My First Date Ever: Expectation vs. Reality

The first date I ever went on was thanks to OkCupid. I was twenty-five and new to the world of dating, not just online dating. I had just graduated, was living at home with my parents and had landed my first job at a company that made aerospace transparencies – a fancy phrase for “airplane windows.”

The job paid fifteen dollars an hour and was, up to that point, my biggest paycheck ever (if I adjust for inflation, most jobs I’ve had since then actually pay about the same…and…sad face). Laugh all you want, but it was quite enough discretionary income for a young woman who lived rent free and had no car payments (Thanks Mom and Dad!) Or any payments really, except for my monthly credit card bill which listed nights out with friends, gas, clothes, shoes and the occasional tub of greek yogurt from Trader Joe’s.

Which made me feel, in one way or other, ready to start dating. I figured since I had a job, I could date guys with jobs (Yeah! Standards!) and be able to pay for the occasional dinner and movie tickets and not have to think “Thanks Mom and Dad!”

So my first date. I don’t remember his name, but I’ll call him Steve. Steve and I emailed for a week or so – long pointless emails I thought meant we were “getting to know each other” – a rookie mistake, but it took like three more guys before I learned to save time and keep these messages short – before he suggested we meet up for dinner.

“Sure,” I said and, thinking with more excitement than was due, This is going to be my first date!

I found Steve as well as our email banter attractive. He was a lanky, twenty-seven year old nerdy-ish Chinese guy who worked in IT – whatever that meant – and had a snarky sense of humor. Check, check and check. One of his profile photos was of him smiling goofily next to a chalkboard with a bunch of numbers and charts on it and I, like Groucho Marx, thought, “He wasn’t an English major. Good.”

Steve lived about an hour away and suggested a place thirty minutes between our two houses, in the city of Rowland Heights.

“You like Taiwanese food?” he asked.

I said yes. Over our first few messages, we had “clicked” over the fact that while technically we were Taiwanese (I was born in Taipei) we told people we were Chinese because ethnically, we were. And in general, I did not make a big stink about it but found it irritating when super Taiwanese people got in my face and called me a Communist for saying so.

“You’re not born into the Communist party,” a Chinese person from China once said airily to me, “You have to be invited.”

I’m still waiting for my invitation.

“So am I,” Steve had said. We had a good laugh over the OkCupid chat service.

Steve suggested Class 302, a Taiwanese cafe that served street-food-type things like minced pork rice, fried pork chops over rice, stinky tofu, and stir fried veggies, along with tapioca drinks and shaved ice. It was opened by a guy from Taiwan and popular with the AzN teens, FOBs and minivan driving Chinese moms of Rowland because a.) the food is pretty good and reminiscent of home and b.) it’s cheap, which means you won’t break the bank if you eat there on the regular.

I had never been and had no idea what the price point was, but thought, “Whatever, this guy seems cool and I trust his choices.”

I dressed carefully for the date, much like I did in college before I went to stalk my Slavic Lit professor’s office hours (sadly, the bulk of my romantic activity in college), choosing a silk cream shirt, skinny green pants and gold flats. He had listed his height as 5’10, but I had heard from my more experienced peers that this, alongside income, was the thing guys enhanced the most in their dating profiles. I did not want to stomp in and discover I was a giraffe to his prairie dog. I even put on makeup with a shaky but improving hand. To be honest, I didn’t need much at the time (smug smile).

Before heading out, I told my father where I was going. He asked for Steve’s phone number, in case the gentleman turned out to be a psycho-killer.

“I doubt he’d pick up if he kills me,” I said, but wrote it down anyway, smiling; I had never seen my dad be anything remotely resembling protective.

“Where’s he taking you?” my dad asked.

I told him and my father made a face.

“You’re driving all the way to Rowland Heights to eat there?” 

“We’re meeting in the middle,” I said, “He lives in Alhambra.”

“Alhambra’s far,” my dad said, wrinkling his nose. I could tell he was judging the Alhambra address. My parents worked hard to make sure we lived in a neighborhood with just a sprinkling of Asians. People in Alhambra, successful as they may be, might own a chain of laundromats rather than, say, real estate in slummy cities, as my father did. But before he could say anything else to put a damper on my date, I asked him what was the matter with Class 302.

