—Friday, June 22, 2012—
Holy shit — this was my 99th date. Only one more and I would be done. As such, this date excited me more than most others. Don’t get me wrong, the project had been fun, but I was looking forward its completion.
The other surefire reason to be excited about the evening was that my date, Ella, had come to me from one of my best friends in the world, a man whose opinion I trusted on most matters in life, save perhaps milkshake flavors (He preferred strawberry).
As the work day died down, I kept my fingers crossed that the chance of thunderstorms would stay at bay so that our kayaking excursion on the Hudson River wouldn’t be cancelled. If that had happened, I would have been far less excited about the night.
The mutual friend responsible for this date, Kevin, had told me some weeks earlier that Ella had heard about the project and was interested in going on a date. I was really glad that it had worked out, especially since there was such little time remaining and the only date left on the list was kayaking, which luckily, Ella was totally cool with. In fact, Ella knew Mutual Friend Kevin because they’d both worked at a summer camp where she had taught kayaking. So, that had lined up rather well.
Ella and I made plans to meet up at Chelsea Market, which I had never been to, but it was relatively close to her office and not far from the kayaking place. After playing phone tag with a potential Mom Date, I texted Ella to see where exactly she was and fortunately, I was only one block away. She said she was by the Market’s eastern entrance on 9th Avenue and wearing a red dress with “small dogs” on it.
I greeted Ella a minute or two later and she shook my hand, which seemed a bit formal, but not crazy. We’d actually met once before, but it was a couple years earlier and I hadn’t really remembered it. (In fact, Kevin had had to remind me of it.) Ella looked more or less like her pictures on Facebook, which I had liberally browsed through, except better. She was cute, tall, well dressed and altogether smart looking.
We stepped inside Chelsea Market and she began telling me about the different food options and how she worked around there. By the time we had taken a full run of the place, we were still undecided. As we turned around, she asked which date she was. As in, which number out of the hundred, sequentially.
“99,” I told her.
“That’s awesome!,” she said and high-fived me, which I loved.
“Yeah, it really is! I just have to date a mom now,” I replied
It was an odd thing to say. I never thought I’d would say those words until they had flown out of my mouth.
Ella asked me if I had taken Kelsey on a date yet and I was very confused. Who is Kelsey? Should I know who Kelsey is? Have I taken Kelsey out?
I asked Ella to clarify and sure enough, she was friends with the only Kelsey I knew — a fellow improviser in the city. “I’d go out with her,” I said, but I wasn’t even aware it had been an option. Kelsey and I had only met for the first time about three weeks earlier.
Ella said that they had been talking recently and that she had asked Kelsey if she knew me, since I was also an improviser. She then explained the project to her and Kelsey said that it was something she would do. Just think, when I had met Kelsey a few weeks earlier, I’d actually considered asking her out, but balked, and now I was out on a date with a friend of hers. I think the experts would call this an “insignificant coincidence.”
It was generally unsurprising that I might know another improviser in the city, but as far as I knew, Ella wasn’t involved in the improv community, so I was curious as to how she knew Kelsey. As it turned out, the two of them had formerly worked together. Knowing that Kelsey worked in fashion, I asked Ella if — and indeed, she was — a fashion designer. I found this really cool. I’d had no idea.
With plenty of time to kill before our kayak tour (Nearly two hours), we picked a sit-down eatery within the market — Friedman’s Lunch. We both ordered a beer and Ella went for a veggie sandwich while I got a salad. Very health conscious. Very thin of us.
With our previous conversation lingering, I sheepishly told Ella that fashion was something that I was actually becoming more and more interested in. Saying that I was becoming “interested in fashion” made me feel uneasy, but it was true. I had been taking more note of clothing and been caring more about how I presented myself. She laughed and said that Mutual Friend Kevin might have been trying harder too because he’d been asking her about suits the last time they’d hung out.
