scorecardI moved from Seattle to Chicago to try again with my ex. It was rocky at first, but it worked.
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I moved from Seattle to Chicago to try again with my ex. It was rocky at first, but it worked.

Luke Brennan   

I moved from Seattle to Chicago to try again with my ex. It was rocky at first, but it worked.
LifeScience3 min read
  • My college girlfriend and I broke up after graduation because we moved to different cities.
  • Two years after our split, I still couldn't stop thinking about her, so I reached out.

I remember exactly where I was: sitting with sweaty hands by a canal in Seattle, surrounded by trees. It was late in the afternoon and uncharacteristically sunny, even for June. A perfect time and place for relaxing, but I was not relaxed.

In front of me was a text message, all typed out and ready to send to my college girlfriend. We dated for two years and broke up after moving to different cities post-graduation. It'd been two years since, and despite my efforts, I'd been unable to keep her off my mind.

The text briefly explained how I was feeling. I wanted to let her know that I was thinking about her, had been for a while, and wanted to see if she had any of those feelings, too.

"No worries if not."

"Honestly, you don't even have to reply."

It was a strange feeling, watching my thumb hover over the phone, knowing our lives could go in completely different directions based on one silly paragraph.

I deleted the bit about not having to reply and hit send.

I flew from Seattle to Chicago to see her

A few weeks later, we met for dinner in Chicago, where she was living. It was great to see her, but I was nervous, and the conversation was slow to start. The whole time I wanted to ask her what she was thinking, whether or not she could see this going anywhere. But we stayed away from anything personal and instead talked about jobs, weather, Chicago, Seattle, our food, and pretty much anything other than each other.

When we left the restaurant, I felt my stomach sink. Did I miss my shot? Dinner went by so fast, and we hadn't talked about much. I walked her back to her apartment feeling like I was running out of time. When we stopped at her door, I started to say goodbye, not knowing when I would see her next.

"You don't have to go," she interrupted. "We can keep talking."

We stared at each other for a moment before she turned to unlock the door to her place.

We sat on the couch with a healthy distance between us. As the night wore on, that distance shrank, grew, and shrank again. We talked for hours, and slowly, we opened up, getting more personal and making jokes with each other. We laughed about how crazy it was that we were talking again — we had gone on a date again! — and about how absurd it would be if I moved to Chicago.

"I could move here, you know." She looked at me, unreadable, and nodded without smiling.

When I left her place that night — her head peeking out from behind the door as she said goodbye — it was clear that we still had something. And I wanted to figure out what it was.

I moved to be closer to her and try again

I moved to Chicago a few months later. My friends in Seattle were baffled. Some had a lot of questions: Is she excited? Are you excited? Are you guys dating? How, exactly, is this going to work out?

After a few months, we weren't sure if things were going to work. Both of us had moments of doubt, and a couple of dates were almost disastrous.

The worst was a trip to Zoo Lights — Chicago's Christmas-light-show extravaganza. Surrounded by couples holding hands and sipping hot chocolate, everything around us looked romantic. But something was off between us. She pulled out her phone, I disengaged, and our night dissolved into a silent walk home.

"Why isn't this working?" I asked.

She started crying.

Far away from all the lights and festivities, we stopped to talk on a bench. We agreed that we both cared about each other — but was that enough? What if we just weren't compatible despite our feelings?

We almost broke up that night.

We had to talk through our entire past relationship

The turning point for us was New Year's Day. We were driving back from a party in Milwaukee and decided to go through each part of our past relationship that caused it to end (a strategy suggested by my therapist). It was a two-hour drive, and we talked the whole time: bringing up all the hurt, all the things that didn't work, everything that we were afraid of, both then and now.

When we finally got back to Chicago, snow was falling in big, chunky flakes. The streets were beginning to get covered, and yellow light from street lamps had to make its way through a layer of thick snow. We parked and sat in her car, just holding hands and looking at each other. At that moment, though we didn't say it then, we both felt understanding and understood, loved and loving, and finally, it all made sense (again).




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