Dating Outside My Comfort Zone: A Night Out with Dill Pickle

A blonde night of steak with a side of idks.

I went on a date with a white man for the first time. If I could put it into one word, it would be interesting. This is not on brand for me, so throughout the process, I try to be very careful with my words.

The Initial Meet:

It’s 8:40 at a bar, Thirsty Lion Gastropub & Grill, which I’ve never been to, but I let my homegirl pick the spot. I was meeting my social media bestie for dinner because she was in town for a job interview. Now, homegirl is a restaurant industry vet, and she’s scoping the scenery out. At the bar, the seating is homegirl, me, and Dill Pickle (his nickname). I am sitting down, waiting for the bartender to bring over the Tito’s Winter White Cosmopolitans we ordered. In no shape or form am I looking toward Dill Pickle, but homegirl strikes up a conversation.

My brand is very: black queens forever, snow bunnies never. Shoutout to Dr. Umar. Anything going on here is casual, but before the night ended, we exchanged numbers and went our separate ways.

Date 1:

It’s 4:30 p.m., my hair is done from going to get silk pressed out for Kamala Harris, and I’m in the bathroom putting on my shapewear to put on what I like to call my “Porsha Williams dress.” To me, it resembles a confessional look, very cutesy, very demure. Brent Faiyaz is playing in the background, and my sister is talking over my music on FaceTime. This is a normal routine for my Friday night. I’m headed to support my cousin at a happy hour event she planned, and I’m excited to mix and mingle when I get a text from Dill Pickle. Instantly, I’m nervous because I am like, what does he want, and what do I say? He asked if my homegirl and I could meet up and have “some fun.”

My first thought is, what is his idea of “fun?” I grew up in the suburbs, so I understand that “fun” for the less melanated can mean a wide range of things. At first, I chose not to text back and sent my homegirl a voice note saying, “Girl, you got this white man on my phone.” But then he double-texted. He said, “Or me, and you can just go to dinner.”

I was shocked and appalled. Did I get chosen by a white man? This isn’t to be confused with it being rhetorical or excitement…it was pure confusion. I felt like I didn’t know how to be. Like, will he get me? When I’m outside, I am rarely approached. I’m a dark-skinned black woman in a city and time where interracial dating is heavy and praised. So it’s never me doubting myself; it’s me doubting others’ intentions with me.

One thing about me, though, is that I will do stuff for the plot. So I accepted the offer, especially after he agreed to take me to a steakhouse I had never been to. After I went to happy hour with my cousin, I met my white king at a four-dollar sign on Google restaurant.

this is when I realized...i'm too fine for a white man

When the waitress came, she asked what we were celebrating, and he quickly responded that it was our first date. His energy honestly took me aback. It was refreshing, yet scary. We split a bottle of wine to share, and he said his budget was $120-$150, which was way more than the budget of the Starbucks date I was offered last month. We chatted over “whatever I wanted,” which was steak, potatoes, and a cheesecake to end the night. While I was impressed with the ambiance, the service, and the food, I felt our conversation was lackluster. Was it that we had nothing to relate to, or was this a typical first date? Many thoughts were running through my mind, but I decided I would accept this experience as is.

Before dinner even ended, he expressed how he didn’t want the night to end and asked if I would join him for drinks. Of course, I said yes, and we headed to a familiar wine bar. Now…this is where I learned it would never work…even though this reasoning may be petty. The wine bar was bumping some good music, I’m talking 90s-2000s R&B, and this man didn’t bulge once. He also asked me what the last place I traveled was, and when I told him to see Usher in Philly, he told me he hadn’t heard about Usher in years. That’s when I was convinced he lived under a rock.

cheesecake from dinner

When one of my favorite Chris Brown songs, "Forever," came on, I couldn’t even engage in conversation because I was jamming, and he didn’t say anything. It seemed petty, but I knew that this could never work.

Again, eager to see me again, he set the next date before we left. He asked me what was on my list of things I wanted to do in the city, and we decided to go to the Perot Museum. I was moved by his assertiveness of wanting to see me again. But in the back of my mind, I was truly questioning his intentions. Our conversations flowed, but there were no sparks, commonalities, or anything. We talked about work and everything straightforwardly but with no fluff.

The After Thoughts:

Why couldn’t I have this same experience in black? Does it exist in 2024? Can it exist? On social media, there’s so much propaganda on what to do and not to do on a first date and what to spend, especially from black men. So, to experience the opposite, I needed to know that it existed. It was refreshing not to think about the politics of dating and enjoy being spoiled without thinking about the optics. He picked the place and time. He paid, and there was no fuss about it. I enjoyed the ambiance of the date and was willing to see him again.

As a girl who likes to laugh, I like to kiki, I like a jokey joke, and there was none of that. No banter or anything. That’s what I didn't like. The conversation was pretty baseline, and I understand it was the first date, but I don’t know. I am a person who craves deep connections, so regardless of race, I knew this wasn’t it.

Nothing connected us, and I also noticed some major red flags. Nonetheless, I agreed to the second date because I needed this data. I mean, that’s what dating is. My lingering question was, what’s more important…love or legacy?

Dill Pickle told me that he worked under the CFO of a construction company. He persisted in telling me about wanting the money, the status, and the fortune. As far as attraction, there was zero. He’s small. He was shorter and smaller than me. I’m about 5’4, he was easily 5’2. He has no facial hair or swag but a cute baby face. He reminds me of someone who’ll be your favorite friend from 3rd period Geography class and the one you would pick to work on a group project with. Mind you, this falls in line with nothing like the other white men I like: Justin Timberlake, Robin Thicke, Channing Tatum, or Paul Walker; you know, the typical. He was not a blue-eyed soul in the slightest. For me…personally, it gave nothing.

So I’m battling, is it the cultural differences, is it his looks, or just that he’s white? I kept thinking if he was taller, had more muscle, had some facial, and was a little rougher around the edges but still white, would I feel a tingle? I knew how much culture and family dynamics meant to me already, but when presented with this opportunity in my face…literally in black and white, it hit me more like a ton of bricks.

I was excited because it was a new, fresh storyline, but I felt so empty—very unfulfilled. One of my homeboys said you honestly said yes to the steakhouse and not yes to the man, which was accurate when I looked back on it. I said, “You got me there,” and laughed out loud. I still *halfway* believe in my fairytale ending, which includes somebody’s son who has lips.

But I’m unsure if date two made me feel better or worse…