UNPOPULAR OPINION: It's OK to Date Your Best Friend's Ex

I was torn between being a loyal friend and opening myself up to the possibility of experiencing real, true love.
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Kate Muller
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I was torn between being a loyal friend and opening myself up to the possibility of experiencing real, true love.

When it comes to dating, there are rules. Rules, in no particular order, like:

  • Don't come on too strong.
  • Don't pretend to be someone you're not.
  • Don't date your best friend's ex. 

I've opted to interpret that last one as a loose guideline rather than a hard and fast rule. I guess that makes me a rebel? (Or a bitch.) Either way, I'll start from the beginning.

I grew up in a small town. I'm talking John Mellencamp small. It was the type of place where everybody knew everyone else's business and one's privacy wasn't so much a right as it was a privilege. My high school graduating class was one of the biggest the town had ever seen – a whopping 100 students. To put that seemingly low number into perspective, my older sister's class graduated with less than 50. 

Like I said, small, small town.

My coming of age climb from kindergarten to 12th grade certainly wasn't a lonesome one. For the most part, I graduated with the same kids I'd played Red Rover and tag with on the playground. Between the ages of 6 and 18, we kids were pretty much forced into establishing ourselves as a tight knit group. As a result, my friendships go way back. I'd met my lifelong friends at a very young age, and while I'm not incapable of making new friends, I've always felt an intense loyalty to my small town comrades.

By the beginning of my senior year, one of my best friends had started to date a guy in our class. He palled around with the popular boys in our grade, most of whom were bad news even back then. Still, I could tell that he was different. He was smart, he was friendly, and most importantly he seemed to have a conscience. In my opinion, he was one of the good ones. Which is why it was especially hard for me to watch my friend emotionally murder him.

Their relationship was one of the most toxic displays of "love" I'd ever witnessed. Don't get me wrong, my friend would lend me a helping hand or provide a shoulder for me to cry on anytime I needed it, but she was notoriously high maintenance when it came to relationships (and a little nuts.)

She'd snap at him over the silliest things and always toted a bag full of jealousy around with her. Looking back, I think she was just unsure of herself and probably a little bit insecure. But weren't we all at that age?

Near my small hometown. 

Near my small hometown. 

By winter, I'd snatched up a boyfriend of my own and my awareness of their unenviable situation morphed into anticipation. Any time our group of friends would get together, I couldn't wait to be entertained by the show that these two would undoubtedly put on for us. 

We eventually graduated and everyone left our small town in search of new opportunities. After committing ourselves to separate universities that required a day's worth of travel to visit one another, my high school boyfriend and I split up during our sophomore year. Meanwhile, my friend and her boyfriend were continuing to live their miserable lives together at the same college. I'll admit, back then I was jealous that they'd opted to go to the same school. After all, didn't that mean their relationship had a better chance of making it? Apparently not.

It wasn't long after my breakup that their relationship ended, too. 

Post-breakup, I maintained a single lifestyle while my friend transferred schools and almost immediately started dating another guy. Still, we managed to sustain our relationship through college even though we were miles apart. We didn't talk every day or even every week, but she and I both knew that we had the type of friendship that could stand the test of time.

After the pomp and circumstance of graduation, it was back to the small town. None of us wanted to return home, but with very little money and an incredibly tough time landing entry-level jobs during the recession, living on our own just wasn't an option.

Back home, I started to see a lot of people from high school at the local watering holes (because there were, like, only two). My friend's ex and I started to run into one another regularly at a weekly trivia night that one of the bars hosted. We'd chat, reminisce, and catch up on old times. For the record, I never had any sort of romantic feelings towards my friend's ex prior to this. Hell, I just thought he was a nice guy! But suddenly, I was seeing him in a whole new light.

He was cute, he was charming, and (dammit) he was funny! It didn't take me long to realize that I was falling head over heels for him – and fast. But their breakup hadn't been mutual. After three or so years of fights, hostility, and a general feeling of unhappiness, he'd broken up with her. I knew that there was still bad blood between them. I was torn between being a loyal friend and opening myself up to the possibility of experiencing real, true love.

I know what most of you are thinking. There are literally billions of people on this planet and a whole world outside the bubble of my small town, so why was I willing to risk my friendship? Was I just being selfish? Maybe.

To be fair, my budding relationship with my best friend's ex came about during an incredibly confusing time in my life. I was one year out of college, I was once again living under my parents' roof, and I was still trying to figure out what the hell I was going to do with the rest of my life. Honestly, dating wasn't even on my radar.

Eventually, I opted to proceed with caution. I wasn't going to allow myself to fall any further in love until I had the chance to talk it over with my friend. If she'd had a problem with it — and why wouldn't she have a problem with it? — I would've respected that and backed off. The only thing I knew for sure is that moving forward without her consent was not an option.

By now, she was still dating the same fella she'd hooked up with after being dumped in college. And while she still seemed to hold a bit of a grudge over the split, she was infinitely happier in her new relationship. Plus, at this point, she'd been dating this new guy longer than she'd dated her ex.

We met up one night after work. I'm not sure if I was trembling because of the words that were about to spew out of my mouth or because I was terrified of what her reaction would be. Either way, the butterflies in my stomach were fluttering around like they were on crack. Once I mustered up enough courage to broach the subject and just spit it out, I was shocked by her reaction. Not only was she positive and willing to talk this whole thing out, but she wasn't throwing her drink in my face.

By the end of the night, she had given me her blessing and seemed genuinely happy for me, although I sometimes wonder if she regrets being so agreeable so darn quickly. After all, had she really had enough time to process what I was saying? Or maybe she wasn't really thinking long-term. Who knows. 

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Fast forward five years and my best friend's ex and I are currently engaged to be married. Crazier still, she'll be standing up there with the both of us come November as one of my bridesmaids. (She married her man last year. I was in her wedding, too.) I realize my situation is unique and there are many other instances of ex-dating that should probably be avoided. But I think it was my candor and honesty that allowed me to metaphorically have my cake and eat it, too. To this day, I wouldn't change a thing about the way I went about it.