That time I moved to Chicago to live with a guy I'd fallen for over fax.
... and I'd do it again. Life's too short.
In the end we only regret the chances we didn’t take. Lewis Carroll
1n 1994, I met a guy while he was living and working in Chicago and I was in London, working for the Ministry of Sound. When I say ‘met’, these were the days before the internet, so I had struck up a friendship with this man from whom I was licensing some music, while we chatted on the phone. We timed our calls, the six-hour time difference and my work hours needed some coordinating. When we caught the other, we would talk about music, and life outside of work. We would even fax, me running to the other office to grab the curled scroll before anyone could catch sight of our declarations of undying love, and a bit of sexting (sexfaxing?). I got caught out on more than one occasion…
We talked enough that I was asked by the accountant about the length and number of my phone calls to the States. I was legitimately making ‘work calls’, and I always made sure to mention that this label needed a bit of hand-holding. The owner of Ministry of Sound set up a chart of employees with the longest calls, especially the international ones. There was a flip chart set up at the bottom of the stairs to his glass-walled office which was positioned perfectly to watch everyone below. My name was always on there, but I lost out on the top spot to Jim, the head of A&R, who apparently left the phone off the hook after he had been talking to someone in South America, and went back to DJing in the club.
I think I might have legitimately won if they’d ever found out about the call from Cannes. Absolutely hammered, in Cannes for Midem (huge music industry piss-up networking conference, that used to be in January every year: Marché International du Disque et de l’Edition Musicale), my colleague and I returned to our hotel. She was sat watching QVC and I decided, with the time difference in my favour, to call Chicago. Long story short, I fell asleep on the phone. Chicago man tried to hang up but couldn’t clear the line. He called the hotel from another line to try to get them to wake me and hang up. I was dead to the world, and stayed on the phone until the next morning. The bill was so huge, we had to get the hotel manager to fake a dinner charge for six people, despite the hotel having no restaurant. Back in those days, people got away with such hijinx.
During the course of these phone calls, he and I made plans to meet in San Francisco, as we were both going to a music conference there. Somehow the plans extended to me flying on to Chicago, where I would spend more time with him and meet some of my Chicago contacts in person. Miraculously, we met and fell straight into a relationship, without me giving much thought to how this might work. In my single days, I was very much guided by intuition, a gut feeling, or just a sense that life was too short to not try things. So when I flew back to London we kept this relationship going long distance, despite the cost of phone calls and an six-hour time difference, then he flew out here and we hung out in London - he even went with me to get my first, and what ended up being my only, tattoo in a tattoo parlour behind some shops on the Fulham Road. After this back and forth, the next logical step was for me to move to Chicago - well, it seemed logical at the time - so I applied for a six-month visa, quit my job, and in the summer of 1995, moved over three thousand miles away.
I loved it there, living in an apartment in the northern suburb of Evanston, about a block from Lake Michigan. My boyfriend worked for an independent house music label, it’s office based along a bus route that took you through one of the most notorious housing projects in Chicago, Cabrini Green. I couldn’t get my bearings in this new city, being in the States always felt like being dropped into the middle of a movie set, not quite real, like I was looking at it from behind a screen. I was really shocked that those depressing, grey high-rise housing projects were a stone’s throw from the designer boutiques on Michigan Avenue. I heard, while I was there, that Chicago was the most segregated city in the US, but not venturing far from where I had set up home, I remained very much cocooned in white, suburban Illinois, except for those days and nights I was immersed in the Chicago house music scene. The majority of house music producers, artists and DJs were African American, Chicago being the birthplace of yet another music genre after the ‘Great Migration’ seeing Black people bring jazz and blues from the South. Everywhere in the city there were musical influences, head nods to artists and a community feeling around whichever genre featured.
While my boyfriend was at work, I spent my days rollerblading round a loop along the lakeshore, out early in the morning when he left for work. I would skate and see the same people every day, walking bouncy, excited dogs, pushing pushchairs with fussy toddlers, running repeating loops. I got to know the bush along one stretch where the bird would fly out and peck my head - every day I would brace myself, after having been caught the first time, my hand hovering protectively over my head. I would watch as other unsuspecting folk would squeal when it swooped down and mussed their hair with its claws, circling back to its perch.
I had to stop rollerblading for a while once the heatwave of that summer hit - stepping outside was like opening the oven door and wading through a sauna. The humidity was horrific, my skin would be soaked within seconds of leaving the apartment, and the effort of just walking up the street was like nothing I’d ever experienced. I would take myself out every day, simply to stop myself from going insane on my own, and find different coffee shops to glug down a freezing iced coffee, like everyone else, preferring to be in any public place with its a/c chilling the air so deliciously that walking in your skin would erupt in goosebumps. We had a hulking, noisy old a/c unit in the window of our bedroom, which hummed away day and night during that time, but was evidently wired up incorrectly and so it blew the ancient ceramic mains fuses on what seemed like a daily basis.