She also mentioned that she could hook me up with a discount if I wanted it, which was one of those nice tidbits of charity that people offered up on first dates, never truly expecting it to be redeemed. However, it could say a few different things:
1. “I have an in on something cool.” A bit of a boast, but everyone found ways to boast on a first date.
2. “You get to be a part of the club too.” Everyone appreciated inclusion.
3. “I want you to like me.” This was what it all boiled down to.
We’d throw these out at random times in our life when we were looking to make a good impression. I seem to remember telling my West Coast Date that I’d travel to far off lands with her, which was true, but unlikely. As such, I didn’t take Ella’s offer too seriously — she could have been nervously word vomiting, albeit quite politely.
Light dawned on Marblehead as I finally realized that Ella must have meant to write “small dots”* in her text message earlier, not “small dogs,” because her dress had hundreds of small white dots on it. I told her this and she laughed at me. We talked about how funny autocomplete and autocorrect mishaps could be. (Someone should make a website!!!)
We talked about North Carolina, where Ella was from, and Massachusetts, where I was from, comparing people’s perceptions of them both. Both of us had grown up feeling ever so slightly separated from our hometowns because our parents weren’t really the standard demographic for our respective areas. Neither of her parents were from NC and neither of mine were from MA.
Humorously, she told me that she’d come up with some fun ideas for this date, all in the vein of making light of OHD, which I greatly appreciated. Specifically, she said she had wanted to get all my other dates organized to run into us at various points during the night. I couldn’t even imagine — that would have been so funny. It was odd, but I didn’t think I had ever run into another woman I’d dated while on a date, at least not without expecting it (I ran into Hiking Date while on Breakfast Date, but it was somewhat anticipated). After 98 dates, many in the middle or lower parts of Manhattan, you’d think it would have happened at least once.
The food was pretty good but simply getting to hang out with Ella was far more enjoyable. I mean, she had already casually mentioned “Jurassic Park.” The thing that helped the most though was that she was comfortable and confident, which took a great deal of pressure off of me.
Ella asked questions about the project but without exactly challenging it — her questions are all thoughtful and she seemed genuinely interested. Regarding dating, Mutual Friend Kevin had suggested to her that she take some Level 1 improv classes to meet desperate men and I agreed that it was a good recommendation if that was who you wanted to meet. We talked about the different places to meet potential mates and how the comedy world was filled with potentially desperate, often misguided men. She said that Kelsey had run into those types in the improv scene time and time again. I believed it.
I got to learn a bit about Ella’s work in the fashion world and we also talked about our siblings, which I appreciated. Overall, the meal passed by the way a good comedy show did, which is to say that at no point did I want it to end and I laughed a lot.
We got going eventually but there was no real rush. We still had plenty of time to get to the boathouse. She suggested walking the High Line, which was an absolutely excellent idea given the warm weather, so we found the nearest staircase.
Ella asked how many of my dates had come from the internet and she sprinkled in some other project questions here and there. We wondered about people who lived on the High Line — how they could maybe play pranks on people or, if perhaps they felt that their privacy was interfered with. (But maybe they were all about exhibitionism and got off on the voyeurs.) I explained how I had been really uncomfortable with exposing my body when I was younger and I was immediately reminded of having a nearly identical conversation with Madelyn that previous August on the High Line during our Stargazing Date.
It seemed crazy. Almost a year later and I was doing the same old shit. I guess I shouldn’t have been surprised.
Ella had previously felt similar about her body. Maybe we just matured into it? She said that she was the dorky girl for a long time but then she grew up and gained confidence and all that. It made sense, but there was something uncomfortable about leaving a former version of yourself behind.
That was one way in which this project had challenged me the whole way through. As much as I wanted to be the endearing, sensitive boyfriend of yesteryear, I was more and more aware that I now appeared to others as a typical single male. It was an image problem that I’d created for myself and yet it made me uncomfortable. Like all growth spurts, there were pain points, and I was just hoping to come out the other side stronger than before. It was puberty for my emotional and behavioral development. Those who knew me before may not have recognized me after the fact, but that didn’t mean I should be ashamed of the person I’d become.
