Stargazing Date

—Tuesday, August 30, 2011—

This is a tale of enemies turned lovers.

I texted Madelyn to tell her I was running a few minutes late and she replied that she was sitting at a yellow table under a sculpture of a cartoon mouse. As I approached The Standard Hotel, I saw what she was talking about: a giant gray sculpture of a very glum looking cartoon mouse sat outside the entrance. It was certainly a good meeting place, as I saw many other groups of people gathering there.

Stargazing Date 1

Madelyn stood and greeted me with a hug and a kiss. We looked like any other couple meeting up after work. You wouldn’t have had any idea that it was our first official date.

She was wearing snappy cut off shorts and a casual striped top. She looked incredibly cute. I was so lucky with the women I had the opportunity to date during this project, in regards to both personality and appearance, and Madelyn was no exception.

One might wonder why Madelyn so readily kissed me. It was simple really: we had kissed before. Somewhat recently, in fact. Still though, there was something remarkable in the action, for Madelyn was One Hundred Dates’ first major opponent.

Back in May of 2011, when OHD was still just an idea, Madelyn had come to one of my improv shows with a couple mutual friends. Although we had both attended the same college, I’d never met her before that night at a bar after the show. I had been telling my friends about the concept for OHD and by the time I began listing some of the dates, Madelyn spoke up.

She flat out told me it was stupid. A woman would feel unimportant to be the Coffee Date after reading about my Fancy Dinner Date, she said. She insisted that I would be perpetuating the stereotype that men in New York have their pick of the women and won’t settle down unless forced to do so.

No one I had talked to had been so critical. I had plenty of people voice their concerns, for myself and my dates, but no one had hated the project outright — or at least they hadn’t vocalized it.

Prior to her objection, I’d been hoping to impress Madelyn, maybe make her laugh, so that I could eventually ask her out. After all, she was very cute and we knew some of the same people. After speaking out against the project though, I was determined to get a date with her. I told myself that she’d have to come around after the project began. I had faith that OHD would be likable and sincere, and that with enough pestering, I could break her down. As the project began, I put Madelyn in the back of my mind, knowing that I’d have to prove myself first.

Just over a month into OHD, I received a question on my tumblr reading:

“No question here…just a fan of your blog. I met you after an improv show a month or two ago with my friend Angela. Not sure if you remember but I gave you a pretty hard time about this project. I recently remembered that conversation and decided to check your blog and…….I LOVE IT! So much fun to read that I am actually laughing out loud at my desk. Keep up the good work! I hope there will be a book soon :)”

I immediately emailed our mutual friend Danny for Madelyn’s contact information and emailed her that same day. Although she originally only wanted to play matchmaker (she found me my College Girl Date), I convinced her to go on a date with me by the end of that week.

By that Saturday, I was getting text messages to meet up in the West Village, and although I couldn’t make it that night, only five days later, I met up with Madelyn for drinks after a rehearsal. She’d texted me earlier in the day saying she had dressed up to go out and her plans cancelled, so I was her back up. In fact, she has contacted all her other friends by that point and I was her last resort.

I’ll take last resort any day. No foolish pride here.

After a drink or two, Madelyn laid one on me. She said it was a ‘thank you’ for meeting up with her on short notice and for making sure she had not been dressed up for no reason. We kissed some more until the boys at the table next to us began hooting and hollering. That was our cue to leave. Madelyn walked me to my subway stop, and after some more kissing, the halal cart several feet away began playing Celine Dion’s My Heart Will Go On. Nothing is quite as romantic as a cart-side slow dance on an NYC sidewalk to end the night.

We met up once more for drinks and karaoke a couple weeks later, having a great time getting drunk and singing our hearts out. Plus, we made out way more and she didn’t give me shit for singing the Moulin Rouge! version of Your Song.

Getting a date with Madelyn was the biggest success story of OHD up to that point. It spoke to the power of conviction, the goodhearted nature of the project and the humor that came across in the writing. Even before we had began our official date, I felt like the comeback kid.

As Kevin Garnett said, anything is possible.

Dusk wouldn’t set in for another hour, so we made our way to the The Biergarten for drinks and an over-sized pretzel. Since Madelyn was a fan of OHD, we talked about the project extensively at first. She poked fun at me for making out with a lot of girls. To be fair, if you included Madelyn, I had kissed 9 out of 17 women thus far and though she wouldn’t have known it, there were two others I’d kissed and hadn’t even gone out with yet. So, I was a bit of a kissing bandit early on and felt a twinge of guilt over being called out on it.

We debated whether it was better to be doing what I was doing publicly or privately. It seemed to be that there was a benefit to having everyone actually know what was going on. Many people dated around without ever making it clear to their partners that they were not looking for a relationship. I think what I was doing at least had a high degree of transparency, but the openness was both a blessing and a curse, Madelyn said. It was great to be honest about intentions, but if someone had been interested in me, it would have been painful to see my exploits strewn across the internet. Even if it was mostly innocent kisses.

In the midst of that conversation, I thought of Alana, the woman I’d been dating before OHD began. I’ll save the full story for another post, but suffice it to say that when I first met Madelyn, I was seeing Alana on a fairly regular basis. We got involved with each other after the wheels of OHD were already in motion, and although I cared about her, I wouldn’t give up on my plan to date a hundred other women.

