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Sex + Relationships

My Side, His Side, and The Truth: Why Didn’t We Work?

A little-known fact about me is that I have actually been in love before. Was it like the movies? Simply put, no. We were far from that of Lara Jean and Peter Kavinsky, but we were young, he was athletic, it was intense, and it was ours. 

This week I had the opportunity to sit down with my ex-boyfriend, Shawn, in an attempt to dissect my last relationship in order to learn more about myself. Similar to the 2018 viral video, “Hurt Bae,” but without the toxicity and disrespect. 

Enter Shawn. Now one of my best friends, Shawn is what one may consider to be my high school sweetheart. We dated for two years between 2016 and 2018, and I would be lying if I said my years spent with him were anything short of magical. We did it all from sweet 16s, the tear-jerking promposal, and football games, to highschool spirit day, holidays, and graduations. Anything big that occurred during that era, Shawn showed up. 

After acknowledging all of our good times and finally coming down from the high of serotonin that so often accompanies nostalgia, we were forced to confront the uncomfortable, frequently avoided topic of conversation: the breakup.  We unpacked our relationship, took accountability, and eventually answered an essential question: Why didn’t we work? 

We came to an explanation for the unfortunate conclusion of our relationship by dissecting our rights, our wrongs, and the manner in which they were processed by one another.

First, we discussed the positive: what worked about us? 

“Nothing felt forced with you,” Shawn began. “Our relationship developed very easily. I enjoyed your company. We had different perspectives, but that just meant that we had a lot to teach each other. You broadened my view a lot.” 

We easily agreed on this topic. Shawn and I met, clicked, and it was history. We went from exchanging (many) wordless glances in dull-toned hallways to talking on the phone for 5 hours on our first conversation. 

In my opinion, Shawn and I worked because I always felt safe around him and because we were friends first; there was no topic of conversation we danced over, and there was no awkward silence when trying to explore the connection beyond the romantic level. A genuine, organic platonic foundation is underrated and often forgotten when cultivating romantic relationships, but it’s ultimately the reason why me and Shawn are able to maintain the bond we have to this day, and for that, I’m thankful. 

Then, we got a bit more serious: what didn’t work?

It was a blunt answer delivered in unison by the both of us: “not communicating,” 

Shawn admitted he intentionally failed to disclose certain pieces of information to me, due to believing that obscuring and (conveniently) leaving out certain details was just the easier road to take rather than that of honesty. Typical, I thought to myself, but nonetheless I was appreciative of the acknowledgement.

Though usually I enjoy dwelling in my own victimization and innocence in my spoiled romances, I had to admit I wasn’t off the hook. My lack of communication existed in my failure to express my true feelings at times. Despite how vocal I am as a woman in my 20’s, I’ve had my fair shares of “nothing is wrong”, “I’m fine”, and even just plain silence. However, it is because of my years spent avoiding difficult conversations that I heavily emphasize and encourage a constant flow of open communication now. 

Moving on, it got a little more specific; what could you have done better? 

“I should have prioritized my personal goals more- not only for you, but for myself.” 

If I were to describe the contrast in work ethic between Shawn and I, he would be the guy in Highschool who walks around with a seemingly empty backpack; the guy who always seems to need a pencil, but still manages to get an A+ on a calculus test just because they’re hyper-talented at retaining information. Meanwhile, I would be the girl who has four sets of color coded notes and a quizlet folder filled with practice tests for exams that haven’t even been announced yet.  The contrast is both comical and undeniable.

I sighed in relief when he shared his concerns about his priorities because I always feared our difference in work ethic would extend into our relationship. It didn’t, but I can say I feel like it initiated the process in which we grew apart indefinitely. 

This next one stung a little bit. What could I have done better? 

“You had the tendency to be very possessive,” Shawn answered almost right-away. This is a moment of complete vulnerability, and I agree in totality with Shawn’s critique. I may or may not have given too many of his female friends the side-eye unnecessarily. In my defense, dating an extremely talented corner-back in highschool is a war all on its own, and a war I was determined to win (and did.)

From your perspective, why did we break up? 

Shawn took me through a brief recount of that September day that brought to both of us an immense amount of heartbreak. It was an argument about my failure to communicate with him for an entire day; something he’d never known me to do in the two years of us being together.

In my defense, my distance can be attributed  to being distracted by all of the glories of Hampton University’s New Student Orientation Week. He recalled feeling angry and hurt that I no longer seemed to have an abundance of time to cater to him due to my being a college freshman at the time. 

In response, I shared that I was more so hurt than angry; I felt like he wasn’t happy for the new journey I was embarking on, a journey of which if nobody knew the magnitude of joy I felt for,  he did. I felt like he was being selfish, and naturally, jealous. 

“I hated you for a while,” Shawn confessed. Ouch. 

Nonetheless, I never hated him. I told him I was hurt, but eager to move on and explore the world ahead of me, and I did. I can recall our separation feeling more like a divorce than a highschool breakup: chillingly final and undoubtedly unsettling. I was shaken to my core. 

I didn’t wallow for too long, only because I truthfully couldn’t find the time to even do so. Looking back on it, I believe the strength of our friendship allowed me to mourn the end of our romance peacefully because I realized it was just that rather than the demise of my knowing Shawn altogether. I always knew he’d be back, even if he didn’t know it himself. 

The last question Shawn and I answered was heavy, but essential: what was one thing you wish you knew about how you felt during those times? 

“I wished you knew that I was always on your side, even when it didn’t seem like it.” 

His words brought me the same security I relished in when I was 16-years-old. The statement evaded the room and wrapped itself around me like a blanket made of teen spirit; I needed it, and then I found myself hating him for being so good at just being there, and then I hated myself for having yet to encounter another with the same skill. 

I didn’t tell Shawn what I wished he knew about how I felt, but I will now. 

I wished you knew that you have left very large shoes to be filled in my universe of obligation, and I often worry that nobody will ever be the right size again. 

So, why didn’t we work? 

If you ask Shawn, he’d say that my leaving Boston, MA to attend college in Hampton, VA was detrimental to the version of myself he’d become accustomed to for so long. He’d say that the distance altered the dynamic of our relationship to an extent that it was unrepairable. He is not wrong.

If you ask me, I would say that we didn’t work because my communication skills deteriorated dramatically. I’d also say that for the first time ever, I chose myself. In the same manner in which I was possessive over my boyfriend, I became possessive over myself. I’ve yet to regret it. 

If there’s three sides to every story, then truth will lie somewhere between the contrast of our own perspectives. The truth is that we didn’t work because of the physical distance and the inevitability of my own need to grow as a woman outside of the relationship. 

Shawn is the best-first-love a girl could ask for, and the friendship, laughter, and loyalty between us is something I will never cease to cherish. Even though our romance was many, many moons ago, the reflective nature of our conversation was therapeutic to say the least. We laughed, we (I) cried, and more importantly, we came to the conclusion that the love and respect we have for one another  -even outside of the emotional trainwreck that is highschool- is positively enduring and undying, and that, if nothing else, works for me.


Cheyenne Paterson is a senior English major, Strategic Communications minor studying at Hampton University from Boston, MA. She aspires to combine storytelling and an editorial style of writing to increase audience engagement and advocate for brands and corporations. Cheyenne is the Editor-In-Chief for Hampton University's Chapter of Her Campus, a regular contributor to Impressions of Beauty, and the President of the Peer Counselor's organization on campus. In her free time, Cheyenne enjoys dabbling in interior design, perfecting her homemade coffee, and baking new recipes!
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