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Disappointing First Dates Made Me Love Myself More

I wont apologize for standing by my values.
STYLECASTER | Bad First Dates

In the summer of 2021, I transferred into NYU and moved to the city of my dreams, wide-eyed and optimistic about the beginning of my young adult life. I was entering my sophomore year of college, which meant living in my first apartment, cooking my own food, and holding down a true (albeit minimum wage) job. And like most new college recruits, dating was also part of this novelty for me. There was suddenly a fresh “batch” of eligible singles I could meet from my school and the wider NYC scene. The pure potential of that was intoxicating—I didn’t even think to have bad first dates on my radar.

Anyone who lives in environments in which finding love can be tricky (hint: big cities) will tell you that meeting someone online is as good an option as any. By picking a city school, I knew I was burying the possibility of strolling around a green campus lawn and running into a funny, bookish, kind, and ultimately relationship-worthy guy.

There were no campus lawns here; only tall, oppressive buildings and the unyielding hustle. And so, I compensated by connecting with people who went to my school (or with whom I had mutual friends) through social media and responding to those who reached out first.

The period of my life that I call “random dating” had commenced.

Throughout the summer and my fall semester, I went out with men my age who were nice and interesting enough. One date had Jaden Smith’s number saved in his phone. Another filmed his own movies. Yet another (who, to my horror, detested the city’s subway system) claimed he was a high-stakes poker player. I wasn’t going for a certain “type,” which made it easier to identify traits I liked or disliked in every person I spent time with.

Going on a string of first dates also allowed me to see the city to the fullest—and, admittedly, have a fun time while doing it. Strolling through the Guggenheim, hauling a mattress down a whole avenue (don’t ask), and taking in sights of the Manhattan skyline from the Brooklyn Bridge are memories I still hold close to my heart. Yet, most were cut too short by these boys’ almost universal and fervid insistence on subscribing to “hookup culture,” a term that’s notorious enough among college students, but especially among New York college students.

Even the good dates often ended in mutual disappointment.

In this conglomerate of youthful, driven, independent, and attractive people, “casual” is the hottest word in town. A quick turnaround of romantic and sexual partners—hooking up after a few, or even one, date– is practically status quo. I wasn’t willing to give into this philosophy for my own, very firm set of reasons, so even the good dates often ended in mutual disappointment.

After each date, I’d inevitably end up walking (or being walked) home, taking a bath, reading a book, and going to bed. The morning after—alone in my tiny studio—I’d process all the feelings. The night before, I’d feel discouraged and disillusioned by the lack of chivalrous, old-school dating prospects, but the mornings always gifted greater clarity.

Rather than feel sorry for myself or disappointed in another date gone wrong, I felt immense self-love and respect for myself, grateful that I had once again reaffirmed my values and didn’t end up settling for just some guy.

After a few weeks of riding this unique, unexplainable feeling of self-sufficiency—almost like a high—I’d end up going on another date with another boy. We’d cover the bases (family, hobbies, favorite places to eat for cheap) and have ourselves a pleasant few hours. But then, the fork in the road would appear, and again I’d choose the path where I ended up successfully skirting a hookup. On my own terms, because I simply didn’t feel like it.

Women coming of age often feel a need to explain their intentions to others.

Women coming of age (women in general, to be fair) often feel a need to explain their intentions to others, a need most pressing when they either want “too much” or “not enough” of whatever it is they’re supposed to be wanting. When we follow our cravings, we are indulgent and greedy. When we choose to stay away from situations we don’t see as safe or fulfilling, we lose our fun and our appeal.

But the more I made my intentions clear on every date, without feeling the need to justify them, the more free I felt. I was being fully myself. If the person I was dating had a problem with that, then so be it.

Unfortunately, quantity has prevailed over quality when it comes to my first dates in New York City. I have still not found my funny, bookish, kind, and ultimately relationship-worthy guy. But with every new date, I gain so much in the way of perspective and appreciation for the woman I am becoming. And for now, that’s enough.

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