—Tuesday, June 26, 2012—
If you’re having girl problems I feel bad for you son, I got 99 problems but a mom ain’t one. In fact, this mom was the opposite of a problem — she was my 100th date!
For all the preparation I’d done throughout the year, it was actually kind of unnerving that this date had only become a reality the day prior. Monica was the girlfriend of my co-worker Phil, and she had suggested her boss, Anna, for Mom Date earlier in the month. However, I didn’t take her up on the offer right away because I had other potential dates from OkCupid that I was already interested in. I thanked Monica for the suggestion, but told her to hold off.
A few weeks passed and, over the weekend that preceded this date, it became clear that I wouldn’t hear back from any of my OkC prospects, so I decided to reach out to Monica — via Phil — for help. [In one way or another, this was the fourth date that Monica was responsible for!]
That Monday, I was given Anna’s email address and the expectation that she’d be a willing participant. I emailed her right away and though she told me that she was wary of being a guinea pig, knowing that she would be the 100th date had convinced her to partake. An email or two later, and I had my final date of this goddamn project all lined up.
Since it was my 100th date, Anna wanted to do something that I normally wouldn’t have done, something different than all the other dates. Since we worked within the same two block radius outside of Times Square, I threw out a few ideas for terrible Times Square activities and Dave & Buster’s was quickly decided upon. I couldn’t believe that I was taking a significantly older, single mother — who was the boss of a friend of mine — to Dave & Buster’s for my 100th date.
Or maybe I could. Very little surprised me those days. And this was actually the second mom I’d been out with, if we wanted to be technical about it, with my Older Woman Date being the first.
As I walked out of my building at the end of the day, even as I rode the elevator down to the hobby, I was beaming. So much visible happiness from me was about as common as a well thought out defense of America’s handgun laws [Nailed it]. I was so excited that this would be my last date. I was so excited that I had made it this far. Please, dear Lord I do not believe in, do not let Anna cancel on me last-minute.
I hustled through the Times Square crowd with an uncharacteristic skip in my step, completely unfazed by the horrible creatures that surrounded me. By the time I got to D&B, I’d received a few congratulatory texts from friends and past dates, plus a bevy of Instagram and Twitter notifications. [For me, a bevy was equal to anything more than three.]
Standing on the south side of 42nd Street, surrounded by the likes of Madame Tussauds, Modell’s, BB King Blues Club and Applebee’s, I was only left waiting for a few minutes before my mom appeared in front of me. [I obviously don’t mean my real mom because she was super dead and, despite all the recent zombie scares, she had not risen.]
Anna — my Mom Date and official 100th date — arrived with a burst of energy. I gave her a quick hug but she seemed eager to get this thing going. I loved a woman with enthusiasm! We walked inside and I told her I’d never been to D&B and probably hadn’t been to an arcade of this kind this since I was a kid. Anna had a leg up on me in that regard because she occasionally went to a D&B near her home with her five year-old son. I laughed to myself. I was literally taking this woman to do something that she only ever did with her child. Mom Date, indeed!
On our way up the escalator, she double-checked, “So this is the 100th date, right?” It sure was, I confirmed. “So what are the other dates you’ve gone on?” she followed up. All of them? Oh jeez. I tried to think of some interesting date themes to rattle off but I didn’t come up with very much. Instead, I just told her about some recent ones. She asked for a favorite, but I didn’t have one! Rather, I told her that I’d gotten to do a lot of cool stuff in NYC and had met a ton of awesome people — both things that were overwhelmingly true. Based on the escalator ride alone, I got the feeling that this date might end up being a recap of all 100 dates in some kind of unplanned, final episode sort of way.
We made it upstairs to D&B and, like a flower in the wind, Anna sailed right into the game room while I followed behind as best I could. There was no conversation about potential drinks or food, only pure enthusiasm for playing arcade games.
To be honest, I got the sense that maybe Anna wanted to just get the date over with, and not because she was a jerk, but maybe because she was anxious, nervous or simply trying to be helpful! I wasn’t sure, but her attitude did make diving into our date incredibly easy and I was grateful for it. We bought a $25 Power Card with something called Turbo Charge for $3 extra, which Anna explained was like a super-sizing a value meal. Awesome. I liked that idea. She also mentioned that her son enjoyed the coin pusher games most because they were easy and he could get a lot of tickets from them. That’s right! Tickets! I had kind of forgotten that tickets were a part of the arcade experience.
