The year 2001 will forever be a stain on the trajectory of human history thanks to the 9/11 terrorist attacks, but in spite of those terrible events, that year will go down as one of the best of my life.
Having freed myself from the noose of a terrible relationship, I had no intention of entering into anything resembling a serious relationship (I believe my exact words were “never again”). I went out and moved on, preferring instead to think of dates as friends hanging out long before “Netflix and chill” became a thing. Highlife provided ample opportunities to meet new and interesting people, but I was having too much fun to settle down.
The New Year also brought a new challenge. I had decided to attempt a marathon. I had never run anything more than a half marathon, and I had no clue what training for a marathon would involve, but I was determined to give it my best shot. After reading a book about completing the distance, I began to train in earnest for the next Chicago Marathon in October, but I often found my social schedule at odds with my ever-longer runs.
In late April, I joined several of my friends for a Highlife-sponsored dinner at an Irish restaurant west of Chicago. We had one of those long, rectangular communal tables that sat about 20 people in a small, roped-off section of the restaurant. The host greeted us at the entrance and we took our seats at one end of the table as the rest of the guests slowly filtered in. The waitress took our drink orders and I fell into an engaging conversation with two friends and a couple of other people I had never met before, a typical hyper-social event for Highlife.
The seats filled up rapidly and our end of the table became embroiled in a raucous discussion about the Cubs vs. the Sox when a young woman with the most beautiful smile I had ever seen joined our group. I watched as she waved to a few people at the table and walked to the opposite end to have a seat. The distance between us felt like a mile in that confined space, too far to talk or shout a conversation. I wanted to meet the woman who possessed that smile, but we were both pinned at our respective ends of the table by other friends and lively discussions and the night slipped away before I had the chance to introduce myself.
Fortunately, I did finally meet her and introduce myself. It happened over several subsequent Highlife events that both of us attended where I eventually learned her name was Tiffany. Not only was she an incredibly beautiful woman with a captivating smile, but she was down-to-earth and damn cool, too. She liked to do many of the things that I enjoyed doing, which explained why I kept seeing her at the Highlife events I attended. I’d never met a woman as interesting and fun to talk to her as she was. We developed a rapport and started chatting outside of the Highlife diaspora.
Eventually, I asked her out on a date to a Train concert in mid-May. I did it through email because I was at work when I finally got the nerve to ask her out. Those minutes between the moment I hit send until I received a response from her felt like endless, tortuous hours. When her response popped up in my inbox, I nervously clicked on her name to see that she said yes.
Relieved, I could sense the start of something wonderful. That single email started a chain of events that made my year, my life even, and it remains one of the most fortuitous turning points in a life full of them. On that first date, in spite of the loud music, we talked most of the time, leaning into each other so that we could talk over the music. Each time I got close to her, I could feel the electricity between us, and the more I got to know her, the more I liked her.
We didn’t stop there. Our next date involved tandem skydiving, which was second only to her in terms of sheer thrill. We spent that entire summer together doing everything, anything, and nothing. We drank from the fountain of those long summer days in Chicago like draining a beer in the bleacher seats at Wrigley Field. We capped off that magnificent summer with a trip to Italy as part of a Highlife tour group. By then, I knew that I loved her. I couldn’t imagine my life without her, and I seriously considered proposing to her on our Italian vacation, but I decided to hold off to make sure she could handle being with me for seven days in sometimes cramped and unfamiliar conditions. If she could survive that, I knew she could survive being married to me.
Luckily, the wonderful tour of Italy confirmed what I knew in my deepest heart to be true. We explored all of the familiar landmarks in Rome, Florence, and Venice, and finished our trip near the southern Alps in Lake Maggiore with a memorable night in a quaint, Italian resort town. Most importantly, all of that time together in tiny hotel rooms with inconveniently-sized bathrooms that seemed like an afterthought and on the confined tour bus did not send Tiffany screaming for the exit.
Instead, we returned to the U.S. more in love than ever just in time to experience my personal low point of that year. In early Oct, I ran the Chicago marathon barely a week removed from our Italian adventure. Being my first marathon, I didn’t know what unprepared felt like, so I toed the start line that day in the throes of blissful ignorance as Tiffany cheered me on. The large crowd propelled me through the first ten miles with a smile on my face, but as the seemingly-endless miles wore on and the crowd thinned, my “preparation” came back to haunt me in a bad way. By mile 18, I shuffled along like a drunk trying to find his car in a blizzard. I stopped and walked a bit to make the pain stop, but it didn’t help. Forced to choose between quitting and finishing the race, I shuffled-stepped my way to the agonizing finish line near Buckingham Fountain.
After four hours and ten minutes, I trudged across the finish line a broken man. When I met Tiffany near the fountain, I collapsed on the ground beneath my feet and cursed my penchant for crazy ideas. She sat patiently near me as I wallowed in disappointment and belittled my own poor effort. I told her I would never run another marathon again. It would take me eight years to eat those words.
That small fracture in the most wonderful year quickly faded into my memory after I recovered. On the date that marked six months since that first date, I took Tiffany on a dinner cruise on Lake Michigan aboard The Odyssey cruise ship that often sailed along the shoreline by Chicago. I wore a suit, and she wore a gray formal dress that accentuated those feminine curves that left me googly-eyed. She looked positively stunning making her smile all the brighter. After dinner we ventured downstairs to another part of the ship where I bent down on one knee and asked her to marry me. She said yes, very quietly at first, but then, she excitedly repeated her answer. I had never been happier in my life.