DOOM20: The ★☆☆☆☆ Date of 2018

From the NYPL Digital Collections

This is the first entry in a series commemorating my upcoming 30th birthday. 30 is a large milestone, one that invites reflection on the last decade lived and the notable events that occurred. I’ve cherry-picked a few moments that live rent-free in my head to feature in what will be known as the Distinctive Occasions Of My 20s, or DOOM20 (can you tell I work in pharma?). Some stories will appear more grandiose than others to the naked eye, but I assure you they’ve all played important roles in shaping who I am today. As I don’t have the greatest memory for conversations, in lieu of quotes I’ve provided extremely close approximations of dialogue to avoid misquoting someone entirely.

Dating in New York City is not for the faint of heart. The modern dating scene is already perilous when taking into account the prevalence of The Apps, whether it’s Tinder, Hinge, or any of the dozens of other companies that have spawned in the last decade. When thousands of eligible singles are just a swipe away, many swipe without abandon (men in particular). A match is something to celebrate, though conversations within the app can peter out at a moment’s notice. A conversation may go well, but not always lead to a date. A date may be agreed upon, but then canceled last minute. A first date may actually happen, but a second is never guaranteed. The sheer size of the NYC dating pool amplifies the faults of The Apps, as there’s always an endless stream of potential suitors to replace one’s current infatuation.

My experience with dating in the city has been checkered at best. I’ve had my fair share of ghosts, catfish, and other creatures associated with dating. I could have written the entire DOOM20 series as a chronicle of my dating life, highlighting the quirky women I’ve encountered and the shenanigans that ensued. The first date I ever went on in the city was with a polyamorous woman in her apartment with her gay friend where we watched How I Met Your Mother while eating Thai takeout. I spent the first few hours of January 1st, 2020 wandering the streets of Brooklyn, waiting for a follow-up to an invitation text that would never come (the first indication of how amazing that year would be). Friends who I regaled stories of my dating life to have told me that they’d make for a great collection of essays. Today, however, I will explore one date in particular that, to this day, stands out as one of the weirdest.

One of the first elements of this date that made it so fascinating was that I matched with Brenda (not her real name) on two different apps. Singles often mingle on a rotation of apps, so it’s not uncommon to see the same people with profiles on multiple platforms. The first app I matched with her on was JSwipe some time in 2017. Conversations within JSwipe disappear after 18 days of inactivity so I can’t confirm any of the details, but the conversation was good enough to warrant exchanging phone numbers. She provided her number, I sent her a confirmation text with my name, but she never responded even after I wrote back to her in the app. That typically doesn’t happen once numbers are exchanged, but the quality of the conversation in the app probably made me decide not to pursue her further. When your soulmate is potentially just another swipe away, one can’t let themselves get hung up over people who don’t take communication seriously.

The second app we matched on was OkCupid in February of 2018. Once again I can’t confirm the details of the conversation since messages on the platform are removed after a certain period of time, but I can assure you we had another conversation worthy of exchanging phone numbers. It should be noted that I knew it was the same woman who’d ghosted me from the outset, while she didn’t remember who I was. I have a great memory for betrayal, but at the time didn’t hold it against her. As mentioned previously, dating in NYC in The Apps Era can be exhausting, so the fact that a conversation may have been lost in the shuffle isn’t farfetched. In fact, once she saw both my first and second confirmation texts she apologized for missing it the first time. With her full attention, we were guaranteed to meet IRL.

Having a “regular” date spot is generally frowned upon in dating culture, as it could be seen as “boring” by someone who discovers they’ve been taken to one, while also making it harder for the one who planned the date to have a unique and meaningful moment with a potential new partner. On the flip side, if an establishment provides consistent quality, it can be tempting to fall back on a familiar haunt to try to make a good impression. Ideally one wouldn’t have to have a first date spot, but as we can’t all be lucky enough to find our person on the first go around, some of us will eventually endure enough first dates to find a place that sticks. 

Image uploaded by Waldy himself to his restaurant's Yelp page Waldy, of Waldy’s Pizza, with a pizza.

As luck would have it, I found what I thought was a good first date spot at the now closed Waldy’s Pizza on 6th Avenue between 27th and 28th Streets in Manhattan. I initially discovered Waldy’s in 2014 while looking for a bite to eat with friends while hanging around Herald Square. The food was reasonably priced, the restaurant had a laid back, intimate atmosphere, and I genuinely enjoyed the pizza. Their pies were not a traditional circle, but instead more of an ovoid flatbread, which at the time I felt added to what made the spot special. I’m not someone who genuinely enjoys drinking, so if I had the power to shift a date away from a typical bar atmosphere I’d do whatever I could. Waldy’s was a little too far from my office in Herald Square to run to pick up lunch during the workday, but for meeting up with someone after 5:00 I couldn’t ask for a more convenient restaurant.


Before asking someone out to Waldy’s, I’d first ask them “do you like pizza?” This was meant to be a playful question, since who in their right mind doesn’t like pizza (it also doubled as an allergy assessment, for if someone was gluten free, lactose intolerant, or couldn’t be within 50 feet of a tomato I’d have to come up with a Plan B)? When I posed the question to Brenda, she wholeheartedly said yes. She had never been to Waldy’s, but she assured me she enjoyed trying new places. The pizzeria happened to be smack-dab between both of our offices, so neither of us had to go too far out of the way. On the day of I arrived 10 minutes early since I have a terrible habit of giving myself way too much time to get lost/go on adventures. Brenda arrived at just about the agreed upon time. After exchanging pleasantries we walked inside, and the date commenced.

