—Sunday, November 6, 2011—
Every so often, I would receive an email from an unknown woman, asking me to go on a date. In fact, by early November, I had already been on five dates with women who had unexpectedly emailed me. The difference with Ally was that even after reading through her first email to me, I still had no idea who she was. The author of the email was simply “100 First Dates”.
Though I did not know her name yet, I learned in that first email that Ally had a strikingly similar project to my own and that she found me by searching for “one hundred first dates” on Google. In addition to finding herself, she also found me, and understandably, she thought that we should go on a date.
I was wary at first, mainly because her initial email didn’t include any pictures, information about her or even a name, but a subsequent email cleared all that up and I readily agreed to go out with my female hundo-dating counterpart. I gave her a few options of dates to go on and she chose Walking Date, which I was very happy to do on this fine Sunday.
Although a walk was an active venture, it felt feeble considering that day was the day of the 2011 New York City Marathon, a portion of which I had watched in Long Island City. I’d gone to cheer on Alana, a woman I’d dated before the project began. She didn’t see me cheering for her, but such is my life.
And that was why I was roughly 30 minutes early to the Greenpoint intersection where I would be meeting Ally. LIC was just north of Greenpoint, so it had been a very quick trip. My good friend Kevin had been with me at the marathon and this date marked the second time in two days that I’d left Kevin, who was visiting from Boston, on his own so that I could go on a date. I knew he wouldn’t hold it against me, but just like the day before, I felt like a prick.
With 30 minutes to kill, I figured I could stand to be patient. If I had known Ally well enough, I would have called her and told her to hurry up because I was early. But I didn’t, so I waited, playing with my phone and people watching.
Walking and I had a generally positive relationship. I remembered walking to school as a child. Walking downtown to get a slush and some comic books from The Dugout. I used to love walking out to the mound to pitch. One time in Florence, Italy I walked all the way to Fiesole, which was kind of far.
More recently though, walking hadn’t been as fun. I aggravated both previously-injured ankles while walking around London two years earlier, so long distances got to me. I walked through Times Square on a regular basis, which was every New Yorker’s Hell on Earth. And my walk to the train each morning was always rushed because I was perpetually running late.
As such, I was looking forward to that day’s walk being a lovely and peaceful one — one that could restore my faith in taking a stroll.
Most often, I greeted people with a decidedly muted excitement, and meeting Ally was no different. I’m not sure why I have a hard time displaying excitement, but it seems that over the years I’ve developed a generally unenthused approach to first encounters. I can assure you though, that this meeting excited me. And also scared me. She was going to be writing about this, after all.
We discussed the recent craziness of the marathon and I pointed to the remnant rubbish in the otherwise empty street, which was still closed for the very last of the marathoners passing through.
Not wanting to be too controlling, but really because I didn’t know the area well, I asked where Ally would like to steer the Walking Date. In all fairness, she reminded me that this was my date and that I was in charge. We were up to two deferrals and a third would have been unreasonable, so I pointed us south towards Williamsburg, the only direction I thought I might find familiar.
My suggestion suggested that I didn’t really know where I was going, so Ally suggested walking along the water. It was a great idea because it’s always nice being near water and if we were feeling adventurous, we could walk across the Williamsburg Bridge. Secretly, I was very much hoping to walk over the bridge. However, I didn’t want to put any pressure on someone who may have been thinking she had only signed up for a 30 minute mom walk.
I learned that Ally was in improv classes at one of the same theaters I was studying at, which meant we actually knew some of the same people. It was not terribly surprising that this woman with a project much like my own also happened to be into the same artistic pursuit that I was, but it was a cool connection. And in the same community, nonetheless.
Following our discussion of all things improv, we talked dating, which had to come up sooner rather than later. Ally asked many of the questions I had grown accustomed to answering, like “What if you fall in love?” or “Have you been on bad dates?” To answer the first, I told her that I just tried to ignore it; that part of my goal was to stay out of a love. I didn’t mention her, but Julie came to my mind immediately when asked this question. Betsy too, for that matter. Even Pearl. I hadn’t seen either of them since our dates, but they had left quite the impression on me, that was for sure. The women of OHD were all too wonderful.
As for the subject of bad dates, I had no experience with those. Ally had been on almost 60 first dates in nearly two years and, predictably, many had been bad. I spoke to why I didn’t think I had bad dates. Specifically, that I blended well with others and that I usually tried to find something in everyone to relate to. I told her how I was susceptible to love or at least, relationships, and that I thought it had a great deal to do with desperation. At some point in my life, I had known what it was to be a desperate man (boy) and that sense of urgency, and the feeling that each chance was my last, those feelings never truly left me.
Ally commented that she was diving deep into my psyche. She summarized my thoughts, saying that I either needed or wanted a woman around at all times. She asked, to a certain extent, shouldn’t my mom be the one to take care of that desire?
This question was how I knew Ally hadn’t read too much of OHD. The Tattoo Date was my most read post at the time and I talked about my Mom being dead fairly often. I broke the news to Ally that my mom had passed and that, for several years at that point, I’d thought that my reliance on her had shifted to other women. It was something I was fairly aware of, luckily. She apologized for having brought it up, but I reassured her that it was totally fine. She really had dived fairly deep into my psyche though.
