I Went on a Date With a Suspected Republican

His name was Dan* and he worked in finance for a startup because this is New York. While I usually go for the charter school teacher types, he messaged me on Okcupid, asked me out for BBQ, he was cute, and beggars can’t be choosers in this here city.

In one of his pictures, he looked like he was posing for his MBA yearbook photo. In another, he was wearing pastels on the beach with friends also wearing pastels. While I don’t have a physical type per se, I usually avoid the salmon shorts-boat shoes-Vineyard Vines types. Call me judgmental, but something about them screams #AllLivesMatter. As the product of a North Jersey prep school and a less overtly preppy Ivy League university, my childhood and adolescence were filled with interactions with these types, hence my now informed adult avoidance.

His profile was pretty sparse, so I didn’t have much to go off of besides him being seemingly pretty nice and normal in the sea of “Heyyyyy sexy mami, I been waitin for you all my life” messages. Also, I noticed he checked off White AND Latino under race, so I figured he’s gotta be semi-down with the get down and is maybe like half Puerto Rican or something, right?

Anywho, I show up to Dinosaur BBQ ready to throw down on some brisket and he’s already seated at a table by the door. He stands up to hug me and that’s when I see the cargo shorts, New Balance sneakers, and tucked in Polo. Triple cringe. His alleged Puerto Rican-ness is nowhere in sight, but his Justin Bieber wispy hair was in full effect.

We actually had a decent amount in common. We both went to competitive universities, his dad’s also a doctor, his sister was also in medical school, and his roommate was also in grad school at Columbia. He asked me where I lived and I said just a few blocks east in central Harlem. He replied that he walked up the 10 blocks from his place in Morningside Heights, a neighborhood also known as Harlem but its white residents prefer to call it otherwise. Then came: “Yeah it’s a sketchy area around here. While I was walking, I felt like an open target!” Red Flag #1. He laughed and I snickered because that’s what you do on first dates – laugh at all their lame jokes. But as I bit into my cornbread, I wondered…an open target for what? For gangbangers to roll up on you and jack you for your Metrocard? “Why of course you feel uncomfortable walking in a neighborhood where no one looks like you! I feel the same way in the Upper East Side!” is what I should have said. But instead, I swallowed my bite of brisket and moved on.

Conversation flowed pretty easily and naturally it steered towards work. I learned the ins and outs of the startup where he served as the CFO and discovered just how uninteresting finance truly is. He asked me what I was doing before grad school and I explained to him the non-profit I worked for that champions educational access for students of color. He seemed pretty interested and picked my brain about the process of placing high-achieving students of color into prestigious private schools around the country. We even went over the mission of the organization, how we selected our students, how we worked with the partner schools, and the life-changing outcomes for many of the participants. He commended me for a job well done and I was feeling real good about my place in heaven at that moment.

But then came Red Flag #2 when he hit me with the “Well let me play devil’s advocate for a moment.” I nearly choked on my potato salad when I heard him say this because I knew what was sure to follow was some offensive ass shit that was going to expose how he really felt while hiding behind the cloak of the devil.

“So let’s take affirmative action at universities…wouldn’t you say unqualified students of color are essentially taking spots from students who have the grades to get into the school? Aren’t we then setting up those students for failure since they didn’t have the grades to get into the school in the first place? Wouldn’t they actually be better off at less challenging schools where they can succeed at their level?” His Fox News soundbites seemed to go on and on and on… And with each question he asked (on behalf of the devil remember), my anxiety rose high above the clouds.

They say to avoid religion and politics on the first date (which I now understand) because no one should have to Trevor Noah a bitch from the jump (which is exactly what I had to do). Fresh out of my first Teachers College summer class, Legal Perspectives: Affirmative Action in Admissions in Higher Education, I let Dan have it. I one-two punched him with some knowledge about how exactly affirmative action in admissions works since his “unqualified students taking qualified students” Rush Limbaugh-isms were incorrect. I then laid it on thick about how low expectations for students of color has been proven to weaken their academic achievement and the importance of placing students in challenging educational environments, not positions where they’ll “fail” as he calls it.

