Everything I’ve Learned from Casual Dating at 22
By Neerul Gupta
March 5, 2024
Graphic by Caroline Clark
How many cisgender straight men think a black button-up and blue jeans compromise the perfect first-date fit? Answer: too many. Also: they’re wrong.
Dating around is in — just ask 51% of Americans. Sure, it isn’t all easy. Sometimes you’re love-bombed, other times breadcrumbed, or perhaps you’re on your fourth cycle of deleting and redownloading Hinge. The litany of red flags keeps you coming back for more, but you eventually learn to prefer green. Casual dating has its perks, and not just the one you’re thinking about.
I’m a 22-year-old queer woman of color with more rizz for straight white men than I’d known and less expertise with women than I’d like. Single and dedicated to the mingle for the past year, my casual dating life has given me the rides of a lifetime. I’m here to recount the hots and horrors of scoping out the streets, and with them, my favorite dating stories.
Dining and dancing is research
Ladies, let ‘em spoil you. Scenic rooftop bars in New York, hidden clubs on the outskirts of Rome, and the sexiest speakeasies in Los Angeles — I’ve had my fair share of freebies. And while I’ve indulged in worldwide delicacies, I haven’t always had the best of luck with my dates themselves.
Sometimes, you’re a young woman just navigating the dating scene. Other times, you’re an involuntarily appointed therapist for a lonely recent grad. Five minutes into our dinner, I knew the intricacies of his mommy issues. Ten minutes later, I downed my second glass of chardonnay. He was a sweetheart, though, and covered our check. Dinner with a therapist ought to cost $350.
Try again? Mr. CEO-of-Two-Companies-at-Twenty-Seven led me inside the Jersey restaurant that inspired “The Addams Family.” We flung flirty, feisty remarks over a candlelit four-course spread. Handsome, funny, and rich? Some things are too good to be true, and they were. After a third drink, he revealed his Trump-favoring voting history. Sigh.
While a first date definitely isn’t the place to dish out your grievances against your parents or liberal politics, I harnessed and grew my patience for many people with many issues. We all have baggage. While I don’t necessarily want to carry theirs, I could be the reason they felt a little lighter, even if for one night. Call it public service if it helps.
I’ve danced, too. Dating across the Atlantic deconstructed my Western normative dating standards. Is it really weird to bring a date, who you like, along with your friends, who you also like, to a fun night out? I’m thinking of the college student in Rome who introduced me to his friends, and off we went, tearing up dance floors across the city.
Carefree European dating enthralled me, so naturally, I adopted it. On my first date back in the States, I grabbed the hands of a digital nomad and took him dancing with me and my friends. It was a strange sight: a 6’2” white man towered over four ethnic women, each a foot shorter than him. And it was great.
Between gourmet dishes and tequila shots, I noted what I liked about the person in front of me — and what I absolutely did not. It shouldn’t be a laundry list, but knowing the type of care you desire is just as important as knowing the kind of care you offer. Sounds like research to me.
Somewhere along the road, I recentered the focus of my dates. Will they want to see me again? Turned into Do I want to see them again?
It comes, and then it goes
Not to be overly existential, but nothing lasts forever, and that’s especially true in the casual scene. But that doesn’t mean you can’t savor fleeting temporality.
Sometimes you’re grateful that it’s temporary. Let’s give a hand to the finance bro who thought the date was going better than it was. Instead of leaving like a sane person, I decided to concoct a horrible story to scare him away. For one night, I had schizophrenia. (Not my brightest moment, I know.) “Are you medicated?” he asked. “No, it makes the voices quieter,” I responded. He gave me a blank stare, and I thought I’d won. I did not. He was into it.
Other times, you fall a little harder than you mean to. I spent what were supposed to be my final two nights in Italy with blonde hair and blue eyes. (My ancestors are spitting at me, and my friends are in active pursuit of decolonizing me). I felt like I was on the edge of something new, and overwhelming emotion overrode all the analytical parts of my brain. To spend just a few more moments with him, I rescheduled my international flight. It was the riskiest decision I’ve ever taken, all for one more day of feeling. I don’t regret it at all.