Ally’s probing only furthered the dating discussion. Why would someone choose to share that on a first date? How did one deal with with something like death if they’ve accidentally brought it up? We discussed the very concept of how to deal with saying or hearing something “bad” while on a date. It was not always easy to recover, but luckily for us, it was easy to forgive a stranger for not knowing that my mom was dead.
Talking more, it turned out that our relationship histories showed significant contrast. Whereas I had been in long-term affairs and remained friends with the majority of my exes, Ally’s relationships had been shorter and maybe less permanent in the end. She seemed to think, accurately enough, that my project was about staying single. As such, I wanted to know what her project was all about.
100 First Dates started because Ally had submerged herself in the world of online dating and friends constantly asked about her dates. She and a girlfriend kept a spreadsheet with information on all the guys so they could stay on top of things and to make sure they weren’t dating the same men. Eventually, her friends told her to start a blog so they could read about the adventures at their leisure and she followed their advice, launching 100 First Dates on the web in 2010.
Starting out slow and gaining momentum along the way, Ally had gone on 56 first dates in a span of nearly two years. She didn’t have a time constraint the way I did, but the greatest difference between our projects was that she was looking for someone throughout it. I was surprised she hadn’t found anyone, but unlike myself, who fell in love at every turn, she simply didn’t “like” people very often.
Ally and I were incredibly opposite in certain regards and yet we had such similar projects. It was almost hard to believe that we were on a date, especially one that I believed was going well.
Further down the waterfront, we stumbled upon the Brooklyn Flea. I wasn’t sure what it was at first, but Ally confirmed it was the Brooklyn Flea. I had only read about it on the internet and as we walked around a bit, I could understand what the hype was about. It was nothing extraordinary, but the goods there were certainly of a higher quality than most flea markets. We found a perfectly twee beverage vendor who sold Ally a fancy ginger iced lemonade and to me, a hot rosemary/honey/ginger drink.
We browsed the aisles, sipping on our drinks, and stopped at a watchmaker who seemed to specialize in pocket watches. There had been a brief period of my adolescence where I carried a pocket watch, as had my friend Ben, though he owned a much longer streak. I suppose I did it as a joke, but Ben’s use of one seemed to made sense somehow. I can’t think of why Ally needed to know this, but I told it to her anyway.
Leaving the market, I learned that Ally grew up in southern Connecticut, though I should have inferred that from her 203 area code. Upon mention that I had gone to college in Fairfield, I spurred a discussion on the value of education and how various schools were considered by employers, which of course led into another discussion on employment.
Over the years, I had often thought about working for a school or a non-profit, but I already recognized the inefficiencies present in many of them. I came to find out that Ally had spent ten years working for nonprofits. She knew first-hand how inefficient and “soft” they could be. It was encouraging to know that despite this tendency, she had found worthwhile and fulfilling work in the sector.
The Williamsburg Bridge loomed in front of us, and Ally asked me what I wanted to do about our walk. I got the sense that she didn’t particularly want to take the journey over the bridge, but I was kind of set on it, so I was a bit torn. I debated internally and eventually found the minimal courage needed to say that although I didn’t want to make her do anything she didn’t want to do, it would be cool to walk over the bridge. With hardly any hesitation, Ally agreed to it.
It’s scary how much this exchange sounds like most of my interactions in the bedroom.
Looping around to the entrance of the bridge, we headed up the pathway on the north side. I had never walked over any bridge in NYC, but earlier that week I had ridden my new bike to work (Queens > Manhattan) when the trains in Astoria had gone down. It was a bit of an adventure without a helmet or properly functioning brakes and I was glad I had survived it. Ally had previously ridden over the Williamsburg Bridge on her bike so I don’t think I impressed her with my story.
I was curious to know how long it took to feel at home in NYC and Ally said that after ten years, it was definitely home to her. That was good to hear because I could see myself living there for a long time as well. I really liked it. There was so much to do. So many people. I could only hope that this wasn’t some kind of short-term infatuation.
As we climbed the ever rising grade of the bridge, we took our first few pauses from conversation. I used to worry about these breaks much more, but after going on so many dates, I felt at ease with a few moments of silence, especially if they allowed both parties a chance to consider things, rather than have one blurt out a panicked string of words. As happens, we passed over the silence and carried on our conversation with relative ease.
Perhaps we were both pretty good at the whole dating thing.
For anyone who has not been on the Williamsburg Bridge, it would make a very good setting for an action sequence in a superhero movie. The subway runs down the middle of the bridge with the walkways straddling the tracks, just above. It would be pretty cool to see Spider-Man jumping over the path’s railing down onto a passing train, sticking to the roof of the car that the criminal is riding. Thoughts like this were only appreciated by certain people and to play it safe, I only mentioned to Ally that the setting would be cool for an action movie, and spared her the elaborate Spidey tale I’d written in my head.
We reached the other side of the river, but rather than go all the way down to street level, we turned around and went back to the ‘Burg. Ally gave me some grief for not fully completing the mission, but I liked the idea of being back in Brooklyn before dusk and she found my excuse suitable.
