I moved home after college and took Paula’s old job tending bar at the seafood restaurant. The bar’s patrons despised me for two reasons: one, I wasn’t Paula (she and her tight T-shirt collection had gotten engaged to a bald lawyer and moved to Albany); two, I constantly read fat novels behind the bar and would act put out whenever any of the fishermen asked me to refill their empty draft glasses or fetch more pretzels.

I was patiently waiting for my life to start. My parents’ disappointed faces, which I saw each night at the dinner table over plates of spaghetti, reminded me of the fact that it hadn’t. My fellow classmates all seemed to magically have predetermined post-college destinations laid out for them, as if they’d received maps and detailed instructions via mail explaining exactly what to do next. One classmate reported to Lehman Brothers less than 48 hours after graduation where a desk was already waiting for him (he actually showed me a photograph of the desk); another had a job lined up in the mailroom at a famous talent agency; still another had gotten engaged to his high school girlfriend and was planning a spring wedding. Even the pot smokers, who’d rarely left their rooms for four years, had somehow managed to arrange elaborate backpacking trips across Europe that would crescendo with long, smoky stays in Amsterdam hostels. As we said our goodbyes on the Great Lawn or whatever the pretentiously named centerpiece of the campus was known as, I could already feel the distance opening up between us. These people had real-world concerns—rent, neckties, EuroRail passes—and those concerns gave them a maturity and authority that I did not have.

I checked our mailbox every day, to see if my instructions arrived. All I found was the Pennysaver along with the occasional dead spider.

One night at the bar, one of the tipsy fishermen had had enough of my eye-rolls. “I’m merely asking you for a glass of beer, son,” he said, “but you always act like I’ve asked you to go to my house and make an attempt at pleasuring my wife.” The entire bar broke up laughing. The man passed a photo of his wife the length of the bar. She looked like Henry Winkler in a fright wig. I laughed, too, and gave the guy his beer on the house.

Back at home, my parents asleep in their room, I watched the introduction to the Letterman show at a low volume. The show’s opening featured a camera soaring over the same twinkling Manhattan buildings where my classmates now lived and worked. I was sick with envy. I contemplated growing a beard. I’d never grown a beard before and wondered if I had it in me, if my face could pull it off. To help stave off my despair, I made late night phone calls to my classmates, including to a rogue group who had moved not to Manhattan but instead to Chicago. The de facto spokesperson for the Chicago contingent was a gangly girl named Sam. She wore her hair like an Indian squaw. In the campus dining hall during the first weeks of her freshman year, Sam’s feet had gone out from under her while transporting a tray of cafeteria food. The result was a dining hall-silencing accident that stigmatized Sam for the remainder of her college life. As if that wasn’t unfortunate enough, Sam had sprained an ankle during the fall and was forced to use a cane for several weeks afterwards, prompting the cruelest among us to forever refer to her as “Oscar Wilde.”

Because I’d suffered my own embarrassments at the hands of my classmates, I had always felt a vague kinship with Sam. “You should come to Chicago,” Sam said to me over the phone one night. I could hear cars honking in the background as she spoke. “Everyone is here,” she said. I asked who “everyone” was, and she rattled off at least 15 names of people from our class. I didn’t recognize most of the names. “We all live within a three-block radius of one another,” she said. They had even staked out their own local Houlihan’s where they met every Friday night for happy hour.

Sam was living with two other girls from our class—both very pretty—and was working as a real estate agent. “You can stay with us when you arrive,” she said. “Our apartment is huge. You’ll love it.” The idea of rooming with three beautiful women, even if it was only for a few days or a week, made me feel like I could live out a real-life version of the sitcom, Three’s Company. I pictured our landlord looking exactly like Mr. Roper. “Since I work in real estate, I can find an apartment for you,” Sam said. “Or, the alternative is, you can keep on living with your parents and keep on wondering if you can grow a beard.”

I winced, berating myself for sharing this silly piece of information with her. “But I’ve never even been to Chicago,” I said.

“You’ve never been anywhere,” Sam said.

Which was true. Aside from a miserable family camping trip to Cooperstown, my travels had been extremely limited. “You make it all sound easy,” I said.

“It is easy,” she said, putting the mustard on the “is.” “All you need to do is get here.”

After I hung up the phone, I kept hearing those words in my head: All you need to do is get here. It seemed risky and impractical to me, moving 1,500 miles to a city I’d never even visited. The next morning, I went to the mailbox to collect the Pennysaver, and, to my surprise, I found the long overdue instructions—or at least part of the instructions—that I’d been patiently waiting for since graduation. A month earlier, on a whim, I’d mailed off a postcard to the Letterman show requesting tickets to the 10th anniversary special to be held at Radio City Music Hall. There, inside the mailbox, inside a nondescript envelope with a return address that read simply “Rockefeller Center,” were the two tickets I’d asked for.

I stood there in front of the open mailbox, my heart pounding like mad. A light snow began to fall. Our house, which sat about 30 or so yards off the road, suddenly looked small and far away to me. Smoke chugged from the chimney. A hushed silence came out of the surrounding pine trees. A chainsaw started wailing in the distance. I looked down at the pale blue tickets in my hand, and felt, for the first time in months, that maybe things would be all right after all.