
Coming out of college I worked for a year in admissions, then took a job as a graphic artist in marketing with an investment company. That move back to Chicago broke off the relationship with the woman with whom I’d fallen in love in college. But she was keen to marry far sooner anyway. I wasn’t ready for that.
In fact I sat in the company cafeteria explaining that breakup to a woman who was twenty-seven years old at the time. Her bright red hair and flashy red lipstick gave her an urban diffidence that a twenty-two year old like me did not know how to handle. Then she regaled me with a tale about how she liked to crawl under the breakfast table and give her man a real treat to start the day. That was when I began to realize there was an entirely new way of looking at the world. Older women seemed to know about it.
She told me without apology that I was far too young to be engaged to that college girlfriend, especially one that demanded no less than a carat diamond ring for the engagement. “You’re better off without her,” my female advisor admonished.
Meetups
The following year when I was turning twenty-three years old, I met a woman who was thirty-three. We talked at a bar and it turned out the she knew a close friend of mine. That kept the conversation going and I pushed for a date.
It wasn’t until a week later that I learned her real age. At first glance, that gap of ten years seemed significant. But the seasons were turning from spring to summer and everything seemed possible. So we started dating. And we had fun.
I was just in the process of moving from my parents home to a coach house apartment where my former track coach had lived. When the place opened up I was eager to move out and start on a new track in adult life. That little coach house became a party center for my extended group of friends. Some of them just came to drink, smoke pot and carouse. Others wound up screwing on my couch. It was all part of twenty-something life.
Wardrobe fixes

Meanwhile that older woman and I were getting together more often. Yet I turned up for a date one night and she looked me up and down and said, “You think I’m going out with you in that?” I was wearing the classic runner getup of the day. A County Seat plaid country shirt with pearlescent buttons, a set of scruffy corduroys and some well-worn running shoes.
“Here’s what you need to do,” she advised me. “Go to Marshalls. Buy yourself a nice set of khakis and a blue pinstripe shirt. And some real goddamn shoes. Then come back another night.”
That might have seemed harsh, but even at the time, I did not blame her. Runners were a sorry-looking bunch as a rule in the 1980s. Most of us were so thin our cheeks resembled hollowed out cereal bowls. And those old running shoes we wore around? We saw them as running chic but they were instead ugly as hell, awkward and heinous.
Admittedly, I’d already been taught a few fashion no-nos by that college girlfriend. So I realized there was probably plenty still to learn, especially from a far more experienced older woman.
So I went shopping.
The running thing
Up until that point in time my life was defined by experiences in running. All my social life centered around running and runners. I assumed that dedication to the sport might somehow, someday impress women. So I invited her to watch my best friend and I work out.
To her credit, that woman parked herself on the aluminum high school bleachers at the track one night while my best friend and I ran a set of twelve sub-65 second 400 intervals. I’d glance up now and then wondering what she thought. After our training session her first observation told me how she viewed the world. “I liked that both of your legs were in perfect sync. That looked really cool.”
She didn’t look at this running thing as some measure of character as I did. She viewed it as one more facet of this world to be analyzed for its value based on perspectives other than those I wished her to see. It is the best thing in the world for a young man to learn that a woman has a mind of her own, and the right to use it.
Working it out
That type of lesson came around more than once during our time together. I showed up unannounced at her place one day and found her immersed in the restoration of an antique chair. It looked only like an old chair to me, but she recognized its unique qualities. In fact she worked as a home remodeler, fixing up fancy apartments using amazing finds like that in the Gold Coast neighborhood of Chicago. She made close to $100K working only six months of the year.
That first summer I knew her, she decided to take a work break to drive around the country in the green Volkswagen van that she owned. She invited me to come along but the concept of ditching work to drive around the country and get high in a Volkswagen was foreign to me at that moment.
Her van only broke down once during her trip. It surprised me that she called from a pay phone sounding a little worried but not scared. No one’s perfect, I thought. But she seemed so far away it was hard to imagine her ever coming back.
Home and away
When she did return we used the rest of the summer to get high, and fairly often. That woman was a pot connoisseur with a collection of pipes and bowls and bongs as well as connections to import weed from far-flung places.
I didn’t mind getting high now and then, but it was also a year when I was starting to make big progress on the running circuit. My 10K time dropped closer to 32:00 with each race. With an efficient cardiovascular system like that, it took only a few puffs on a joint or a deep draft on a bong to render me half a world away from home.
Our worlds seemed distant in other ways as well. She didn’t know much about rock music, which surprised me on many fronts. Yet she somehow latched onto the song Tale of Brave Ulysses by the group Cream and especially liked these lyrics:
And you see a girl’s brown body
Dancing through the turquoise
And her footprints make you follow
Where the sky loves the sea
And when your fingers find her
She drowns you in her body
Carving deep blue ripples
In the tissues of your mind
It’s a pretty intense song I suppose, especially when you’re high as a fucking kite. That “carving deep blue ripples in the tissues of your mind” lyric when breathed through headphones heightened by waves of hardcore THC ripping through your brain is nothing to sneeze at. So we got high, had sex now and then and tried to figure out if we were long-term compatible.
Then one night we ate ice cream on a park bench after smoking a bowl of pot. I was so out of it there was no guarantee I could even walk home. I looked across the parking lot and it felt like the world I knew was a thousand miles away. Some people smoke pot to get in touch with themselves. For me, it felt like the exact opposite.
At 7 Eleven
So it became clear that she lived in an alternate universe from mine. There were hints that I never really scratched the surface of that world. Bumping into her chest with my elbow one afternoon at the 7-Eleven, she reacted not with a jolt, but with a smile.
The attraction was there alright, but so were the reversely magnetic effects of age, experience and habits. I never heard from her again after we broke off the relationship, for some reason I have no photos of her at all.
It was the first time I truly realized that one world can run into another and never truly meld together.