Single Girl Series: Part I

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Editor's Note: We are going to be following Chelsea's journey for the next six months as she navigates single life in the current world of Tinder, hook-up culture, and single-shaming.

Words by Chelsea Oliver

I sat on my bed with my back against the wall while I stared into the nothingness that was my room and breathed deep. I had recently broken up with my boyfriend of five plus years and was single for the first time in my adult life. No prospects. No intentions. No plans.

Aaron* and I had met in college. We were barely friends when I made the leap and gave my number to the guy who was obviously in every sense, the male version of myself. We spent the next five years making things work. There is no doubt in my mind that we were at one point very much in love but now looking back, it constantly felt like we were working to make something last longer than it was probably meant to.

We were the kind of couple that seemed "perfect for each other" and at a time, we very much were. But when I told him in January 2015 I wanted out of the life we were still working on building, I felt like a bitch who never deserved a man like him in the first place.

He was street-smart and highly educated. He had a decent job and plans of furthering his education with a doctorate degree. He had his own car and apartment, and relied only on himself. He was driven, good looking, and well dressed. He had the biggest heart of anyone I ever met and was effortlessly well liked by everyone. And when we were in the same place at the same time, he worshipped the ground I walked on. 

But at some point, I realized I felt like a single lady more than I did a queen to the man I loved with every ounce of my being. I wanted out.

To be fair, at this point in my life, I had not lived up to the plans that Aaron and I made. I had recently earned my Master's degree, but had yet to find a job that lived up to my own potential. And I made our bit of distance much more difficult by moving three hours away from him because I could no longer live with my parents. Where I needed support, I was given lectures and where he needed the strong woman he thought he had, I gave him a mess of a person.

We were no longer perfect for each other and I made the decision to end it before we started to really resent one another. I wanted this perfect man to remain my friend because for the past five, he made sure to show me countless times that he was the best friend I ever had.

I surprised myself on how quickly I jumped into my singleness and starting dating. But in my defense, I had felt like Aaron was just a friend for the last couple years of our relationship. So we broke up at the end of January and by April, I had allowed myself to have my first crush.


Matthew* was three years my junior, had the sweetest blue eyes and a sheepish smile. He was a hard-working country boy and my city girl attitude did not know how to approach our growing curiosity of each other while his friend group meshed into mine and seeing each other became more frequent. 

He was the first person I let myself like and can be explained only as the perfect soft place to land after breaking my own heart. Matthew was the nicest guy in his group. He was taught well about how to treat a woman and it showed when he picked me up to take a ride in his truck after our separate Mother's Day celebrations. Overall, our time together was short. While I harbor nothing but respect for him, he very much was too young for me.

Little did I know at the time, I had a large amount of growing up to do on my own as a newly single woman. And I had no idea that it would be almost another two years of dating before finding what I had wanted all along.

*Names have been changed to protect the privacy of individuals. 

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Chelsea Oliver is a lover of life in heels, coffee in hand, who runs the marketing department of a credit union by day and makes sassy stationery for her own business by night. Chelsea is an old soul in a power-lifting millennial body. She craves authenticity while loving every filter on Instagram and tweeting in all caps as necessary.

 Relationship | Dating | Single | Break Up


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