Supposedly, we are meant to latch onto relationships. But learning to let go is a lesson in taking life as it comes and goes, savoring both sweet and sour. And I’m a connoisseur in letting my taste buds explore.
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There is solace in silence
So, you thought you had a good time, and your date seemed like they did too. Maybe they even told you they did. And then…silence. It hurts to be ghosted, and perhaps you channeled your frustration into crafting the perfect you-suck-and-let-me-tell-you-why text. But clicking send rarely helps more than not.
There is little payoff in manipulating meaning out of silence. Their ghostly nature need not materialize your greatest insecurities. It doesn’t mean they disliked how your eyes wrinkle when you smile, noticed the uneven curve of your hips, or were uninterested in your life — the one you’re still learning to call yours. Let the ghost pass through you and keep walking.
Consider, too, that while you’re waiting for a text back from Date #12, Date #7 is still waiting for yours. I had to gift myself the honesty of where I went wrong because I am no better than the person who, unexplained and unexpectedly, disappeared from my phone when I did the same to another. You can only sense inauthenticity in someone because it’s a reflection gazing back at you.
Vulnerability is tuition
Luckily or not, a series of bad dates makes the good ones that much better. A graphic designer introduced me to my top Spotify artist of 2023, and at his concert a few months later, I silently thanked the boy whose number I forgot to catch. The aforementioned digital nomad inspired me to spearhead my own adventures, and I have flights planned and booked across the world for the next year. As winter winds rattled his window, an artist held my gaze with a tenderness I remember with warmth.
If you’re in the casual scene, you probably won’t be scared to show a little skin. Don’t be afraid to show a little heart, either. It’s okay to lend a little part of yourself, even for a moment, even if you’re scared of how it’ll be touched, even if it’s to prove to yourself that you can. Sharing yourself doesn’t mean giving your whole self away. And if they return your softness a little bruised, thank them for the chance anyway. Vulnerability is the tuition I pay to grow stronger the skin and more secure the heart.
My casual dating era has come to an end for now. In its next season, I will continue to interpret dating as self-exploration, hopefully with more women (Ladies, my DMs are open year-round). In the meantime, I’ll encourage my fellow 20-somethings to embrace all the mess and charm of casual dating. I close this chapter of my life with great satisfaction. After all, I had a fuckload of fun. ■
Dating around is in — just ask 51% of Americans. Sure, it isn’t all easy. Sometimes you’re love-bombed, other times breadcrumbed, or perhaps you’re on your fourth cycle of deleting and redownloading Hinge. The litany of red flags keeps you coming back for more, but you eventually learn to prefer green. Casual dating has its perks, and not just the one you’re thinking about.
I’m a 22-year-old queer woman of color with more rizz for straight white men than I’d known and less expertise with women than I’d like. Single and dedicated to the mingle for the past year, my casual dating life has given me the rides of a lifetime. I’m here to recount the hots and horrors of scoping out the streets, and with them, my favorite dating stories.
Dining and dancing is research
Ladies, let ‘em spoil you. Scenic rooftop bars in New York, hidden clubs on the outskirts of Rome, and the sexiest speakeasies in Los Angeles — I’ve had my fair share of freebies. And while I’ve indulged in worldwide delicacies, I haven’t always had the best of luck with my dates themselves.
Sometimes, you’re a young woman just navigating the dating scene. Other times, you’re an involuntarily appointed therapist for a lonely recent grad. Five minutes into our dinner, I knew the intricacies of his mommy issues. Ten minutes later, I downed my second glass of chardonnay. He was a sweetheart, though, and covered our check. Dinner with a therapist ought to cost $350.
Try again? Mr. CEO-of-Two-Companies-at-Twenty-Seven led me inside the Jersey restaurant that inspired “The Addams Family.” We flung flirty, feisty remarks over a candlelit four-course spread. Handsome, funny, and rich? Some things are too good to be true, and they were. After a third drink, he revealed his Trump-favoring voting history. Sigh.
While a first date definitely isn’t the place to dish out your grievances against your parents or liberal politics, I harnessed and grew my patience for many people with many issues. We all have baggage. While I don’t necessarily want to carry theirs, I could be the reason they felt a little lighter, even if for one night. Call it public service if it helps.