I was eventually able to steer the conversation away before he brought up police brutality and I was going to have to one-two punch him for real. But, one might say I was pretty shut down from then.

First dates are designed to scratch the surface of a person. We put on our best face, tell our best stories, and keep things light and airy. We avoid religion and politics for fear of shit getting just a little too real with a stranger whom you’re supposed to be impressing, not scaring off with your ideologies. However, while I sat across from Dan begrudgedly explaining black oppression and justifying the obligation for this country to address race-based obstacles that have obstructed the path to success for people of color, I was simultaneously thankful to him for cutting out the bullshit and bringing our conversation to this point. I could then dispel any notions he had of finding himself a pretty, “safe” black girl to date who wouldn’t bring up the racial elephant in the room and instead let him know that beneath my upper-middle class prep school upbringing and long straight weave was a Malcolm X sympathizer not afraid to call you out on your white privilege by any means necessary.

I’ve come to realize in dating, there are some basic non-negotiable values you have to have. Twenty-year-old Natasha would draw a hard line at 6’2’’ and a swimmer’s body. Today, I need you to know your place in gentrification and not argue with me about social stratification. Generally in life, I elect to not surround myself with people with conservative political beliefs, which is pretty easy in the blue states of New Jersey and New York AND thanks to the “unfriend” button on Facebook. While dialogue with people of varying backgrounds and opinions is necessary, when it comes to dating, it’s exhausting. There’s a minimum level of wokeness I require, and I’m pretty sure Dan didn’t take that Race Relations in America elective in college hence his inability to recognize that his comment about getting jumped on his way to the restaurant was just a little bit microaggressive.

In the online dating world, however, with profiles filled with Snapchat filtered selfies and talk of “loving to travel and hunting for NYC’s best tacos,” it’s a little bit harder sifting through people’s Stepford facades to discover what their stance on abortion is. On my OkCupid profile, my summary isn’t leading with the fact that I’m a pro-choice, #BlackLivesMatter, anti-gun socialist, but maybe it should? And on the flipside, I just need to know the answer to one question: who’d you vote for on November 8, 2016?

To be fair to Dan, I don’t even know if he really was a Republican. I could actually see him being a Bernie Bro turned non-voter, which ain’t really much better. Nevertheless, my summer boredom and Dan’s cute face blinded me enough to keep us messaging each other for just a few more days.

That following weekend, he was going out of town for July 4th with some friends and I asked him where they were headed. “Nantucket!” he replied. “Have you been?” Red Flag #3. At this moment, my eyes rolled so far back in my head, my eyesight hasn’t been the same since. I told him I hadn’t, but it was a place girls from my high school vacationed frequently so I was pretty familiar with this summer playground for old money white privilege (No, I didn’t actually say that). He replied, “You should go sometime. I think you’d really like it!”

Andddddd scene. It became ever so clear that Dan and I live on different planets, perhaps in different galaxies. I would probably enjoy Nantucket. After living a life of being the only black girl, sometimes person, in the room, I can certainly move it and shake it with a group of rich white people with so much ease that they’d probably forget there was something different about me. Meanwhile, homeboy felt uncomfortable in his 10 block walk to Dinosaur BBQ… *sideye*

About three weeks later, I was at my friend’s apartment watching How to Get Away With Murder when a Snapchat notification popped up on my phone. Dan had added me as a friend. I rolled my eyes and laughed while consciously not adding him back. Ten minutes later, another Snapchat notification. I open up the app to see Dan had sent me a video. I click open and staring into the camera is Dan to my horror. He blows a kiss and then “I Love You” appears in a heart on the screen in the early days of Snapchat filters. And here we have it: Red Flag #4, which was irrelevant because I was long over Dan and testing out a new dating app called Soul Swipe by then.

*I didn’t bother to change the name because…fuck Dan.


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