To say that she was upset with me would be an understatement. Every time I wrote a post where I described feelings for another woman, or mentioned that I’d kissed someone, I felt Alana’s eyes on me. They never wore a look of approval. Even now, writing years later, I can’t escape the guilt I feel over hurting Alana and making a public display of it all.

Madelyn doubted we would have much to talk about since she knew everything about me from my previous writings but she failed to realize that I didn’t know very much about her. Also, I didn’t write about everything discussed on my dates, I told her.

I really wanted to get past that part of the date. The part where it felt like we were only there because of the project. That wasn’t the feeling of the last two times we’d hung out and I didn’t want it to be that way for our official date. We needed to turn the corner and make it genuine. I knew we could do it, we just needed an opportunity.

After standing for nearly 10 minutes, two seats finally opened up and I offered to hold down the fort while Madelyn retrieved her pretzel. She kindly told me that she would much prefer if I’d get the pretzel for her. I was wary of being unnecessarily chivalrous, especially since we already knew each other, so I actually liked that Madelyn nudged me to be a gentleman. It was what I would have done had we not already been so friendly.

Upon my return, we got onto the subject of Facebook and the adults that used it. This was prime time to mention that I’d recently become FB friends with my father. Since my dad was now an Internet pro, I mentioned that I had been very careful not to throw him under the bus when writing for OHD. After all, I talked about some fairly serious personal things on the site and my sometimes strained relationship with my father would likely seep through if I allowed it to. But he didn’t deserve that. I did love him, after all. He was just…eh…another time.

Madelyn understood completely, living through a less than pleasant relationship with her father as well. We began talking about our families and there was a moment when I saw the change. We were suddenly on an honest date. As we talked, the project faded from both our minds and we effortlessly related to one another. The project was sure to come back around, but those first moments of forgetting about it were really nice.

I recounted to her, from my perspective, the events of the March 11th tsunami in Japan: finding out about it as I arrived at work and immediately taking to the Internet to find out if my aunt and uncle in Tokyo were safe. I told her how much I worried that day, even after finding out they were all right. Even after I called the rest of my family to tell them Haruko and Kelley were fine, I remained shaken up and emotional the entire morning.

As I told this to Madelyn, I could feel myself starting to tear up. Oh God, please don’t cry, I thought. I was not looking for sympathy. Luckily, the conversation passed and the tears remained at bay.

We talked for a while longer, and as the sun began to set, we headed up the closest set of stairs to The High Line park. We watched the second half of the sunset over the Hudson River from the western side of the park, leaning up against the rail. The Amateur Astronomers Association of New York was setting up, as they did every Tuesday night, and there were four or five telescopes out already. We talked until the sun had vanished beyond the horizon and then settled into a reclining wooden chair nearby.

The High Line was an incredible little park. It was my first time up there and I loved it. The design of those chairs we sat in, on rails allowing them to slide apart and together, was both very creative and highly functional. I was a fan.

We sat, Madelyn’s legs laid over mine, and watched the stars as they began to appear. I heard about her post-grad days and we swapped life stories. Weddings, families and friends. Eventually, one of the amateur astronomers made a last call for the viewing of Saturn. We pulled ourselves up and walked over to his telescope to view Saturn just over the horizon, mere minutes before it disappeared.

As we waited for our turn, a woman walking by enthusiastically answered the astronomer’s invitation of, “Would you like to see Saturn tonight?” with “Of course we do!!” I told Madelyn that I wish I lived life more like that — jumping into experiences with unquestioning enthusiasm. She thought I did an okay job of that already and she wasn’t totally wrong. But, for all I preached about living in the moment, I worried a lot and second guessed everything all the time.

I was about to burst, I had to pee so badly, so we went back down to use The Standard’s bathroom. I loved the layout of the bathroom, how the male and female sides were only separated by a chain curtain. It was equalizing. Everybody poops, you know?

On our way back upstairs, we made a pit stop at the photo booth. There’s no way I can pass up a photo booth opportunity on a date. Smiles. Kissing my cheek. Kissing each other. Stupid faces. All in all, a wonderfully adorable experience. (The pictures in your mind with have to suffice, in order to protect Madelyn’s secret identity [j/k—she’s Sigourney Weaver].)

We walked back outside and to the beginning of The Highline, purchasing cones of organic ice cream on the way, courtesy of Madelyn. As we walked along the narrow park, we swapped our most outlandish sexual escapades. I said that the bathroom shenanigans of my Brunch Date had been out of step for me.  I know that making out in a bathroom isn’t that crazy, but it was atypical public behavior given my track record. We’re talking about a kid that had only had sex in a motor vehicle once, and I was 24 when that happened.

Madelyn seemed a bit surprised that I had so few sexual exploits, so I told her how I had been shy about public affection when I was younger. In fact, I was uncomfortable with sexual matters and my body as a young teen. Like most teens, I suppose. Not only had I been malnourished looking, but I went through puberty fairly late, so that always made me feel even more inadequate. Pretty cool stuff to brag about while on a date at the age of 25.