I’ve danced, too. Dating across the Atlantic deconstructed my Western normative dating standards. Is it really weird to bring a date, who you like, along with your friends, who you also like, to a fun night out? I’m thinking of the college student in Rome who introduced me to his friends, and off we went, tearing up dance floors across the city.
Carefree European dating enthralled me, so naturally, I adopted it. On my first date back in the States, I grabbed the hands of a digital nomad and took him dancing with me and my friends. It was a strange sight: a 6’2” white man towered over four ethnic women, each a foot shorter than him. And it was great.
Between gourmet dishes and tequila shots, I noted what I liked about the person in front of me — and what I absolutely did not. It shouldn’t be a laundry list, but knowing the type of care you desire is just as important as knowing the kind of care you offer. Sounds like research to me.
Somewhere along the road, I recentered the focus of my dates. Will they want to see me again? Turned into Do I want to see them again?
It comes, and then it goes
Not to be overly existential, but nothing lasts forever, and that’s especially true in the casual scene. But that doesn’t mean you can’t savor fleeting temporality.
Sometimes you’re grateful that it’s temporary. Let’s give a hand to the finance bro who thought the date was going better than it was. Instead of leaving like a sane person, I decided to concoct a horrible story to scare him away. For one night, I had schizophrenia. (Not my brightest moment, I know.) “Are you medicated?” he asked. “No, it makes the voices quieter,” I responded. He gave me a blank stare, and I thought I’d won. I did not. He was into it.
Other times, you fall a little harder than you mean to. I spent what were supposed to be my final two nights in Italy with blonde hair and blue eyes. (My ancestors are spitting at me, and my friends are in active pursuit of decolonizing me). I felt like I was on the edge of something new, and overwhelming emotion overrode all the analytical parts of my brain. To spend just a few more moments with him, I rescheduled my international flight. It was the riskiest decision I’ve ever taken, all for one more day of feeling. I don’t regret it at all.
Supposedly, we are meant to latch onto relationships. But learning to let go is a lesson in taking life as it comes and goes, savoring both sweet and sour. And I’m a connoisseur in letting my taste buds explore.
Graphic by Caroline Clark
There is solace in silence
So, you thought you had a good time, and your date seemed like they did too. Maybe they even told you they did. And then…silence. It hurts to be ghosted, and perhaps you channeled your frustration into crafting the perfect you-suck-and-let-me-tell-you-why text. But clicking send rarely helps more than not.
There is little payoff in manipulating meaning out of silence. Their ghostly nature need not materialize your greatest insecurities. It doesn’t mean they disliked how your eyes wrinkle when you smile, noticed the uneven curve of your hips, or were uninterested in your life — the one you’re still learning to call yours. Let the ghost pass through you and keep walking.
Consider, too, that while you’re waiting for a text back from Date #12, Date #7 is still waiting for yours. I had to gift myself the honesty of where I went wrong because I am no better than the person who, unexplained and unexpectedly, disappeared from my phone when I did the same to another. You can only sense inauthenticity in someone because it’s a reflection gazing back at you.
Vulnerability is tuition
Luckily or not, a series of bad dates makes the good ones that much better. A graphic designer introduced me to my top Spotify artist of 2023, and at his concert a few months later, I silently thanked the boy whose number I forgot to catch. The aforementioned digital nomad inspired me to spearhead my own adventures, and I have flights planned and booked across the world for the next year. As winter winds rattled his window, an artist held my gaze with a tenderness I remember with warmth.
If you’re in the casual scene, you probably won’t be scared to show a little skin. Don’t be afraid to show a little heart, either. It’s okay to lend a little part of yourself, even for a moment, even if you’re scared of how it’ll be touched, even if it’s to prove to yourself that you can. Sharing yourself doesn’t mean giving your whole self away. And if they return your softness a little bruised, thank them for the chance anyway. Vulnerability is the tuition I pay to grow stronger the skin and more secure the heart.
My casual dating era has come to an end for now. In its next season, I will continue to interpret dating as self-exploration, hopefully with more women (Ladies, my DMs are open year-round). In the meantime, I’ll encourage my fellow 20-somethings to embrace all the mess and charm of casual dating. I close this chapter of my life with great satisfaction. After all, I had a fuckload of fun. ■
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