OKBye Story #13: When Awkward Met Awkward

Doesn’t dating a white guy mean betraying my sociopolitical values as an intersectional feminist?

A couple of years ago, I posed this question to my ethnic studies professor. She said, “Well, dating men of color isn’t any better. You still have to deal with the gender aspect of it, which is fucked. If you really want to be political about dating, you would only date Asian women.”

“Oh.” I didn’t have the guts to be that radical. I had no burning desire to veer from the boring, normalized path of heterosexuality, so I decided that having a white guy as a boyfriend wouldn’t be the worst thing in the world, if it happened.

So when Colin (name changed to protect the oblivious) messaged me on that arbitrary day at the end of last September, I was excited. Sure, his profile was kind of boring in a white dude way (carefully constructed sentences devoid of emotion or personality, painfully specific lists of obscure music and books, shitty “most private thing I’m willing to admit,” etc.), but he looked cute and dressed well and also, we had a high match percentage! (I don’t understand myself. I really don’t.)

And the message itself! A first message meant everything to me. I usually ignored generic greetings (“hey how’s it going”), negging (“you seem like you’re high maintenance”), unoriginal compliments (“I love your smile :)”), long rambling paragraphs that tried too hard to impress (“I noticed in your profile that you blah blah blah which is so cool because I blah blah blah blah blah blah blah”), and of course, downright creepy messages (“I’m stalking you via my astral body” –actual thing written to me). However good a dude may have looked in his pictures, and however witty he may have sounded in his profile, it’s what he wrote to me that was the deciding factor to whether I responded.

Anyway, I’m probably building this up to be way better than it is, but here is Colin’s first message to me:

RandomDude13 Man, the implications of “liking” someone’s profile are a total mystery to me. Actually there is nothing about OKC sociology that I feel I even vaguely understand. That’s why when I read someone’s profile and they seem cool/interesting/reasonable, I immediately message them the first fucking thing that comes into my head before I can start overthinking it.

I don’t get a lot of return responses.


Sent 9/27/2014

Colin’s message was honest and endearing–in an awkward, neurotic, self-deprecating sort of way. (Now I’m realizing I liked the message because it reminded me of me. Such a narcissist.) Regardless, I was immediately compelled to respond.

But not before my friend Elizabeth texted me, “Hey! Did RandomDude13 message you on OKC?”

Wait, what the hell? How would my friend in real life know about an online stranger who had just messaged me? Unless she had used her own OKC account to…oh no. Oh no. OH NO.

I texted Elizabeth something to the effect of, “OMG PLEASE TELL ME YOU DID NOT TELL HIM TO MESSAGE ME!!!111”

To which she responded with something like, “I did! He came up in my matches and I thought he would be perfect for you because he has an English degree like you and mentions gender in his profile!”


To which she responded: “I just gave him your username and told him to message you, kbye. Talk to him!!”

This bitchhh. What kind of person tries to play matchmaker on a matchmaking site? The kind of person who would do a jogathan with me in high school while asking every boy who overlapped us if he wanted my hand in marriage, that’s who. (Yes, that happened. And obviously, all I got out of that was blank stares and humiliation. Thanks Elizabeth.)

In about an hour or so I got over the weirdness of it all and replied to Colin.

CrumpleHSnorkack Hahaha. Hi! Yeah that’s pretty much my understanding of this site, too. Also my friend is such a busybody lol

Sent 9/27/2014

Okay, not very witty, but probably one of the more friendlier responses I’ve given to a guy.

The conversation continued:

CrumpleHSnorkack Did you get your degree in English or did she just make that up? 

RandomDude13 Yeah that’s the first time someone’s ever messaged me telling me to message someone else. So new experiences I guess.

I did actually get a degree in English, but that doesn’t necessarily mean the rest of what she said was true. Were you an English major also? 

CrumpleHSnorkack All she said was that we would probably get along and have a half-decent conversation, lol. Ah, I see it on  your profile now. Yep, English major too, with a creative writing emphasis. Where’d you go to school? 

RandomDude13 San Jose State University, where I was, er, an English major with a creative writing emphasis. There was no straight creative writing major. You’re not about to tell me you also went to SJSU, right? Because I have a terrible fear of coincidences. 


The conversation went on. And on. And on. And on. I found myself genuinely enjoying talking to Colin. He was silly and witty and smart, plus he seemed to be aware of his white male privilege (this I noted after some sporadic interrogation). Most importantly, he messaged me just as quickly as I messaged him, which indicated he actually took an interest in getting to know me and what I had to say. I soon got it into my head that having my friend play Cupid on OKCupid was the best idea ever.

Such a naive fool I was.

I’m getting ahead of myself, though.