With our Power Card in hand, we hit the game floor with one major question: What did we want to play?? Our first game was skee-ball — which we played a few rounds of, splitting it two games to one — and we chatted a bit while we played. Anna was born and raised in Scarsdale, NY (Just north of the city in Westchester County), but had also lived in NYC for years before she got married in her thirties and moved back to the suburbs.
We moved on from skee-ball and found a Terminator Salvation shoot ‘em up game that seemed like it had a ton of stuff going on as we played it. Anna was very comfortable mentioning her son, and had already done so a number of times, which was a stark contrast to the only other mother I had dated, who barely mentioned her children at all. Contrast aside, I really didn’t mind that she frequently mentioned her son. That was par for the course, wasn’t it?
Though this date had been set up by someone who worked for Anna, I didn’t really know what exactly she did, so I asked her about it as we checked out the Wheel of Fortune game. She was involved in some kind of fashion design or production, I can’t remember which. We won a round of Wheel of Fortune, but the game was a total rip off, because it told us to add more money in order continue. We’d won! What the hell? Screw Wheel of Fortune, man.
Along the way, I also learned that Anna was still technically married. Separated, but married. In addition to being the second mother I’d gone out with, this also made her the second married woman I’d dated. Crazy.
We waited for a basketball shooting game for a while, but it was too crowded and no one was letting us into the side-by-side lanes, so we cut our losses and moved on. We milled around a bit before playing a few more games — head-to-head Ms. Pac-Man, a wheel spinning game and, after searching without luck for Whac-a-Mole, we played something NASCAR themed. Finally, we played an Ice Age game called “Ice Breaker,” which was super stupid.
Our pace slowed down a bit, which was probably good after running around for a while, and we decided to hit up the basketball again. This time, there was no one in our way and we were able to get to the hoops. We got a few games in before Anna suggested we grab a beer and that sounded perfect to me.
As had happened many times that night with the popular arcade games, two people swept in and took away the pair of seats we’d been eyeing at the bar. As such, we went around to the back side of the bar and found two stools. It ended up being better though, since it was bit quieter back there. We saddled up and Anna ordered a Blue Moon while I got a Budweiser. There were trays of unnaturally colorful salt, intended for all kinds of gross cocktails, set out in front of us. This place was so delightfully tacky.
Over beers, Anna and I talked for a long while. She told me that she had gone to FIT for school and that she could remember a time when Times Square was a place that guys would go to pay for blowjobs. She also told me more specifically what she did for work and about her upcoming trip to Asia with Monica, which would involve some factory visits. They worked particularly in knitwear which, contrary to my initial thoughts, did not mean sweaters.
Anna mentioned that she had no filter on what she said to people and told me how she didn’t really censor her son either. He would say “sex,” “boobies” and all that stuff in public and it would get them both in trouble sometimes. She shook it off though. She was a hippie at heart and claimed that people needed to chill out. I definitely got the sense that Anna was very easy-going and I could see how that might translate to her son. She was enthusiastic too, which I appreciated. I told her that my parents hadn’t censored my brother or I too much either, but they’d probably been a little less free-spirited than Anna to being with.
I told her a little about where I was from and, when she asked if my parents still lived there, I explained to her that my mom had died but that my brother lived near my father. I talked more about my family and addressed some recent concerns with my grandmother’s health. I wanted to go out to California and see her before our annual Christmas trip, but didn’t want to jump the gun. Anna agreed that maybe I should. [I eventually did take a preemptive trip to see my grandmother and it ended up being the last time I saw her alive. I was glad I’d followed Anna’s advice.]
She asked me more about the project, so we spent some time discussing that. She tried to think of dates she would want to go on and, as she listed ideas, I told her that I had done most of them. Travel? Yup. Breakfast? Yeah. Sleepover? No, but I had considered it. Tattoo? You know it. I showed her my tattoo and explained the meaning of it. As both a mother and daughter, Anna understood why losing my mom had been so life-changing and she thought my tattoo was really cool. She was impressed that I’d gotten it on a date and said that she wanted to do that too — something cool to spice it up.
I also told Anna about my Older Woman Date, Lois, and joked that, as the second oldest woman I’d dated (Anna was 41; Lois was 45) and with only one kid (Lois had two), she had nothing on her. It was a playful moment.
