I went from serial monogamy to serial dating—here’s what happened

I was a late bloomer. In high school, I was the epitome of an earlier years Taylor Swift song—always on the outside, but knowing he belonged with me. Although I had a boyfriend for a brief stint my sophomore year, my school dance cards were typically filled with friends and pre-selfie pictures taken with disposable cameras that dictated a picture taken was worth one of the limited frames.

College brought the stop-start dance that is early twenties dating, and I didn’t excel in the choreography. Either I didn’t have the right dance partner, or I was overthinking my way out of step, I could never quite get the hang of the “hangout.” The language of dating was confusing: “talking,” “chilling,” “friends with benefits”—what did it all mean? As I fumbled my way toward fluency, I kept wondering: what happened to dating? I’m talking about the go-to-a-restaurant-and-take-a-stroll-in-the-park type of courtship that seemed to be missing in my generation. My college years were a well-versed experience in this pseudo-relationship science. Before my junior year, I had a summer romance (as one often does), that turned into a two-and-a-half year relationship, which resulted in me moving across the country post-graduation in support of my partner.

When that relationship (arguably my only serious one) ended six months post-move, I was lost. Once healed from the heartbreak that accompanies the end of a relationship, I panicked. How was I going to start dating again? I hadn’t been particularly fond of the process before, and now my hiatus had left me with an all-over rusty feeling. I was in a new city, where the only people I knew were co-workers decades older, and long since married. With much trepidation, I decided to go online.

My mind was blown. So many choices! I crafted my profile with great care, and a ton of honesty. My breakup, although necessary, had at the time been a shock. The months following, I spent a lot of time in self-reflection, both in what had gone wrong, and a re-evaluation of what I wanted. I realized that a lot of my time in previous relationships had been catering to my partner’s needs; sometimes the caretaker needs to be taken care of.

Dating a bunch of people happened by accident. Online searches for love matches can be tricky, and also quite laborious. But it can also be a lot of fun. Some interactions would not progress past the first date; others would result in a few months of companionship. Once I regained my footing, I re-learned how to date. Without the pressure of long-term labels, I was able to enjoy myself. I said yes to dates with different people, no longer devoting all my energy to a person who may not be equally invested.

It’s important to note, however, that dating and being in a relationship are two separate things. For me, dating was enjoying activities with people with whom I had a shared interest, without the pressure that comes with exclusivity. As long as you are completely honest with your date from the beginning, it can result in some amazing adventures that you otherwise may have missed (with the added benefit of organically getting to know someone with whom you might possibly have a relationship with in the future). It can also result in a crazy schedule—like that time I accidently agreed to two separate dates at the same time thanks to a glitch in my Google calendar. Or the time that I saw my Friday night date when out on Sunday afternoon with another suitor (awkward, but don’t worry, he was with his own date).

Dating a bunch of people isn’t for everyone: you have to be extremely honest with yourself about what you want. If you are, it only aids in your own personal growth. I learned so much about myself during this process, and became more confident in seeking what I wanted (and feeling okay with turning down things that I didn’t). This newfound comfort in my own skin is what initially attracted my now-husband, a former participant in my multi-dating adventures. When I met Ben, I was forthright with the fact that I was seeing other people. After a few dates, I stopped, realizing I didn’t want to date anyone else. When he asked me a few weeks later to become his exclusive girlfriend, I felt ready to fully engage in a committed relationship. Dating allowed me to reclaim my own love life, and finally learn to love myself.

[image via Searchlight Pictures]

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