My (Ex) Best Friend Married My First Love

Little did I know it wouldn't be just me who wanted a future with him.

By xoJane — Written on Nov 20, 2022

Photo: Natalia Lebedinskaia / Shutterstock

Jordan* was my first love in that perfect, nauseating, after-school WB television show story arc way. I didn't know then that my best friend married my first love after our eventual breakup.

We first became friends in our Saturday morning driver’s ed class, sharing the same boring instructor while anxiously navigating the winding roads of New York City’s suburbs.

Friends led to best friends, and after being separated for a high school summer, we realized we were in love. It was butterflies and hand-holding and everything a teenager falling in love is supposed to be.

We had sex for the first time in the early hours of January 1, 2000. I was head over heels.

As fate often has it, our young love had the odds stacked against us. I was a year older than Jordan (a cougar even at age 17) and left for college in Boston when September rolled around.

Although I had convinced myself that our love really was as strong as Savage Garden described in “I Knew I Loved You,” we only made it as far as winter break.

He broke up with me in a mall parking lot and I remember that I actually thought the world was going to end while I waited for my dad to pick me up at Barnes and Noble. It would be years before I saw him again.

Jen* was the quirky, gothic yin to my insecure, Abercrombie-wearing yang... and the first person to befriend me in gym class when I changed schools at the beginning of 8th grade.

We were an odd pair, our own version of Rayanne and Angela, but we were best friends through thick and thin. She even hooked up with Jordan’s best friend when we were dating, and since she spent so much time with us, we thought it would be fun to be a pair of couples eating dinner at Applebee’s.

Despite all that transpired between us, I’m thankful for knowing her in my formative years. She pushed me to break the mold and leave my comfort zone.

My friendship with Jen endured the four years of college distance and was stronger than ever.

When she encouraged me to move to New York City after college graduation, I listened. Many of my first nights in NYC were spent sleeping on a couch in the studio apartment she shared with her boyfriend.

It was during this time that she hatched the plan for me to try to date Jordan again. He was starting his last year at NYU, and of all the apartments in Manhattan, it turned out I had found one a mere five blocks from where lived.

Little did I know it wouldn't be just me who wanted a future with Jordan. Jen and Jordan celebrated their 12th wedding anniversary this fall.

In 2004, the options to casually contact your ex-boyfriend to rekindle your relationship were not as varied as they are today. Facebook was barely out of the gate, smartphones didn’t exist yet, and if you had asked someone about tweeting, they probably would have thought it was a sexual act they hadn’t heard of before.

There were really only two options: phone or e-mail. Inspired by the Sex And The City poster hanging in my bedroom, I started with a Carrie Bradshaw-inspired e-mail from my Hotmail account.

While I can’t remember how many e-mails it took, Jordan agreed to meet me for wings and beer at a local bar. I was thrilled.

Over the course of my first summer in New York, my friendship with Jordan picked back up where we had left off. He had just started dating someone and I respected that. I was happy to have him back in my life, even if it wasn’t romantically.

I quickly joined his circle of friends and settled into the life of a broke, recent grad in the East Village. Working for an event company, I would bring home huge platters of leftovers and feed Jordan and his roommates in my tiny living room.

We became regulars at a local bar where the beer was basically free and you had to roll your pants up to use the bathroom. It was a far cry from the life Carrie Bradshaw had promised, but I was happy.

It was already the middle of that summer when Jen’s relationship with her live-in boyfriend imploded. They had been struggling for a while and she found out he was planning a move out of state behind her back. She was understandably devastated.

In my efforts to help her pick up the pieces and cheer up, I encouraged her to spend more time with me, Jordan, and all the new friends I was making. The next few weeks were a blur of bars and watching the sunrise from the tar rooftops with my best friend.

It was an amazing summer and Jen was getting over her terrible breakup. In the midst of our summer revelry, Jordan’s new girl had broken things off with him. We had settled into a new friendship and things were back to where they were before we dated.

One afternoon we were out with Jen and a group of our other friends. Jordan approached me at the bar and said he had something he wanted to talk to me about. He had feelings for Jen and he wanted to ask her out — did I think she would be interested?

I remember feeling like the floor was going to fall out from under my feet. I told him that I didn’t think she would ever do that since we had dated. I was wrong.

The weeks that followed included conversations with both of them separately and together.

I told them that I couldn't promise nothing would change if they dated because I wouldn’t know how I would feel until it happened. I also told them that I would never stand in the way of two people who had feelings for each other being together.

Finally, I told Jen that she’d better be sure she was going to marry him and not just hook up with him if she was going to put our friendship through this.

One night, a mutual friend told me that Jordan and Jen had already been sleeping together for a month. Everyone in our group of friends knew except me, and she had just found out and couldn’t keep it from me. I was devastated.

In the end, what hurt was being lied to, not that Jen and Jordan ended up together.

I left the group of friends and distanced myself from both of them. I learned that Jordan moved into Jen’s studio with her less than a week after I found out they were sleeping together.

I tried to spend time with Jen, but it was too painful to pretend that things could ever be the way they had been. She wanted her best friend Leah and her new boyfriend Jordan. Unfortunately, she had lost one of those people in her desire to get the other one.

Nearly a year later, I met Jen for brunch one day. She told me that she and Jordan had been talking about getting engaged and asked me if I would mind. I told her I wouldn’t mind as long as she wouldn’t mind having a husband who had lost his virginity to me.

Despite the shade, I was throwing her way, she asked me right there if I would consider being her maid of honor. I told her I needed to think about it. Eventually, I agreed.