The Things I Thought We’d Do Together

This year has been, to date the most fun year I’ve ever had.

It feels like it’s the first time I’ve ever felt like I’m living the life I’ve been building towards. Until now, my life has mostly focused on accomplishing educational and career goals, leaving the thrilling, fun and adventurous side of my life missing in action. This year for the first time, I’ve been able to add some color to my book of life by doing things on a whim.

My military lifestyle as a child solidified my relationship with travel, which means I don’t generally crave it as much as I crave steady, stable environments. That said it has become common for me to leave the country every couple of years on my birthday to do solo adventure trips, not because I desire to travel but because I hate the pressure of having to plan for it. Privately, I’m also alaways terrified that if I were to plan something no one would show up (this is likely an irrational fear, but it exists).

This year however, instead of burying my head in the sand of a far away country, I randomly bought tickets two concerts: Maxwell and Jazmine Sullivan. Both events were phenomenal but it wouldn’t be until later in the year that my appetite for more experiences would begin go grow thanks, in part, to Vegas.

The Catalyst

Last year, rumblings of an epic concert were being made. The Lovers & Friends Music Festival, an experience that centered on the smooth R&B music of my teen years. I decided quickly that this was something I absolutely needed to be apart of. This event would not only mark my first time visiting Vegas, but it would also be one of the few times in my life that I’d invite someone to go along with me.

It was over 100 degrees in Vegas. The concert was on asphalt and lasted from noon to midnight. It was hot, crowded and time consuming- and I enjoyed every minute of it. I wore clothes I normally would never wear, I danced and sang, flirted with strangers, exchanged numbers, contemplated making out with someone I’d just met and allowed a man to shower me with attention for the night. It was more fun than I had ever expected.

When I got home, I was in a tizzy. I had been working so hard all year that the taste of fun lit a fire under me. It was clear I had only gotten a sample of what a more adventurous life could feel like, and soon enough I wanted a full meal. This pushed me to ask an even deeper question. Why had I not been having full meals of fun in the first place?

After some serious head scratching I realized there were some things I needed to admit to myself- out loud. This was when it donned on me that I had been holding myself back from experiencing new things because of my reliance on my friends (enter the previous post). But I knew it was something deeper than this. Somewhere in Whitney’s world of fantasy, I had subconsciously assumed that the most exciting parts of my life would begin when I met my life partner- someone who would ultimately like the things I’d like, or who would learn to grin and bear it- like me. Essentially, for God knows how long, I had been waiting for the friend I never had to show up and do life with me, willingly and enthusiastically, while also exposing me to new adventures.

This threw me.

How long had this been in the back of my mind? How long had I been waiting for this person to rescue me from my ordinary life? Was it even fair to have this kind of expectation for someone? And what if I did find him? There could be no way to know that the behavior I took on with my friends wouldn’t transfer to the relationship I’d have with my partner. If I routinely prioritized their wants, needs and sense of adventure over mine in the past, who is to say I wouldn’t prioritize his in the same way? How could it not inevitably lead to a consistent cycle of being unfulfilled?

It was time for me to stop waiting and to do the things I thought I’d do with my person- on my own.

I immediately got to work booking more trips, concerts and events.

This year, I went to a boxing match for the first time. Unaware that the start time on the ticket is not in fact the start time of the main event, I sat through it all, by myself and enjoyed the shit out of it. Shortly afterwards, I went to the US Open, and missed Serena’s last game by one day. This was not my first US open, I had gone to one many years prior, and sat high in the stands with my colleagues for an office outing. But this time it was different. I sat with strangers and was in awe at how noisy and communal the game could be.

I also went back to Vegas.

The Lovers and Friends Festival in May gave me a taste of Usher, but I wanted to experience more of him at his residency and this time on my own. I also did not realize until I went there the first time how many amazing chefs and restaurants had been pushed into one region of the country. Because of this, I had a new goal: eating my way through Vegas. I took it upon myself to document my trip on my Instagram, which is something I normally would not do. Not only did I document my strip via IG but I also did three different self-administered photoshoots each night I went out.

My Usher experience happened on the first night of my arrival and it was everything I needed it to be. I found myself sitting next to Simu Lui and a host of other interesting people. The next day, on the way to the pool, I ran into Nathan from Insecure (Kendrick Sampson) and embarrassingly blurted out “HEY!” as if he and I were long lost friends (I then hid at the pool the rest of the day).

My other experiences were just as amazing. I ate at a restaurant with a waterfall in the the building. I connected with random strangers at a bar during brunch. I turned down way too many free drinks from random people. I gambled with another man’s money who gave me $200 for my time. I took a risk and ventured off the strip to eat an unforgettable tasting menu at E.D.O (literally danced in my seat at every plate they brought out to me). The trip ended with me reuniting with friends from Chicago I hadn’t seen in a while who were also in town to see Usher. It was hands down, 10 times more fun than the first time I had gone.

But I still had one more adventure up my sleeve: Art Basel

Like Vegas, Miami is not a place I find the need to visit often (or at all), but this year, I was determined to go to the event that I had only ever watched through my phone.

I picked a hotel that I wasn’t even aware was in a great location. I stood in a long line at midnight at Choyo Taco and quickly realized it was worth the wait. The next day I stared into the abyss a Sarah Meyohas painting and wondered if I were standing, floating or sinking. I found and fell in love with Derrick Ofosu Boateng’s work and bought an art book by Maudy Alferink. I spoke with art collectors and gallery representatives and became jealous of the people who have had the privilege of living in that world longer than me. I met some of the most interesting people, partied and ate at Soho Beach house, danced next to my crush, Anthony Ramos, and ran into old Chicago friends (again!). Most surprisingly, I went on three pseudo spontaneous dates with three very different, chivalrous and amazing men who made sure to take care of me. The trip ended with a delicious meal at Sunnyside café before getting a free ride to the airport.

I came from that trip thrilled with the a new sense of existence. What had I been doing all this time that this had not been my life? I will say that as I’m planning my 2023, I am also realizing that I am, apparently, very expensive- and that’s okay.

I’m looking forward to seeing what the next, more intentionally “me'“ focused year is going to look like. Stay tuned.