We got off of the High Line however many minutes later and walked by a ballet studio where Ella had experienced her first celebrity sighting in New York. A man had come out of the studio doors with his arms spread wide and she thought someone was going to hug her. Turns out, it was just Antonio Banderas. Hah! That’s awesome. She was a good storyteller. I couldn’t do it justice now, but even the smallest things were fun to hear about when Ella described them.
In turn, I told her about my separate, but equally enjoyable, experiences meeting Michael Showalter and Michael Ian Black. It was cool that she knew their work so well. Once again, it was not that these were obscure people for comedy folks to know about, but I had no idea that Ella was secretly comedy folk. We also passed by her office, which was right across the West Side Highway from where we were going. As we crossed the highway, I lost my voice for a moment — a good sign that I was talking too much. I gained it back and finished my MIB story, but I needed to watch myself if I wanted to be able to speak for the rest of the night, and also so that I didn’t annoy the shit out of Ella.
Checking in at Manhattan Kayak Company, we were still a bit early, so we took our time changing into suitable kayaking clothes. With our similarly thin builds and similarly squarish glasses we must have looked like a we were on a totally adorkable** date.
While the other kayakers trickled in, Ella and I killed time out on the pier, talking with our New Zealand instructor Toby and our Argentinian instructor Mano. This was one of those situations were I started comparing myself to the good looking outdoorsmen with accents and experienced a twinge of jealousy over the fact that I would never know what it was like to open my mouth and have a woman turn into a puddle of human. I knew that looks, accents and charm weren’t everything but they were at least 75% of all things.
The rest of our time on the pier was spent making fun of standup paddle boarders. [Have you seen these idiots? It’s like, shut up, we get it. You look like a tool.] We also discussed how it was easy to forget that Manhattan was an island, but Ella apparently took the B to work and went over a bridge each day, so that helped.
Damn. Ella was super witty and very funny and we were both laughing a lot. Hers may have been sympathy laughs, but she was genuinely cracking me up.
Finally, it was time for kayaking. The sun had just about set by the time we received our brief lesson on how to kayak, and as the sun lowered itself into the bathtub of the west, casting beautiful purple hues over the fair state of New Jersey, we were out on the water.
As we ‘yaked down the river, Ella and I stayed close enough to talk occasionally and for me to accidentally bump her every once in a while. The largest group on the tour was a bachelor party, who were talking plenty, all trying their best to give their buddy the lamest send off in the history of weddings.
I called out a few uninteresting things about Hoboken and Jersey City, as they came into view. We paddled pretty much the length of Hoboken. You could see the border between the two Hudson County cities where the height of the buildings took a dip. Not to let me look too smart, Toby spouted off some fact about the Lackawanna train station tower at Hoboken Terminal.
We passed a large party boat blasting music and Ella asked me what I thought it was like to be on the other side. I think she simply meant to point out that this boat was the total opposite of what we were doing. We talked enough to stay entertained and to be somewhat endearing, all while a light rain began to fall on us. She said she was glad that I also had glasses on so that she wasn’t the only one with water droplets obscuring her vision.
Across from the southern tip of Hoboken, we turned around and retraced our paddle strokes. For the entertainment of all, Ella dared the future groom to paddle backwards for a while, which he did, until he lost his breath. It was a faster trip back uptown and we went far enough for me to point out the building where I worked in Midtown. It was really fun.
By the time we were back on shore, we were both wet and probably a little tired but there was a good sense of accomplishment. We got changed and I rinsed off my legs, using a spare t-shirt as a towel, as I was incapable of dealing with any amount of griminess or dirt in my shoes or undergarments. Basically, I was a major wuss.
We thanked our kayak guides, verbally and monetarily, and left the boathouse. Ella thanked me for financing the experience, but really, I should have been thanking her for doing it with me. Not only had she made my 99th date possible, but she had done it with enthusiasm.
