I'll start here: My hometown in Florida. A heavily Hispanic and white populated area and one of the hardest places to grow up Black. 
With so few people looking like me, there were only three categories I could fall in to, the Black people, the West Indian Black people and people like me (who never owned or even qualified for a legit "Black card").
My Black underachievement started at home. My mother was born in Trinidad. Sounds like I belong in the West Indian Black people category, right? Nah. My mom had me at 38 years old and her days of whinin’ and parangin’ were far gone by the time I was old enough to really embrace my Calypso-Caribbean culture. She had also grown stronger in her Christian faith, became an ordained minister and was going to make sure that the fear of God kept me so petrified I physically couldn’t stray from the straight and narrow. And she didn’t know much about Black American culture even if she wanted to teach me. If it wasn’t gospel music, I wasn’t listening to it. If it wasn’t on the Christian network, I wasn’t watching it. And on family movie night, while other people gathered to watch Sister Act (1 and 2) or The Preacher’s Wife, I was watching The Passion of Christ or Veggie Tales. My free time was spent in church at least twice a week, and even now at 22 years young, I can recite lesser-known bible passages before quoting Love & Basketball.
Besides, back then, I didn’t feel like I was missing out on anything, and I never thought I was different. Until I met my first Black friend, Jen.

I didn’t have many friends other than the Sunday school kids that grew up on the west side of Orlando. While we connected over church, I really didn’t fit in because when I could understand them beyond their thick southern accents, they’d rather talk about music I had never heard of, dances I couldn’t do or a number of things I had no interest in because I had never been exposed to them. 
Jen wasn't much different, but I needed a friend like her because she looked like me.
Jen had two older brothers, Jeff and Jason. Jeff and Jason were, to put this nicely… a**holes. But Jen adored them, as a sister should, so she followed whatever they did no matter how cruel. And eventually Jen turned from my childhood best friend into my childhood bully. When her brothers weren’t around, her and I would play with our Bratz dolls and she’d refer to me by my proper name, and as soon as they rolled up on their big-kids-on-the-block bikes, she’d join with them and do things like convince me to eat sand or call me by my unwanted name: Burnt Pretzel. They said one day they went to a shop and saw a pretzel that was so burnt, it reminded them of me. 
Fast forward a few years and Jen moved out of the state. Crazy enough, I was really sad. She was horrible to me, but it was the closest I had come to friendship. That was elementary school. Friendships came and went and none of them particularly long lasting.

By the time I got to middle school, it was a fresh start. I was determined to be cool, make friends and be popular. Except, none of that happened.
My school had a huge Puerto Rican population. Everyone treated them like the pinnacles of beauty and popularity: two things I lacked. I had to be like them and dress like them and play the part. That worked for a bit (as far as over-the-top "chongalicious" phases go). I mean, they didn’t hate me and they at least acknowledged my presence, but it was short lived.
But finally, one semester, a new Black girl transferred to my school. She was from the Democratic Republic of the Congo. She was Black and dark, like me, but something was different. She was pretty and people liked her.
We soon became friends. She didn’t dress or act the way I tried to act with the Hispanic kids, and yet she still had friends, so I got rid of my faux Latina ways and followed her. I did whatever she did in order to be accepted, too. Her name is Cora and Cora was my inspiration. 
I tried my best to look like her and act like her and she taught me how to love myself. If it wasn’t for her, I’d probably still have to take off my glasses to look at myself in the mirror or splash water on the reflecting surface to distort my image.
And then came high school, and due to zoning, we separated. I was alone again.
At my high school, the cool kids were the Black kids from the West side (the same crew I couldn’t connect with at Sunday school). They always sat in the front of the bus and had so much fun (mostly being cruel and making fun of the bus driver), so I slowly made my way closer to the front until they noticed me.
When they finally spoke to me, the first words I could think of came out of my mouth in the most overdone and horrific Black southern accent I could think of. I don’t remember what I said, and I probably threw in a “riigh chea” for good measure. I shocked myself, I don’t even know where I’d heard that from, but it got me in. I finally did it. I even joined the Black club called Umoja and I was part of the Black float at a homecoming parade. They even nicknamed me “Lil Oprah” for my passion for journalism. 
Eventually, I think my "smarts" got in the way and the same Black people I thought accepted me one day told me I sounded like a country white girl and they reminded me that I was "lame" every chance they got. But, been there, heard that. I stuck around because I had no one else.
Then came school rezoning; my saving grace. I was transferred to a new school and thankfully, the name-calling stayed behind.
By the time I got to this new school I had no desire to hang out with most of the Black people because they reminded me of those that had hurt me in the past (a prejudice that unfortunately followed me into my adulthood). The white people were the same rednecks I didn’t really mesh with before and I had well gotten over my Hispanic-phase.
I found my place within the theater and journalism departments where I met people that didn’t fit a particular category and didn’t make me feel like I had to act a certain way for them to like me. They were of all races and they couldn’t be defined. They simply were who they were, and I was simply who I've become: me.
I felt a shift that I can’t even explain how it happened. Maybe enough time passed. Maybe maturity came right on time. Maybe I'd had it up to here. Whatever the reason, all of a sudden, I couldn’t care less about trying to fit in. I got tougher and learned to hold on less to people and focus on my future.
Today, that prejudice I developed earlier on lingered in the back of my mind. It became more of an apprehension, a guarding of my emotions so that I wouldn’t let anyone else treat me the way I had been treated. And when time to apply for colleges came, I avoided HBCUs at all costs. Black people were the ones that didn’t accept me, so why would I want to put myself through four years of torture and constantly explaining why I thought Billie Holiday was a man for most of my life.
Goodbye, Florida, hello college in New York. 
Things changed. People in New York are different. There are Black people of all types. Hipster, bourgie, goth, rocker, alternative. I fit in. I didn’t make many friends, but it was by choice. Years of experience has taught me that I only need two or three really good friends at all times, and I have that, and yes, they're Black just like me. 

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(Photo: Ian McGregor Moran)