The Worst Breakup I’ve Ever Had

I’ve had quite a number of long-term relationships. So, I’ve been through the wringer just as many times. I don’t know if that qualifies me to be an expert on breaking up, but let’s just say that I’ve seen it all.

I’ve heard the “It’s not you, It’s me.” I’ve broken up and then continued living with an ex for a month (don’t do that). I’ve moved out on my birthday to take a break. I’ve had a last hurrah vacation to Vermont. I’ve received the text break up and the not-so-subtle ghost. I’ve even had a few mature, sit-down-and-talk breakups as well.

Some of those were more painful than the others, but the worst, most soul-crushing breakup I’ve ever had happened back in 2011. It took me forever to climb out of that hole of depression, but it did help me learn a few things too.

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The Beginning of the End

Let’s take a trip back in time to a state that apparently is known for its gardens. It was Summit, NJ. It’s a wealthy waspy town, and I used to joke that we lived on the wrong side of the tracks. Technically, we kind of did. If you were near the hospital, it was where the less wealthy people lived.

My ex-girlfriend and I had moved into the second floor of a house right by the park. It was pretty nice for what we paid. The three-story house was basically divided into three apartments. For some reason, it had been decided that we needed a two-bedroom apartment — so that she could have her own room to get dressed and do make-up. We had a huge kitchen, dining room, living room and even a little sun porch that I used as a smoking patio.

For the purpose of this story, I’ll call my ex Erin. We had been dating for around a year and a half when we decided to move in together. This would be the second time that I’d lived with a long-term girlfriend. When we moved in together, we were trying to act grown up and decided to spend a little money on furniture, Raymour & Flanigan furnished the living room and dining room.

A buddy helped me move all of my stuff from Hoboken, and then we grabbed all of her belongings from a town 15 miles away. I gave her free reign over the decorations; I just wanted to have a say on the couch. We decided upon Summit because it was equidistant from each of our offices (as the crow flies). In reality, my commute into lower Manhattan ended up taking three times as long as her drive to a corporate office park.

After about a year living there, the relationship had started to head in the wrong direction. Neither of us were really fully engaged or happy. I was often working 12 hour days with an 1.5 hour commute each way. A lot of the time, I was able to have dinner, knock a few drinks back and then it was time for bed.

Where’s the Ring?

We had grown apart and only had sex once or twice a month, which was partially my doing. Either my mind was occupied by work, I was busy drinking or I just didn’t want to in the moment.

Her younger brother had just gotten engaged, which turned up the heat on me. Not only was she hinting and nudging that she wanted a ring, but her family was too. Her entire extended family turned to me during Thanksgiving dinner and asked when I was going to become part of the family.

I know their hearts were in the right place, and they were showing affection, but, in the moment, I was mortified. I felt like my back was up against the wall. That was probably the beginning of the end, honestly.

At this point, I’m going to guess that Erin was around 31, and I was 32. The engagement discussion started to become more explicit and filled with ultimatums. It was clear that she wanted to get married, immediately have a child and likely live in New Jersey near her family for the rest of her life. We had discussed moving out to my home state of California, but I never really felt like that was on the table.

Over the next few months, I started drinking more, and we started arguing more. Looking back, I know realize that some of my behavior (causing arguments, substance abuse) was my way of coping with the pressure that I felt from her as well as my increasing work responsibilities. I couldn’t recognize my feelings, and I was scared to let the comfort of the relationship go. Realistically, we should have ended it well before that.

We got into a blowout fight on Super Bowl weekend with plenty of yelling. I remember telling her that I was never going to be her father and that I didn’t want to live in New Jersey for the rest of my life. We both had business trips the day after the Super Bowl — so we were going to give each other that time to think about the future.

When I flew back the following Friday from San Francisco, it was an early flight through O’Hare. I got stranded for more than 8 hours. I tried to drink off a hangover from my night out with the clients. I’d talked with Erin a few times during that week, but the conversations seemed to devolve into an argument every time. I decided that I need to get myself well lubricated for whatever I was about to walk into.

The cab from Newark airport dropped me off around 3 am Saturday. I had a headache and just wanted the day to be done. I could see that the lights were on as I climbed the stairs, which I found odd. Erin usually went to bed early. And then I opened the door…

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A Stealth Exit

Everything she owned in the apartment was gone, except her dresser. There was a pink Post-it note attached that read, “I trust you can take care of this. I don’t want it.”

Closets empty. Bedroom furniture gone. No shoe rack, no jewelry stand. No books, no mirror and desk. Just dust, some wires and hangers on the floor.

I broke that dresser into little pieces in the parking lot. I wonder what the neighbors must have thought about me going Medieval on some cheap Ikea.

I would later learn that her entire family had moved her out of the apartment while I was in San Francisco. It was a coordinated affair. I was devastated. Completely broken. I proceeded to binge drink for the next several months.

I felt like I had been surgically removed from her life like a cancer while under general anesthesia. The way that the exit had been choreographed in secret made me feel like I was a criminal offender who would get dangerous if she broke up with me in person.

“What did they expect me to do exactly?” a horrified younger self wondered.

Today, I can admit that, at that very moment, I was in the process of developing a significant drinking problem that was impacting our relationship. I was incredibly immature and didn’t know how to communicate my feelings. I was confused and felt trapped. I didn’t want to make the wrong decision about marriage — so I had been stalling.

My inability to give a voice to these feelings led to a significant amount anger and arguments, but I had never and would never lay a hand on her. In my mind, physical violence toward a woman is just forbidden — no matter how bad things get.

But none of that mattered. I felt I’d somehow been proclaimed guilty — in a trial that was held without me. I only discovered my sentence when I showed up hungover at 3 am. The shock of it broke me. It took me well over a year to recover.

A four-year relationship ended with a Post-it note.

She came by to give me the talk a couple of times a few weeks later. Each time, however, I was in the middle of an all-weekend bender so the conversation has hopeless. I’m sure it was depressing for her to see me such a mess, but she had seen it all before. And it was part of the reason she had left.

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What Did I Learn?

It was some time before I was ready to learn any lessons. I developed tunnel vision and poured myself into a new job and moving into Manhattan so I could shrink my miserable commute.

Once I finally examined the truth beneath the pain and the anger, I realized that drinking had made me numb and miserable in the relationship. If I needed to self-medicate my anxiety and work stress by getting drunk, then what kind of person was left over? How could I give someone else nothing but a shell of myself? I would never be capable of loving someone else unless I quit drinking.

I finally came to understand that she did what was best for both of us. I was not strong enough to end it myself. She tore the Band-Aid off as quickly as she could (apologizing later for her surgical approach). Everyone has their own process of handling difficult situations, and she did what she felt was best in the moment. Her doing what she did was exponentially better than us getting married and having a child — only to get divorced a few years later.

The primary lesson for me was that I should never stay in a relationship just because it feels comfortable or secure. If you’re going to commit yourself to another person, the question is really whether or not you see a genuine long-term future — a future where there is room to grow. More importantly, do you accept the person for who they are? Do they accept you for who you are?

Bad relationships can often come down to a question of control. It’s problematic when love is given only if you act a certain way, if you change to conform to the partner’s demands. That’s conditional love. It relies entirely upon being something that you’re not, and that’s only a recipe for long-term pain.

As for me, I needed to do a ton of work on myself. I needed to take a hard look in the mirror and expand my focus from the job. I started to do that a year later when I quit drinking the first time, but it was short-lived. It would take me another seven years to turn the corner and learn to accept myself.

Drop a line if you’d like to hear more relationship adventures.

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Previously published on “Hello, Love”, a Medium publication.

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