OKBye Story #15: The Fault in Our Date

A year ago, I visited New York and fell in love (with the city, not with an actual person, obviously.)

New York was cold and ableist as fuck, but everything there was invigorating and exciting and things were always happening. Save for the freezing ass weather, it really did feel like a second home to me. I didn’t visit New York for the sole purpose of seeing the east coast, though. I went to visit one of my good friends, Shana, whom I had not seen in a long time.

Being the high-strung individual that I am, I demanded we have planning sessions in advance via Skype in order to map out the logistics of what we would do for the one week that I would be there. She complied.  After careful consideration and some half-assed research, we planned to visit at least one art museum, go to Times Square for New Year’s, eat a New York bagel, check out Chinatown, see an off-Broadway play, and…

“You should go on a date in New York!” Shana exclaimed.

I gave a dismissive laugh or something, then moved on to analyze the best building to get to the top of for that incredible view of the New York skyline.

I thought Shana was joking about going on a New York date, but she wasn’t. A couple of days after I arrived at the Big Apple, she brought it up again.

“Ugh, okay whatever,” I said, and changed the location of my OKCupid account to New York. Within the span of 24 hours, I had received 5-6 messages from a flock of horny East Coast dudes who were drawn to my self-deprecating, cynical slacktivist OKC profile. I skimmed through their messages, most of which were unappealing. But there was one that caught my attention:

RandomDude15 I’m jaded, but I still believe gender and sexuality are constructed, and fuck the police 24/7. Wanna kick it?

This response impressively managed to be informative, succinct, and straightforward all at once, which I greatly appreciated. I showed Shana, who weirdly oscillated between gushing excitement for me and extreme annoyance. “OH MY GOD! This isn’t fair! You’ve been in New York for like two days and you get a guy who actually sounds cool!” She went on to look at his pictures. “AND he’s hot! I hate you! I hate you! Oh my god, you have to meet up with him! And write my OKC profile for me! Oh my god!”

I looked at…uh, Jack’s profile. He was 29 years old and a 90-something percent match. And he was white. He had all the trappings of the kind of guy I was trying to avoid. He was hot though, in a douchey sort of way. I felt a weird mixture of flattery, irritation, intrigue, skepticism, and insecurity at the thought of a conventionally handsome grown man taking an interest in me, a scrawny and rather androgynous-looking 23-year-old Asian chick (still sporting the glasses-and-no-makeup look at the time, plus a super short haircut that was a former pixie awkwardly growing into a bob). “I don’t know…”


Shana was having a fit. No seriously. She was crying and laughing so hard that our fellow subway passengers were glancing our way. “I’m…I’m flustered,” she gasped out as she wiped away tears of…I don’t know what. (We’ve had many moments together like this, whether it was just one of us or both of us in hysterics, moments I consider to be the highest mark of friendship.)

“Meet up with him!” Shana kept insisting.

I thought about it. What was the point? I was only visiting New York for a week. I would never see this dude again. But then it dawned on me: maybe that was exactly the point. It’s not like I had seen any of the other guys ever again, and they had been local to me. The one-date deal was something I should totally be used to by now. So what could it hurt, having a New York date? It sounded like something a spontaneous and optimistic individual would do, and didn’t I want to pretend to be a spontaneous and optimistic individual?

But what would we do? What activity could we possibly undertake that would be so awesome and kickass that it wouldn’t matter if this guy wasn’t awesome and kickass?

That’s when it hit me.

CrumpleHSnorkack Let’s do karaoke
Sent from the OkCupid app Dec 30, 2014

RandomDude15 lol what
Sent from the OkCupid app Dec 30, 2014

RandomDude15 How’d you know I love karaoke
Sent from the OkCupid app Dec 30, 2014

RandomDude15 Are you free tonight? I just got flaked on by a Tinder date 😀
Sent from the OkCupid app Dec 30, 2014

Tonight?! I was thrown off by his genuine spontaneity. (And his blunt admission of trying to hook up with other girls and failing at it, thereby making me his Plan B. In any other instance I would have been turned off, but given the circumstances, I let it pass.)

“He wants to meet up tonight,” I said to Shana, horrified. We were on the subway, having just gotten back from viewing the Statue of Liberty via ferry.

“Ask him if he’s free tomorrow for New Year’s,” Shana suggested. “Maybe he can party with us after midnight.”

He wasn’t free tomorrow.

Goddamnit. So it was now or never. I looked down at my outfit. I was actually being a sensible person for once and had dressed for comfort, not style, which meant a baggy sweater, heavy jacket, jeans, and a pair of childish-looking furry boots. I did not look like date-with-a-29-year-old material. Ugh.

“Could we take the train back to your place so I can change?” I asked hopefully.

Shana shook her head. “It would take too long. We’d miss out on Chinatown and Little Italy.”

I sighed.