He shrugged, “That’s more like a takeout place than a restaurant. You’ll finish eating in less than the time it took you to drive out there.”

Disdainful as my father was, I knew he knew his stuff. He often drove to Rowland, Hacienda, and Arcadia to eat with friends because the offerings for Chinese food were better. When we were younger it killed me that my dad thought it was worth it to drive an hour to get good lobster in a rundown restaurant whose dinginess always undercut the word “Palace” inevitably in its name, but as I got older I appreciated his wanting his friends, our relatives, everyone he knew basically, to share in these gustatory delights.

He knew which places were worth the drive. Apparently Class 302 was not. I began to sense the perils of trying to meet my parent’s still quite mysterious standards, vs. my own expectations, at the time equally murky.

But I was running late and besides, I said, “I don’t eat as fast as you do. And it’s expensive nowadays for young people to be dating. I haven’t even met the guy I’m not going to expect him to take me somewhere super nice.”

“Okay okay,” my dad said, “Go and have a good time.”

Though I should have anticipated otherwise because right before I pressed open the garage door, I could still hear my dad muttering and probably shaking his head, “Class 302, really?”


A few months prior to that first date, I was both encouraged to and prepared for online dating by my cousin D who at the time, had just turned 34 and was newly single. He was a good looking guy who never had any problem getting girls, but wanted to have more agency in his love life. Apparently this is a problem exclusive to attractive people: where ripe fruit keeps falling on top of their heads instead of them having to reach up and pick anything themselves. I’m sure it gets so annoying.

He nurtured his agency by signing up, simultaneously, for all the major sites available at the time: OkCupid, Match, and eHarmony. Tindr was just an embryo.

“Cupid’s free,” he said, when I mentioned I was ready to start dating, “And you’re young. You’re what – twenty-two?”

“Twenty five,” I said.

“That’s the perfect time for women to go online,” he said and unabashedly revealed that while the filter he set his age range to was from 24-34 (though later he admitted to be messaging a 22 year old girl), he mostly breezed over the profiles of women thirty and above unless they reached out to message him, which was quite often.

“But I’ve learned that the older they are, the more baggage they have.”


“Get on there while you’re young. Right now, you’re the one with lots of options and zero baggage” he took a step back said with well-intentioned urgency, “Seriously, don’t waste time.”

He went on to tell me one horror story after another about encounters with females aged thirty and beyond. More than a handful of women had posted photos from more than five years ago so that when they showed up my cousin hardly recognized them.

One woman showed up with a shock of white hair covering her face, which was far saggier than it had been in any of her profile photos.

“She kept pushing the white hair back behind her ears, as though I didn’t notice, but Jesus, just be up front!”

Worse, a few, while not so much aged, had gained more than ten to fifteen pounds.

At the time I sympathized with the women.

“Would you have gone out with them if they’d posted photos of what they actually looked like?”

“Probably not,” my cousin said, “But they shouldn’t have lied.”

“That’s not lying,” I scoffed, still thinking him unfair to write someone off for the way they looked. Or the way they looked now.

“Yeah it is,” he said, “Your profile is supposed to represent you as you are. It’s already hard enough to make anything out of the stuff you write, so the most you can do is make sure your photos are accurate. It’s the same if I lied about my height or my income or my weight. You think any of the women would have clicked on me if I looked old or ugly or didn’t say I worked where I do? Or if I did put those things and they showed up and I looked totally different and was actually broke? You think they’d want to go on a second date with me? No! They’d think I was a liar too and wasting their time!”

I had to agree. She probably would not have. I certainly wouldn’t. But I naively thought that since I had this conversation with my cousin, a seasoned online dater who also happened to be a man, the problems he encountered were probably more common to men.

It didn’t take long to find that this was common to both men and women.. A few months later I found myself driving to Class 302 for my very first date where I’d learn that all people lied about all the same things, just in varying degrees.

Click here for Part II

2 thoughts on “My First Date Ever: Expectation vs. Reality

  1. […] I didn’t date until I was 25, mostly because my years before were filled with crushes on celebrities and fictional characters ranging from Edward Norton to Anime cartoons. I’ve come a long way…I think, except for the moments during certain arguments with Tom, when I backtrack and think, “If Tom and I are meant for each other, why are we having another argument about _(insert topic here, involving anything from domestic inanities to personal values).” […]

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