As we crossed back over the West Side Highway, she asked if I wanted to go to the train or if I’d be up for getting a drink or whatever. I definitely wanted to get a drink or whatever. We walked down to the Meatpacking District with the intention of hitting up that one dive bar that was there, Hogs & Heifers Saloon, since neither of us had ever been.
Returning to the topic of fashion on the way down to the bar, and as we passed by a plethora of boutique shops, I told Ella about a recent date of mine who was a beauty and vlogger and also, about a male fashion blogger that I had recently started following. I lamented about the sizing of most mens clothing and she told me a few things about how sizing differed depending on the target audience and quality of manufacturing. Cheaper things, for instance, typically had more variation in size than more expensive brands.
It was unrealistic that she would know the answer, but I asked Ella why all of my Original Penguin shirts were always long in the sleeves. They seemed crazy long compared to everything else I owned. She didn’t know the answer for certain, but suggested that it must be something to do with their fit models (Which were like live mannequins for designers). I had never heard of such a thing and I wanted to ask more questions about clothing design, but I refrained for the time being.
Also, I made note that floral print pants were EVERYWHERE.
Unfortunately, Hogs & Heifers had a $5 cover, which we did not want to pay, so we walked further down and over to the West Village. Sorry, Meatpacking, we tried.
A good friend of Ella’s worked at the restaurant Fish, so she thought we might be able to steal a seat at the bar. We talked more about clothes and fashion as we walked. I was loving it.
Fish was more packed than a can of sardines***, but her friend, whom she had gone to both high school and college with, suggested Oliver’s close by. We got to Oliver’s and saw that there were plenty of seats to choose from which proved her friend’s suggestion to be a great one.
We grabbed two spots at the rear bar and ordered a round of drinks. A gin and tonic for me; a whiskey something for Ella.
There were a number of things discussed over the next couple hours, and as we ran through the topics, I noticed us positioning ourselves a little closer to each other with each chance we got. Or at least, I was doing that. (What a creep.)
We discussed our families and I told her about my dad being a little backwoods and my mom being pleasantly suburban. Her family featured the same dynamic: one side a bit simple, one side more educated.
The booze in our hands got us talking about drinking and both of our hesitations with it when we were a bit younger. When I told her that I hadn’t started drinking until I was out of school, she asked why I ever began, but it seemed easier to tell her why I hadn’t done it in the first place. It turned out that she had the same reason for not drinking until she was 21. A good swath of alcoholism in the family could scare even the most impressionable teen straight. We both commented on how remarkable it was that Mutual Friend Kevin had never caved in and had remained a non-drinker to that day.
There were several of us in high school, maybe five total from our group of friends, who didn’t drink. The group dynamic, with so many Sober Sallys — and the rest never putting any pressure on us — was such that it was easy to avoid booze in high school. The partiers in that group were more focused on music and weed anyway.
Ella then told me another of her funny date ideas, one that would have needed assistance from Mutual Friend Kevin: Alternate Universe Date. This was where she would fid a group of people to serve as doppelgängers for my friends back home, and we’d run into them at some point, just like the Bizarro episode of Seinfeld. Her other, and perhaps even more bizarre idea, was to simply dress up and act like Mutual Friend Kevin, as if that was how she always looked and behaved. God, that would have been hilarious. Either of those ideas would have been insanely funny.
It was possible that we were getting a taste of that bizarro world anyway that night, simply by being out together. While we were certainly different from one another, it wouldn’t have been wrong to say that on the surface, Ella and I were two sides of the same coin. We had similar career and creative frustrations. We had similar families. We had similar friends. And while our facial structures were pretty distinct, our body types and fashion sense would probably have found us lumped together in a “young hip professional” line up. So many people I’d dated served as a contrast to everything I was, albeit quite well, and rarely did I find someone so complementary. It was kind of great.