We continued walking up The High Line and passed by the astronomers again, then in a different location, waiting for Jupiter to rise. We planted ourselves on the tiered rows of seats in front of the glass window at 17th Street, looking up 10th Avenue, and finished our ice cream. We remained seated there for some time, talking about our jobs and our families. We both wished that location had had a stage or a movie screen. It would have been a really good spot to catch a show.

As we walked further north, we passed by a pristine, grass covered area. All I wanted to do was lay down on it, but it was roped off and park rangers were nearby. Madelyn encouraged me to live dangerously and so we stepped over the rope and laid down.

The grass beneath our backs was perfect and the view was incredible. The stars shined above us while our peripheral vision was crowded by skyscrapers — a truly New York experience. I was starting to worry about being on the grass and wanted to get a move on. Madelyn rolled over and kissed me. I forgot about my anxiety for a moment and then we hopped up, back over the rope and carried on our way.

It was really something, strolling right past those large apartment buildings that bordered the park, seemingly close enough to jump through their windows. It was an absolutely beautiful evening to wander through a park. We arrived at the glowing frame of a billboard at 26th Street, which begged for a photo op.

Despite the number of selfies taken for this project, I am generally reluctant to having my picture taken, but Madelyn said that the picture of me was the best part of each post. Since she put it so nicely, I decided I had better get a picture. It was also her comment that made me realize I should take my picture before every date. We sat there for a few minutes afterward, looking through the billboard frame and laughing at tourists.

Stargazing Date 2

Further up the path, I saw people walking back from seeing Sleep No More, my favorite theatrical production ever. I told Madelyn a bit about the imaginative retelling of Macbeth and what I loved about it. It was an immersive theater experience, which gave one the feeling of walking through a dream. I’d recommend it to anyone with a love of theater or a sense of adventure. Seriously, it makes me want to cum.

We were discussing Senior Week* stories and other college antics as we reached the end of the line. We turned around, walking back south, and after a minute or so, there was no one coming towards us from either direction.

Literally, the path was clear. I pulled Madelyn towards me and kissed her long and hard in the middle of the walkway. We didn’t release until people were once again upon us. Sometimes a good kiss deserves a good laugh, and we both giggled as we held hands and continued walking.

Madelyn told me that we needed to dance again, referring to our spontaneous Celine Dion moment from our first outing. The gears in my head immediately began to turn. As we walked, I looked for a secluded spot until finally I saw one near the grassy knoll we had previous laid down upon. I led the way, Madelyn in tow, and once there, asked her to wait a moment.

I took out my iPod and queued up some Otis Redding. I put one bud in my ear and handed the other to Madelyn. I pressed play, took her hand in mine, slid my arm around her waist and pulled her towards me.

In case you’re wondering, These Arms is a near perfect song to slow dance to on a beautiful summer’s night. As the second song began, our lips found each others’ once again.

The whole experience was absolutely lovely. I’d been wanting to do something that cheesy and romantic for a long time and it felt good to act on the impulse.

Between dancing that night, the fireworks-backed kiss a week or so earlier, the various rendezvous with Ariana and the signs I’d held up silently while waiting for one date, August was rounding out to be fairly romantic.

We’d stargazed, we’d walked, we’d danced and we’d kissed. I supposed it was time for a late dinner.

Madelyn and I walked to find food, talking a bit about past exploits once again, until I asked her how she had become friends with Angela, the friend responsible for us meeting initially. Just like any good relationship, there was a funny story behind how they came to be best friends, which she told to me as we walked the streets.

We found ourselves a sparsely populated restaurant and were seated in a booth far from everyone else. Madelyn read my mind and asked if I wanted to share one side of the table. Of course I did! I used to hate sitting on the same side of the booth as my date, but then I had a girlfriend whose request I couldn’t turn down, and ever since then I’d been a convert to same-side dining.

Continuing our previous conversation, we discussed our different freshman year experiences at Fairfield. We ordered our food and kept the college conversation rolling. Our meals came out quickly and we found ourselves talking about tattoos.

I described to Madelyn the tattoo I’d be getting in a few weeks. I told her about the significance of the design, which related heavily to loss. I mentioned suicided and remembered that I had recently lost a great uncle to suicide. It had escaped my mind for a while, but it was only a few short weeks earlier. Since Madelyn worked as an art therapist among the geriatric population, she told me about the different ways they aged and dealt with, or rejected, death.

Madelyn was heading to the Upper East Side and I somehow needed to get myself to Queens. Of course, I wanted desperately to go home with her, but it wasn’t in the cards that night. Little did I know then, but it would never be in the cards again. I haven’t so much as seen Madelyn since that night.

She rode the L train across town with me so I could pick up the N/Q.  I felt bad for keeping her up late but it had been such a good night, I doubted she was be too upset with me.

As our train pulled into Union Square, I gave Madelyn one final kiss goodnight and hopped off to make the rest of my journey home.

*Senior Week — An annual Fairfield University tradition in which the seniors stay at school for an extra week between exams and graduation, attending various social events where the primary goal is to drink a lot, reinforce lifelong friendships and burn bridges with all haters.