Quit being so fixated on your appearance, a voice in my head criticized. Who the hell cares if you’re not dressed up? It’s this dude’s fault for being all spontaneous and last minute and shit. If he wanted you to look good he should have asked you in advance. Also, you are definitely never going to see him again, so dressing to impress is pretty pointless when you guys don’t have a future together. Stop being insecure and superficial, your internalized racism/sexism is showing and I think you–


So with my zero-fucks-given attitude and Shana as my unwanted cheerleader, I made late night plans to do karaoke with Jack at some lounge Shana had recommended. I wondered if I was going to regret this. I usually did. It’s not about him, I reminded myself. It’s about karaoke. Which was totally going to be awesome.

Although I understood that there was no future with Jack, I still wanted to look somewhat presentable. The headband I had been wearing all day had given me a really bad case of headband hair, which can happen if your hair is as thin and oil-prone as mine.  So when Shana and I ended up at a crowded Chinese restaurant for dinner, I excused myself to use the single stall bathroom, where I immediately began splashing my face and my hair with water. Then, using a travel size brush I had purchased at the convenience store, I attempted to smooth out my wet strands of hair while drying myself off with paper towels.


This was a rather long process. There was a lot of knocking at the door. Whoever was waiting to use the bathroom was getting really impatient. Ok, ok. I opened the door. The middle-aged Asian man waiting outside found himself staring at an awkwardly smiling, soaking wet prepubescent Asian Daniel Radcliffe who skirted around him to make her way back to the table where her friend was sitting and probably still sulking over the fact that the waiter had given her the “white people” menu.

“Wow, you look like you just showered,” Shana commented.



“So, I’ll text you when I’m done?” I asked.

Shana and I were just outside the karaoke lounge, saying our goodbyes-for-now. I suddenly felt awful and antifeminist for leaving her just so I could meet up with some dude. I briefly considered having her be the third wheel, like she had requested of me all those times back in college. Nah, that would be way more awkward. Anyway, this was all Shana’s idea and I was pretty sure I wouldn’t be hanging out with this guy for very long.

Shana nodded. “Let me know how it goes!” We then parted ways: she to a random bar, and me up the stairs and into the lounge.

I requested one of the smaller rooms to rent and found myself sitting alone in the semi-darkness. Jack had texted that he was going to be a little late and I didn’t care. Not with a mic, sound system, and thousands of instrumental songs at my disposal.

What should I sing? I went with the obvious choice and tried doing “Empire State of Mind” by Jay-Z and Alicia Keys. “New Yoooooooooork….yeah, uh huh uh huh uh huh…” God, I sounded terrible. I couldn’t imitate Jay Z’s rap style or hit Alicia Keys’ high notes. Oh well. At least no one was around to witness my fail. Halfway through the song I gave up. That was when Jack showed up.

He was a little bit different from what I expected. Somewhat shorter. Bigger head. A strong accent that was the opposite of sexy. (I wasn’t sure what it was. It sounded like the stereotypical Jersey accent my 8th grade history teacher would put on for cheap laughs.) He was still handsome enough to make me nervous, though. (Picture a less hot version of Adam Levine.)

Jack gave me a hug. “Already getting started?”

“Yeah….I’m gonna do a different song.” I grabbed the…um, karaoke controller to input a favorite, “Super Bass” by Nicki Minaj. I’ve done this song a hundred times by now, and it’s consistently been a hit with people, probably because seeing a scrawny Asian girl rapping, “Yes you get slapped if you lookin’ ho” provides some pleasantly surprising entertainment.

Jack was fairly impressed. “Nice.”

“Thanks. What are you thinking of singing?” I asked.

He began rattling off the names of rap songs and artists that I had never heard of in my life. Must be the age difference. I politely smiled and nodded in response. 

We took turns performing. He was actually a pretty good rapper himself. I strained my ears and tried to catch him slipping up and saying the ‘N’ word, but from what I could gather, the slur never left his lips. Okay good.

While Jack kept doing obscure rap music, I kept singing really cheesy pop songs. At some point I became acutely aware of the overtly sexual lyrics of all my song choices. God. Why hadn’t I noticed how sexual they were before? I wondered as I self-consciously sang “Closer” by Tegan and Sara:

All you think of lately is getting underneath me
All I dream of lately is how to get you underneath me…”

Fuck, does he think I’m singing to him? That I picked this song to not-so-subtly let him know that I wanted him underneath me, when in reality I was leaning towards the side of “nope, definitely not”? (His bad breath was cancelling out his fairly good looks.) It’s just a song though! Right?! I was afraid to look at him, and instead kept my eyes trained on the screen.


I suggested we switch things up and do a song together. He was game. We did an enthusiastic rendition of a Backstreet Boys song. (Probably “I Want It That Way.”) I was totally down to sing 90s pop music all night, but Jack for whatever reason wanted to take a break and have an actual conversation so he could get to know me, or whatever.

I told him I hailed from California and was only visiting New York for the holidays. He seemed to take that news pretty well. He told me there was a small Southeast Asian community in the Bronx, which he knew about because of the immigrant rights group he organized with.

Okay, you’re probably gonna judge me for this next part. I wasn’t totally clear on what he meant by “organize.” (I don’t know all the functions involved with social justice work, okay–I’m just a slacktivist! Leave me alone!)