At some point, I asked Colin for his number, and we started texting nonstop. We talked about how awkward we were, and left each other awkward voicemails just for the hell of it. (I was amused by how much he sounded like a 1920s newsie.) We talked about gender roles. I suggested we meet up with him wearing a skirt and me wearing a tie, but he declined, not because of some notion of masculinity he personally wanted to uphold, but because he feared being harassed publicly by femmephobic strangers (which was a valid concern). We talked about the highs and lows of our nonprofit administration jobs: he worked at some organization in SF that did stats on workplace safety, and I was pushing paper for the anti-trafficking cause in Oakland. (Still doing that, but whatever.) I started to really like him.

However, I knew that liking him solely based on the text messages we were exchanging was stupid, and unfortunately, I knew this from past experience. So a few weeks into our, uh, textship, I pushed for us to meet in person. He agreed, both of us knowing (and articulating to the other) that we were expecting the worst, but that was okay and also weirdly reassuring.

Colin and I decided to get drinks at a bar in downtown that one of us had stumbled across on Yelp and the other had deemed acceptable. (Clearly, neither of us were Oakland natives, nor people who went out much.)

In person, he not only sounded like a 1920s newsie, he also looked like a 1920s newsie, with his little cap and fancy vest and dress shoes. Not that I minded. I was more bothered by how skinny he was, like I could easily break him if I wanted. (As mentioned in previous stories, I have a thing about guys being just as scrawny/even scrawnier than me. Not a dealbreaker necessarily but definitely a turnoff.) But of course, I wasn’t going to body shame him right then and there, I’m not that much of an asshole, okay. We stiffly hugged each other and went inside.

The bar wasn’t too crowded, which was nice because we didn’t have too much trouble hearing ourselves talk. What wasn’t as nice was the spurts of conversation that would trail off into silence. It was just as we had expected/verbalized to each other: in person interaction was weird and uncomfortable and anxiety-inducing. What was once a wavering ellipsis on my iPhone was now a pair of eyes staring intently at me.


I decided we needed a distraction from ourselves, and suggested we play “Never Have I Ever.”

Colin was down to play. The game ended up running for at least a couple of hours. I don’t remember much of what was said. I vaguely recall starting out with cheap shots: “Never have I ever had a dick. Never have I ever gone to a coed college. Never have I ever had white privilege.”

I was on my third drink and regretting it. The nausea was already kicking in. (Ugh. I’m such a fucking lightweight. Also possibly allergic to alcohol.) I coaxed Colin into drinking some of my beer so it wouldn’t go to waste, but he was a lightweight too and said he couldn’t finish it. One of us suggested we take a walk. One of us said yes. We both got up and left the warmth of the bar for the brisk night air.

We ended up walking along Lake Merritt. In my slightly tipsy state, I felt completely comfortable with Colin. At some point we took a break, sat down and looked at each other.

“This is very awkward,” he said suddenly.

“Really?” I said back. “Why? I feel totally fine.”

“I don’t know.” His brow was crinkled.

I wondered if it was because he was feeling some sexual tension I wasn’t. I decided (in alignment with my better judgment for once) that I wouldn’t bring it up. Instead, I suggested we walk back.

He ended up walking me to my car. I think we probably did the awkward hug thing again. As I got into my car, he bowed and left. I laughed aloud. Did this motherfucker just bow to me? (He mentioned he would do it through text for reasons I can’t remember.)

I drove home, not sure how I felt about him, or how things were unfolding.

We resumed texting and suddenly it felt like nothing had changed from before we met. As if our first date was just a bump in the road and now we were back to cruising along, using our English degrees to crack grammatically correct, rhetorical jokes and texting each other strings of emojis for the other to interpret (of course, I was the one who got him hooked on emojis).

I told him about getting a short story of mine published in an anthology. He actually bought a copy of it and read my story, which I hadn’t anticipated. I texted him that this was awkward. He texted does that mean I didn’t want to know what he thought of it. I texted ugh ok what did you think of it. He texted me the kind of unintentionally condescending review that of course a white dude with an English degree would give. Said he enjoyed it for the most part, appreciated the biblical pastiche, there was just that one thing that was lacking, but there were a few other things that compensated for it, blah blah blah. Something pretentious like that.

Out of pettiness and spite, I demanded to see an excerpt of his writing. He complied and emailed me a few pages of his unpublished superhero novel. It wasn’t very good, I thought with a sort of sick and twisted triumph. It was a bunch of fancy words stacked on top of each other like cardboard boxes with nothing inside them. The characters all had the voice of an old white dude. It was boring. It was mediocre. It was pointless.

I didn’t say any of that. (Again, I’m not a total asshole, just maybe like 3/4ths of an asshole.) I made a few vague, intentionally condescending comments and left it at that.