One of our first topics of conversation after placing our order was how I came to pick Waldy’s in the first place. I explained that I had been there before and had good experiences with it. She went on to tell me that she was on a quest to join the Yelp Elite Squad, an exclusive tier of Yelpdom that rewards members with special events and other perks. She was writing Yelp reviews left and right in an attempt to catch the eye of those who recruit for the squad, and asked if it was okay with me if she wrote a review for Waldy’s. Thinking she’d perhaps take notes and compose her review after the fact, as well as eager to see her laud my restaurant selection, I told her it was no problem. While waiting for our food she pointed out different features of the interior, such as the selection of alcohol and the lack of a public restroom. I nodded along and tried to pepper in my thoughts, but she was intent on analyzing every little facet of the restaurant.

Another photo Waldy uploaded to his restaurant's Yelp page. An approximation of what the interior of Waldy’s looked like on that fateful night.

The arrival of our pizza halted her live review, save for saying how good the pizza was. We ordered a pie to share, and it was impossible to escape the good smells wafting from the board it was served on. I was initially nervous about how she felt about Waldy’s after listening to her critique it from top to bottom, but I had high hopes that the food would alleviate any of those concerns. 

After finishing her first slice, Brenda took her phone from her bag and started to write her Yelp review in real time. Taking one’s phone out on a date is a generally accepted faux pas, aside from emergencies or showing pet pics. Brenda showed no shame, tapping away as I worked on my second slice. She did her best to keep up with whatever conversation we were having at that point, but her attention was elsewhere.

After several minutes, Brenda emerged from the glare of her phone with a grin on her face, announcing that her review was complete. That news came as a relief to me, thinking that we’d finally be able to engage in a deep, meaningful conversation. To my dismay, Yelp would continue to be the topic of conversation. Knowing that I was a copy editor, Brenda asked if I would do her the honor of editing her review before posting it. Always the people pleaser, and genuinely curious about what she wrote, I agreed to the pro bono assignment. I accepted her phone from her outstretched hand and started to read as she resumed eating.

The star count was on the top of the page, so the two grayed-out stars of the five present was the first thing to catch my eye. I looked up at Brenda with a raised eyebrow, but didn’t protest verbally. I was disappointed that she didn’t feel Waldy’s deserved the five stars I’d give it, but I should have expected the mixed review given the points she’d raised throughout the date. As I continued reading the post, I occasionally pointed the phone back to her to suggest an edit to her grammar or word choice. Instead of being grateful for my professional editorial opinions, Brenda objected to almost everything, saying that it was actually she who was correct. Since I wasn’t getting paid to make sure her review was accurate and error free, it wasn’t worth fighting over.

Once we finished the pizza, it was time to depart. As we gathered our belongings to head out, Brenda noticed the selection of potted herbs near the shakers for garlic powder and red pepper flake that patrons could harvest to add to their pizza. She mentioned that she would have bumped her review up to four stars if she’d seen that. The chill of the February air was a shock after spending a good deal of time by the heat of the wood-fired oven. I offered to walk her to her subway stop, but she declined, thanking me for paying for the meal before quickly taking her leave.

At the time of this date, I was in a phase where, even if the date didn’t go exactly as I’d planned, I still wrote back to ask about a second date. I consider myself to be an acquired taste, so what better way to endear myself to someone than repeated exposure? As such, even despite the Waldy’s slander, I texted Brenda once I returned to my apartment that I’d had a good time, and that I was looking forward to seeing her again. She replied later that evening once I had gotten into bed, saying she had fun, but didn’t see a future for us. I considered texting her back, but since I pride myself in dealing with rejection gracefully I left it at that.

My opinion of Waldy’s never changed, though after Brenda’s poor review I did think twice about what a first date at a pizza place said about me and my intentions. I’m a diner who prefers a low-key meal to a white tablecloth experience, so there was a part of me that appreciated how Waldy’s could filter out pretentious eaters from those who could appreciate good food no matter the venue. I also understood that sometimes morals have to be sacrificed in the name of courtship. I still brought a few potential suitors through Waldy’s up until the onset of the COVID-19 pandemic, but I became more open to alternative locations.

2020 was a year full of reflection and reconnection. It should come as no surprise then that, in the midst of lockdowns and quarantines, I was inspired to find Brenda’s Yelp review to see if it was as bad as I remembered. I eventually found it after scrolling through hundreds of extremely positive reviews. Her lousy three-star review stuck out like a sore thumb. As I read it then, and even now as I have it open again to write this post, I was struck by how unfair she was. Was she mad enough that I didn’t take her to a place with a waitstaff that she made it a crucial part of her review? How did she know the pasta was “mediocre” if we didn’t order it? Did she really think her grammar was better than mine when she had the audacity to start a sentence with “And?”

One thing that did make me feel a little better about the whole thing was that, despite (or perhaps in light) of her very critical review, Brenda never did make it to Yelp Elite status. Restaurants like Waldy’s were spared from users treating her critiques with more weight than any other salty Yelp review.

Honorable mentions for other important moments of 2018: Hunting Mr. Mime in Spain; Winning The Great Editorial Bake-off

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