As the year moved on, the city got a little less colder, and the days grew a little longer. Slowly, I saw signs of life coming to Chicago. Layers were being shed, physically and emotionally. Down jackets became raincoats and snow shovels turned into umbrellas, and boots were traded for platform heels, peep-toed pumps and pedicures.

I still hadn’t swam in months, but I began running. And I ached, even though I lost 15 pounds and my waist narrowed and I shaved 90 seconds off my 5K time from college. My clothes were loose, too.

Chicago held a strange fascination for me, especially the Drake Hotel. On a slow day in the office, I walked all the way to the Drake on my lunch break. I had fantasized about it after watching a Julia Roberts movie set in Chicago, in which the female lead cha...

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