Talk of travel consumed us for the better part of the walk back and I learned that one of her favorite places in the world was in China, where she had taught English. In much the same way I felt about Italy, a piece of her heart would always be there, she told me. Recently though, she had begun a bit of a love affair with Spain, following her first visit. We found ourselves back on the other side of the bridge and I asked if she would like to have dinner or at the very least, a drink.
I never cut things off when they’re going well and it just didn’t seem like the date should have ended at that point, so I was being persistent.
Thankfully, Ally entertained the idea of dinner and she asked what I would like to eat. That slice of Brooklyn was her turf though, not mine, so I defaulted back to her. After some meandering, she asked if I like arepas, and although I had only had arepas once, on Silent Date, I told her that I did. As we approached a sign that read “Caracas”, I realized that it was actually the same restaurant as where I had gone on Silent Date, only in a different location. I’d ask what the chances were, that the only two arepas places I had been to were sister restaurants, but they were probably fairly high.
We were seated and given menus and specials. We ordered wine, split an appetizer and each selected an arepa. I noted the coincidence that the only two times I had ever had arepas had both been at a Caracas and both times with the only two women I had ever dated over the age of thirty. That would be one heck of a fun fact for the grandkids.
The topic of dating resurfaced as we discussed who should pay for a first date. In conjunction with other talking points, it was clear that Ally was a little more traditional that I was, but nothing so drastic that we completely clashed.
I admitted to Ally that I had been uncommonly nervous to meet her. I had expected a seasoned veteran, jaded by the dating game, and someone who would be able to sniff out my bullshit at any moment. She was very businesslike in her emails so I thought I was going to have to prove something to her. I assumed she would be nearly impossible to impress. In reality, Ally was kind, warm and very easy to get on with. The formality of a blog and of emails can make things seem so impersonal, so contractual, but really we were just humans trying to get together to make out.
That nervousness must have been the same nervousness many of the women who dated me felt when we first met. Dating a blogger was scary!
The food was great, as expected, and I enjoyed the wine as well. We split our bill as it would have been odd to do anything else after discussing my preference for going dutch.
We left the restaurant and I told Ally that I would walk her back to Greenpoint, where I could hop on a G train to go home. Shuffling north through Williamsburg, I pontificated on improv as a life philosophy, as I so often did. Everything about going with the flow and letting go of worries. Trusting my instincts had been a big part of OHD, but also my life over the previous seven years. From my mom’s death, I learned that the worst things could happen, but life carried on, and could even improve. Her passing and improv were so intertwined, and I was lucky that they were, because both of them together had taught me far more than either would have apart. If anyone had to hang out with me all the time, they would be sick of hearing about this shit.
Ally told me that we were on the longest first date she’d ever been on. I laughed but it was not the first time I had heard that from a date. The length, four hours, was roughly average for me, or maybe it was more the mean. I enjoyed long dates because it gave me more of a chance to make a good impression. If you gave it more time, you could get past the awkwardness and the “date stuff” and move on to some real shit all on the first date.
She said the fact that I got along with everyone and tried to see the best in people likely contributed to my penchant for long dates. That was true, I suppose. In the same way that I wanted time to make a good impression, I tried to give others the benefit of the doubt and plenty of opportunities to be themselves. I think the goal of a rich first date is uncovering the good stuff, fostering some sort of connection or at the very least, a little flirtation. It’s important to be aware that sometimes that which is worthwhile takes a little extra effort.
As we passed through McCarren Park, Ally walked towards the fence that lined the sidewalk and instructed me to follow. I was caught by surprise when she started kicking through the dried leaves on the ground. I followed along, reveling in the childish act, and kicking up some leaves of my own. I had thought she was pulling me aside to make out. What a dumb comment to make, but she forgave me for it.
Standing by the subway entrance, Ally asked me, as an interested dating blogger, how I usually ended my dates. She said she liked to hug but that she often felt overly awkward and ended up running away right afterward, or sometimes, didn’t even hug and simply walked away.
She wanted to know if I hugged, gave a firm hand shake or what.
I told her that I ended each and every single date with a kiss on the lips. A full on, serious kiss.
Ally didn’t believe me, so I insisted again that I kissed all my dates.
She was not buying it.
No, I admitted, I usually did something like what we were doing right then — where I waffle, looking for more things to say because I really don’t want to leave, and we both kind of look around awkwardly and make idle conversation until there’s either nothing left to talk about or I see a chance of something else happening.
“Oh, yeah?” she said, as we continued waffling, looking for something else to happen.
“Well, then what?” she asked.
I reached out my hands towards the pockets of her coat and said, “Well, then I do this and pull you towards me, and…we kiss.”
It was brief, but sustained enough to be serious, and pretty damn smooth if I do say do myself.
“Like that,” I said.
“Well that was very nice,” she replied.
“Yeah,” I agreed.
We wished each other a “goodnight” and I went down the stairs to catch my train home. Once I was above ground again, we exchanged a few text messages and the night drew to a close.
Read Ally’s version of our date over at 100 First Dates.