Anna told me that she still lived in her house with her husband, although they didn’t like each other any longer. She waxed poetic about meeting him in her early 30s, marrying him only a year later, having a kid and essentially jumping into everything, which in retrospect was less ideal and magical. I asked if the whole biological clock thing actually had an effect on women in their 30s and she said that it was huge. So many women at that age settled for some subpar man or subpar relationship simply because they wanted to have kids. She said that in vitro fertilization (IVF) was great though for that reason though. It was a huge business and lines were out the door. More women could have kids later in life or without men altogether.
I also got to hear about Anna’s group of friends from her daily Metro-North commutes, which sounded like such an adult thing to even have. There at the bar, we became Facebook friends so she could show me pictures of her son and, after she mentioned how she liked to keep his hair cut long, I showed her pictures from back in college of when I’d had long hair.
We talked about cheating and sex for a while, which was very interesting. Anna told me that her husband was always “going out with Jim” every night of the week. She knew it was another woman and that was fine, she asserted, but why bullshit about it? They were separated, after all. She went on about cheating for a while and said how everyone in the suburbs around her age seemed to do it. I told her about “The Monogamy Gap,” which I had recently read, and she said that it all sounded pretty spot on.
The talk also included discussion on sexual and emotional satisfaction over time and, as someone who had way more experience than I did, it was great to hear Anna’s opinions on such matters. She was very free and forthright in that regard — very open minded — but she knew that not every one was.
As a cap to the D&B experience, we played a few games on the MegaTouch machine sitting to our right. Photo Hunt, Play4 Crossword and Word Dojo used up our last 23 credits and then it was over to the arcade store to claim our prizes. Our 318 tickets wasn’t going to get us very much, we realized, but we managed to snag two hedgehog erasers and then gave the rest of our tickets to a mom with a little boy. It was perfect. This was so great and so fun.
Debating where we should eat dinner in Times Square, Anna suggested Ruby Foo’s, which was practically across the street from my office. This whole date was hilarious to me, but I was more than on board with her suggestion. Anna took my arm as we left D&B and we walked through the crowd, talking about how weird Times Square was and how it was odd that the Naked Cowboy even existed. We walked arm in arm all the way to Ruby Foo’s and it was after 10 p.m by the time we sat down.
Making quick work of the menu, we ordered some dumplings as an appetizer and then both selected sushi rolls as entrees. We also made sure to have some green tea. It was fun.
Over dinner, we talked about hooking up in the suburbs, especially amongst those that cheated, and she said that it reminded her of sneaking around when she was in high school. People might use their parents’ vacant homes while they were out of town, or a vacation house or hotel, to hook up with their lovers. It had confounded me earlier, where these people would go to do this stuff when everyone had children and lived in fairly close communities, so it was fun to hear about their creative solutions.
It was funny to talk with Anna about this stuff — she had a way of making everything seem like it was all just a part of life and that everyone rolled with the punches.
I spoke to her briefly about being stuck between places in life, as I was at the time, and about being a Jack-of-all-trades, but master of none. She said that it was okay for me to feel stuck and that I would get used to it eventually. We also discussed the comfort of actually having a job and paying bills. She told me that her greatest worry in life was money and a lot of it seemed to have to do with the high cost of living where she lived and having a son. Yeah, money would worry me too, in that case. I could remember my mother constantly worrying about money, growing up.
Our meal drew to a close and we were brought our fortune cookies. I cracked mine open and the small piece of paper inside read, “The person who will not stand for something will fall for anything.” That was how I felt most of the time in regards to romance and dating. I’d never had a particular thing I was looking for and I had therefor fallen for just about anything. It was fitting to fine this note at the end of a project which had been designed, in part, to give me some direction in what I looked for in a partner and to make me more selective about falling in love.
Anna threw down cash for more than half of the bill and when I told her that was silly, she calmly said, “I’ve got more than you.” I couldn’t argue with that logic. I knew that I had done the same many times before over the course of the year and I appreciated her doing it for me now.
Leaving Ruby Foo’s, Anna offered to walk with me to my subway stop, which was only a block away. At the entrance to the N/R/Q at 49th Street, I gave Anna a hug and a kiss goodnight, which felt far more celebratory than romantic.
With that gesture, I WAS DONE.
On the train ride back to Queens, I shuffled through my phone’s limited music selection, looking for music to properly satisfy my desire to dance. Back in Astoria, I hopped off of the train, blasted Robyn’s “Dancing on My Own” and pranced all the way across Hoyt Playground, throwing my arms up in the air like I was the champion of the world.
I wasn’t the champion of anything though, just a hundred dates and a year of my life I was sure I’d never forget.