“What do you mean you’re an ‘organizer’?” I asked.

“You know, I help out with the cause,” he replied very vaguely and unhelpfully.

“Well…what do you organize?”

“Whatever needs to be done. Like putting on events, or promoting stuff.”


The next half hour or so was spent discussing white privilege. “My people are treacherous,” he kept saying, which I found kind of funny because it brought to mind a mental picture of white people as pirates saying “Arghh!” which, I mean, is probably also historically accurate.

“How do you be an ally without letting your white guilt get in the way?” I inquired.

“I don’t have any guilt,” he answered.

“Do you think it’s racist when white people prefer dating other white people? I had this argument with some other white guy. I think it’s racist.”

“Nah,” he said, annoying me. “If you grow up in an all white community, of course you’re gonna have a preference for white people.”

“But–that’s racist!” I spluttered.

“It’s not something you can control, your dating preference. I have a friend who also does social justice organizing. Said he could never be with anyone other than a white girl. That’s just what he grew up with. What he’s used to. What’s he gonna do, try to find himself a black girl to prove he’s not racist?”

“Hmm.” Jack’s argument was kind of convincing me to see the point that Colin had been trying to make (See OKBye Story #13: When Awkward Met Awkward). In the moment, anyway. I now still think it’s racist to have a racial dating preference, especially if you’re white (exception includes any person of color trying to preserve their cultural heritage).   Race is a social construct, people! No race of people looks one type of way or acts a certain way. No racial group is a monolith, no matter what white people would like you to think. If you find yourself falling for the same race over and over again without consideration of anyone else you better think long and hard about why that is. Just because you can’t really control your racial bias doesn’t mean it isn’t a problem. I’m just saying, fall in love with people without bringing your fucked up preconceived ideas of who they are, and what others are not, into it.

Anyway, it was getting kinda late and I didn’t want to be charged for yet another hour for the room if we weren’t going to be singing, so I suggested we head out. We ended up splitting the bill, which was cool. As we left the lounge, I started feeling nervous. As I’ve said before, I think the goodbye is the worst part of any date.

“So…I have to meet up with a friend…” Ugh. It sounded like I was lying, which I was not. Shana was waiting for me who-knows-where and I had to return to her to mitigate the irrational guilt I was feeling. “Where are you headed?”

“I don’t know,” he said. “I’ll figure it out.”

“It was nice meeting you,” I said. We were at the curb. I was hoping he would just go away.

“Yeah.” Jack grinned and walked the other way.

Whew. I texted Shana, asking where she was. As I was waiting for her to respond, I saw that Jack was coming back my way again. Goddamnit, the awkward see-you-again-even-though-we-already-said-bye scenario.


I put on a smile as he got closer.

“Went the wrong way?” I said lightly.

He laughed, then gave me a hug. Like, a forreal hug. He even buried his face into my shoulder. I held still, feeling somewhat weirded out. Then he was gone.


A few days later, Shana and I were planning an impromptu hotel party/fake wedding to celebrate our homosocial love. I invited 5 different OKCupid dudes in the area who had messaged me and didn’t seem like serial killers, because the more the merrier, right? One of them being Jack. He said he had gotten sick but would try to make it.

On the day of the party, we had a text exchange that went something like this:

Me: Hey are you still down to come to our party? It’s at 7.

Him: Can’t. Too sick. Coughing up phlegm

Me: Ew. Okay well, hope you feel better. It was really nice meeting you! You’re a pretty cool guy.

Him: I thought you didn’t like me lol

Me: Lol I just come off like a bitch when I don’t know people. Didn’t you read my profile?

Him: Thought you were joking. You were a 90 something match and the girls I match up with at 90 have radical politics and are DTF

Wait, WHAT?

DTF? As in Down To Fuck? Was he trying to say he thought I was down to fuck?

Me: Hahaha uh well I don’t think we’d be sexually compatible anyway

Him: Yeah sure lol

Wait a minute.

Was it possible that I could have actually gotten laid that night, had I quit with the resting bitchvibe and had he popped a mint?

Oh, well. I wouldn’t want my first time to be with some smug Adam Levine lookalike I would never see again anyway. Maybe for my fourth or fifth time (provided he brush his teeth), but definitely not my first.

Yeah that’s right, I said my first time.

If you don’t know me very well (or haven’t been keeping up with my blog), you might be gasping: Learkana, you were a 23-year-old virgin at this point in time? 

Oh, shut up.

The party was a blast (except for the part when it ended early because the hotel threatened to call the cops–not that exciting of a story), New York was a blast, and no, I didn’t get laid or fall in love with a tall, dark, and handsome New Yorker. However, I did end up crushing really hard on the short, dark, and handsome Californian I had already scheduled a date with the night after I got back from New York–which is another story for another time.

tl;dr New Yorker boy messages Californian girl who is just visiting, girl and boy meet up to sing karaoke and talk about white privilege, girl is cold and detached as defense mechanism against boy’s good looks and age, girl and boy never see or hear from each other again

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