As I told her more about my family, I found myself talking about my aunt and uncle in Japan and describing my experience with the March 11th, 2011 earthquake to her. I could feel the tears well up in my eyes and as I noticed them there, I felt like a fool of a Took for getting so emotional. Fortunately, I pulled it together before the levees broke. Once again, I was reminded of my Stargazing Date the previous summer because the same thing had happened. It was odd that these dates were so patterned in that way, but I guess that when I was near the High Line, I was compelled to talk about body issues and Japanese tragedy.
I could tell we were connecting more and more as Ella told me about moving to NYC, subletting, getting jobs, dating, etcetera. There was so much stuff to mine from the depths of a person’s life when you were just getting to know them. Discovery was the best part of meeting someone new.
We talked about music too — how there seemed to be a style coming out of North Carolina those days with bands like Old Crow Medicine Show and The Avett Brothers on the rise. She enjoyed a lot of music that fell into the “indie” category, such as Dr. Dog, who I also appreciated. In that minute, she told me that she was seeing them in September, had an extra ticket and invited me to go. Yes, definitely, yes. In reply, I invited her to see “The Dark Knight Rises“ in a few weeks with Mutual Friend Kevin and his girlfriend Dylan, for which we already had tickets. Ella was in!
This was awesome. I already knew of two more occasions on which I’d get to see her and that made me very happy.
“I’m gonna ask you something really random,” she said as she leaned in.
I felt like a child answering, “Hogwarts,” but it was true. I could not lie about my recent love for “Harry Potter.” She chose A Galaxy Far Far Away and I respected that as well. We briefly discussed the strengths of each choice (Cool castle versus spaceships) and then I said to her, “I want to be audacious.”
Ella laughed, smiled and leaned back in her chair. “Okay…!” she replied, wondering what the hell my incredibly vague statement had meant.
“Well…then…can I kiss you?” I asked.
“Yeah,” she answered, being super cute in the process.
I got a “husband’s bulge” almost as soon as we started kissing. (Just kidding — it took a minute.) But seriously, I was SO into it. We kissed and separated and smiled like the whole thing was a dumb joke. We then carried right on talking, as if to say, Well, that was nice! Moving on…
We talked a bit more, largely about “Back to the Future” and how the second one was the best, much like the “Mighty Ducks” trilogy. The conversation got me so heated up that I had to kiss her again. This time, it was a little heavier.
Then, a pause. I needed to pee. I got up to use the bathroom, but wouldn’t walk past Ella without kissing her again.
On my way back from the facilities, an Incubus song was playing on the speakers overhead, so I told her some story about Brandon Boyd, the lead singer, but she didn’t know who he was by name. So much for my cool rock star brag. It was okay — I didn’t think she expected me to be super cool anyway. I was sure that Mutual Friend Kevin had prepared Ella for what she was getting into. Apparently, they had been joking about the date beforehand and she told him that if she ended up seeing me naked, she would be sure to make fun of my microscopic penis. I laughed hard, but also considered that maybe I shouldn’t have been so open about my adolescent body issues.
Ella used the bathroom next and then informed that she had to talk to her landlord in the morning, so we had better get going. I saw that it was after 2:00 a.m and wondered how it had gotten so late.
On the way out of Oliver’s, I said to her, “Pretty convenient excuse you have not to go home with me. The whole landlord thing.”
Ella laughed, taking the joke appropriately.
“You live in Astoria!” she chided.
“Yeah! Why wouldn’t you want to end your night an hour from home?” I joked.
“I just talked to you about ‘Back to the Future’ — how easy do you think I am?!” she exclaimed and I lost it laughing.
We made it to the nearest subway station and partook in a final kiss or three. I told her that I would see her soon for the “Dark Knight” and I was excited because I knew it to be true.
Ninety-nine down and one to go. I don’t think this night could have been much better.
*In fact, I went back and looked at our texts and Ella had written “small dots.” I just read what I wanted to read and interpreted it as “small dogs.”
**I shot myself in the knee for writing this.
***I shot myself in the same knee again.