Well, mostly. This was just one example of what also became of great concern to me: his well-to-do white maleness. (An issue that also came up in OKBye Story #7: He’s All That.)  While I liked talking to Colin, I felt like I could only really show one side of me when I interacted with him: the whitewashed side. The truth was, I didn’t speak in perfect Standard American English all the goddamn time. I wasn’t always pseudo-witty and composed. And I would rather shake my ass to Beyonce in the club than go to the concert of some obscure indie band just to passively nod my head along. More importantly, I couldn’t imagine him meeting my family or me meeting his friends. Wasn’t that a bad sign?

Well, it’s too soon to tell, I rationalized. We had only met up once, after all. So I asked him if he wanted to get boba with me. (In Berkeley. No way was I taking him to my favorite place in Oakland.) Colin said sure, and admitted he had never tried boba before. Big surprise.

We met up at Sweetheart Cafe on a late Saturday afternoon, ordered separately, and sat down at a table together. I watched him very closely as he was about to take a sip of his first ever boba tea drink.

“You seem very intense about this,” he said, raising his eyebrows.

“I am. Drink it,” I ordered.

He took a sip. “This is pretty good.”

I suggested we walk around so we wouldn’t have to sit and stare at each other’s faces. Walking made things a little less awkward, but not really. I couldn’t help but be hyperaware of how we looked: an Asian female with a white male, your typical Berkeley interracial couple. Ugh.

We aimlessly chattered as we walked. Or well, we tried to. More lapses into silence.


When I pressed him to speak on the subject of racism, he said he would rather not talk about it at the moment.

Damn these dudes and their refusal to talk about social justice issues! I thought, annoyed.

Well, you are on a date, another voice inside my head countered. Social justice is important and all, but you can’t deny it’s a boner shrinking topic.

Okay whatever.

I asked Colin what he had thought about the boba itself. He said it was just okay.

I decided this date was not going well.

To make matters worse, we had somehow veered towards talking about how awkward we were being and how we seemed to have run out of things to say to each other. (Which kind of happened in OKBye Story #12: Bitch in Berkeley, but hey, this time it wasn’t just me. For some reason, I still hadn’t gotten it into my head that being meta was pretty much ruining everything.)

I did try to salvage the situation by going on a tangent about how chemistry wasn’t that important and that it was a gradual process, getting comfortable with someone you didn’t know very well.  He listened and said he agreed. But did he really believe in what I was saying? Did I believe in what I was saying? Looking back, it seemed we were just trying to convince ourselves of something that wasn’t true–a misguided attempt to sidestep the inevitable.

I offered to walk Colin to his car this time. As we waited at the curb for the walk sign to flash, I blurted out, “So…what’s happening? Are we going to never see each other again or…?”

“Is that what you want?” he asked.

“Well, it’s not that.” I backtracked. “It’s just…I’ve never gone on more than two dates with a guy.”

“So history is not on our side.” He considered this. “Well, I’d like to see you again. Because I like you.” He looked straight at me as he said this.

“Oh. Okay,” I mumbled. (Yes, that was my shitty response.)

The walk signal lit up and we crossed the street. When we reached the parking garage where his car was, we did an awkward hug thing again. My face ended up getting crushed into his shoulder.

“Quit being so tall,” I mumbled some more, and left.

At home, I turned his words over in my mind: I like you. He was only the second guy to ever say that to me.  (The first one being some boy in Kentucky who fell in love with the sight of me passed out on his couch at 5am wearing a shirt that read “vagina” across the front. But I digress.)

I like you. It’s kind of a brave thing to say in this fucked up millenial dating world. I admired Colin for saying it. I was flattered that he said it. What I should have said in return was, “I like you too.” But I didn’t say that. Why didn’t I say that?

Because I didn’t really know if I actually liked him. Ugh.

Why was this always happening? I was in a constant state of uncertainty when it came to these dudes. Not once have I ever thought, yes. This is it. This is exactly it. This is what I want. I started to wonder if there was something wrong with me.

The fact that I enjoyed texting Colin much more than I enjoyed his actual company also still bothered me. I suspected it had to do with Colin being more awkward in person than I was, which had never happened to me before–usually I took first place in social ineptitude. I guess I should have empathized, but c’mon! We couldn’t bond over awkwardness forever. Besides, he was older than me! He supposedly had actual romantic and sexual experience! What the hell was he doing, acting all nervous and perplexed and uncomfortable around me?

It’s only been two dates, I reminded myself. Things would get better. I hoped.

We kept texting. Colin invited me to see a play with him. I declined. It didn’t sounded interesting to me, and as shitty as it sounds, I guess I didn’t like him enough to pretend to take interest.

