ‘Ask Amy!’” he said.

“But you can call me ‘Ask,’” I said.

Emily and I ran into our apartment, laughing.

“Mom—you’re famous!”

“Jeeze, now I wonder if I should have given him a bigger tip. I mean, I bet Barbara Walters is a big tipper.”

“And Kelly Ripa,” Emily added, helpfully.

The quick flash of local celebrity supplemented my new eyebrows nicely, and for the first time in recent memory, boys started to call.

Despite all of my experience to the contrary, I have always maintained a very optimistic outlook about my romantic prospects—especially during those long dry spells when I haven’t been out much. For me, dating is a lot like going to a professional baseball game—it’s an activity that always seems better in the abstract. I get very excited, for instance, at the prospect of watching the Chicago Cubs play, but once I get to Wrigley Field and have that first hot dog and beer, I’m usually ready to go home. Pretty quickly, the players—like my many blind dates, first dates, future prospects, and near misses—start to blend together, and I wonder what’s on TV.

My first Chicago date seemed promising—as all of my dates do before I have them. This was a person, let’s call him “Leif,” who I rejected (and though other details have been forgotten, I remember this with complete clarity) because of the lettuce.

I was first introduced to Leif just after I started my new job, when he cold-called my office and told me that we knew some people in common.

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