On the days when I did get out to skate, I would finish my circuit, head back to the apartment, then try to polish my business plan so that I would be able to work. The plan was that I would set myself up licensing music on behalf of artists and producers from Chicago and Detroit back to the UK and Europe, since I already had well-established contacts there, and I knew how to negotiate to their advantage, having been on the other side of the table. I wasn’t technically supposed to work while I was there, and I had enough money to support myself for a while, so I worked towards setting up this business, looking into the logistics of how that might work. True to style, I hadn’t put nearly enough thought into this before I uprooted my life to move thousands of miles, and to another country, but this waiting period gave me time to familiarise myself with my surroundings and attempt to mould myself into this version of me who now ‘lived’ in the States.
It was by no means straightforward. The client I had based my future work on - my boyfriend’s boss, label owner, artist, producer — who was to act as my sponsor while I worked for his label, suddenly became evasive and I couldn’t pin him down to finalise these plans. Eventually, he told me he had changed his mind, he reneged on our agreement, and instead he was going to employ someone in-house to take over his licensing - a young guy who had no experience, a “club kid”.

By this time, I had taken on one other client - another independent artist-producer-DJ with his own label in Detroit. I’m never sure if I should name names, especially as there’s nothing bad about it, so for now he, too, can remain nameless. However, the mainstay of this whole grand plan had been this other label, and with that falling through, the only way I would be able to extend my stay was for my boyfriend and I to get married. We discussed it, it seemed like the only choice, so we started looking into it - my boyfriend wanted to keep it low key, I suggested a trip to Vegas. I think, looking back he knew his family would think a wedding was crazy, but he assumed that they would accept it if we presented it as this contractual conjoining of our lives. We even got as far as looking for a dress for me - not a traditional wedding dress, but something special, something new, something I could wear on the day, albeit a rushed ceremony lining up with the other couples opting for a Cook County judge at City Hall, in lieu of a glamorous celebration with family and friends.
That day that we both knew this wasn’t going to happen was when we got home without that dress, that one symbolic key to the whole process, so we sat down to talk.
“I know your heart isn’t in it, not like this, maybe not with me… I have to go back to London” my face turned away from him, trying not to influence him with the tears that stung my cheeks. I saw him nodding, reflected in the bedroom window.
I felt sick as I ran through all the things I now had to rearrange, to fit back into my life in London. I had rented my flat to a friend, but had to give her notice that I was coming back early. That didn’t go down too well, and she refused to move out. I had to fly home with nowhere to live. But once I had made that decision, I just wanted to be gone.
As we made plans for me to leave, he suggested that he instead move to the UK, the idea keeping the relationship alive and softening the blow of me going home. He worked in the industry too, and we knew he would find work in any number of labels in London, so there was a renewed excitement which made up for the disappointment of my failed adventure.
I left Chicago, thinking on how many times I had made this kind of trip alone, maybe this was how it was to be, these flights foreshadowing the relationships ending.
Back in London, I actually went back to the job I had left six months before, and we stuck with the plan that he would soon join me. We talked on the phone a lot, I cried a lot, and we assured each other that we loved each other. With my friend having put a fly in the ointment with my flat, I was sleeping on my brother’s couch until she relented. The time difference felt more divisive, he was busier, and I missed him. I missed my life there, the foreignness of it, the moments I suddenly realised “I live in Chicago”, the idea of a future.
Then things changed, he set up his own record label with two friends, and eventually he admitted there was to be no move to London. He did fly out to visit, and I flew out to combine business in New York with flying to Chicago to spend time with him, but it was clear that there were too many obstacles to us being together.
I was heartbroken, but I had had an incredible adventure, met some amazing people, and I had tried. It didn’t work out, but at least I had tried, no ‘what ifs’. I recognise this part of me driven to leap into things, relationships especially, based solely on some gut feeling. I never looked before I leapt, I was impulsive, adventurous, bold, brave even. Despite the many ways things went awry, these initial attractions, the idea of adventure, would continue to draw me in. The promise of that glint, that ‘shiny thing’ I saw turning out to be a real treasure, the fairy-tale ending. That inquisitive, optimistic magpie.
I have some dramatic idea that on my deathbed, or standing in front of the bus that hits me, I will be comforted by having made some bold choices in my life. Rightly, or wrongly.
Love this, Kay. Glad you were bold and went for it. And even more so that you'd do it again. It's so much better than a life of regrets.
Ps. How about "Sfaxing"?! 😊