Around this time, a lot of racial unrest was brewing, on- and offline. Of course, racial unrest is always happening, but it seems to hit its peak during the holiday season. There were multiple demonstrations in the streets of Oakland and the larger Bay Area, in protest of police brutality and the systemic killing of black people. (I joined in on one, only to later regret it when I found out it had been organized by a shady cultlike socialist group who had a different agenda in mind. Oops. Social justice faux pas. But I digress.)

The racially charged atmosphere got me thinking about the root cause of it: white supremacy. I felt angry, sad, frustrated, and helpless, trying to figure out what part I could play that would have any meaningful impact on the destruction of racism as a system of oppression. And while it may sound unfair, thinking about these things made me resent Colin and his whiteness. Sure, he acknowledged that racism existed, would never call someone the N word, probably never voted Republican–in other words, met the basic requirements of human decency. And obviously, Colin wasn’t personally at fault for institutional racism. But what was he doing with his white privilege, other than exercising it to his own advantage 24/7?

I bet his best friends were all white. I bet the subject of racism never came up, except at awkward Thanksgiving family dinners when his bigoted uncle or whoever came over and said racist shit and Colin wouldn’t say anything because he’s too passive and non-confrontational. I bet he was going to live all 26 years and counting of his life breezing by on his white privilege, blissfully complicit and only socially aware through a lens of detached self-interest. In the meantime, black people were dying in the streets.


These internal struggles caused me to bring up a question I had chosen to stifle the first time I looked through his OKC profile. One of the questions he answered concerned race. I think it went something like, “Is it okay to prefer dating your own race?”

He had answered yes, with the explanation that “positive bias” (e.g. “I prefer to date Caucasians [his word choice, not mine]”) is okay, whereas “negative bias” (e.g., “I do not want to date black people”) is not okay.

It sounded a lot like fancy white people talk excusing white people fuckery to me, but I let it slide initially because I figured he was just being an optimist who happened to be white. Now with the threat of white supremacy lingering on my mind, I texted him about the elephant in the iMessage thread: racism.

The conversation did not go very well.

I can’t recall the exact words that were said, but our little chat went something like this:

Me: Hey, this is random but I remember you answering a question about racial dating preferences on OKC. You said positive bias is okay but not negative…idk can you clarify that for me?

Him: Hmm, I don’t remember exactly how I answered but yes, I would say that having a preference isn’t an issue so as long as someone isn’t excluding a particular race.

Me: Uhhh well I would say having a racial preference is racist. Like, I would understand for people of color in terms of wanting to preserve their culture/heritage as racial minorities, but like for white people to prefer other white people…that’s pretty white supremacist

Him: Well, statistically speaking, most people date within their race. I would not assume someone is racist simply because they prefer dating someone within their own race. Often, this isn’t something conscious.  And people usually go with what they are familiar with.

Me: Well it doesn’t have to be mutually exclusive. People can be racist and also want to date who feels familiar.

Him: I didn’t say it was mutually exclusive.

Me: Well whatever, you implied it. I’m just saying, everyone is racist.

Him: I refuse to automatically assume everyone is racist by default, that is completely ridiculous.

Me: Well that’s easy for you to say, you’re a white dude

Him: I don’t think continuing this discussion is productive. Good night.

I didn’t respond. I was too pissed at his pretentious white pseudo-progressive rebuttals.

A couple of days passed. A week. Several weeks. I didn’t hear from Colin again. I realized after the first week I would never hear from or see him again, and that I was perfectly okay with that.

What a waste of time, I thought. Oh well. At least I got a book sale out of it.

Once unsure, I now knew for certain: Colin was not what I was looking for.

He was an ideal I had clung to in the past: a nerdy white boy I could exchange witty banter and affirm my normalcy with. But Colin was my last straw on the matter: I could never seriously be with a white guy. On a fundamental level, he would never understand me as a woman of color, especially as a socially aware woman of color who wasn’t afraid to speak her mind. His privilege would always get in between us.

So fuck what my ethnic studies professor said: I couldn’t stop being straight, but I could certainly stop seeing white dudes. No more white dudes for this raging intersectional feminist of color!

Ah, shit.

My dating pool just got a lot smaller.

tl;dr Boy messages girl because girl’s friend told him to, girl and boy have an incredibly drawn out grammatically correct emoji-filled textship, girl and boy meet and it’s awkward, girl and boy keep texting each other, girl and boy meet again and it’s still awkward, girl gets fed up with white supremacy and takes it out on boy, girl and boy never see or text each other again

2 thoughts on “OKBye Story #13: When Awkward Met Awkward

  1. Pingback: OKBye Story #14: Friends with No Benefits | lampshade on her head

  2. Pingback: OKBye Story #15: The Fault in Our Date | lampshade on her head

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