Ex-Girlfriend Date

—Friday, April 13, 2012—

It had been just over nine months since Alana and I had seen each other. Nine months since I stood on her stoop, returning a book I’d borrowed. Nine months since I’d apologized over and over again for having to start this project and for having to break things off with her. Alana was the last woman in my life before I started OHD, and though our relationship was heavy at times, I couldn’t have picked a better ex to take on this date.

IMG_1962For the record, we were never boyfriend/girlfriend, but we were headed down that road. We were dating and sleeping together and being good to one another. She knew about the project the first night we hooked up and though she never imagined it would be factor in her life, it became a pretty big one after we started seeing each other regularly. She didn’t anticipate actually liking me. I didn’t anticipate liking her either.

The seeds for OHD had already been laid though. I’d told friends I was going to do it. I’d told myself I needed the experience. And hell, I’d launched a website for it. So, I had to carry on, even if I was simultaneously falling for Alana.

OHD was what made me so conflicted about ending our relationship. This project was the reason she was hurt. It was the reason she cut me off for several months. Well, let’s call a spade a spade: Those things were my fault. I was the project. The project was me. I could have called it off. I could have made us work. But I didn’t.

Fortunately, we reconnected, slowly, over the Autumn of 2011. As Alana prepared to run the NYC Marathon, I continued to support her because she needed support and she deserved it for all the hard work she had put in. She had just started training when we first got together. I had just started the OHD journey at the same time. The previous nine months had been insane for us both.

Alana ran that marathon in support of The Leukemia & Lymphoma Society and I had donated to the cause early on. She insisted that I didn’t need to donate simply because we were dating, but I told her that I liked to pay it forward. Who knew when I would need something from them?

As it turned out, I had made a wise investment, because in early October 2011, my father was diagnosed with (a minor case of) lymphoma. Although Alana and I weren’t speaking much at that time, one of the first text messages I sent after receiving the news was to her, thanking her for running the marathon with Team In Training, because now my father would need that support. From then on, I became even more supportive of her training and she, in turn, checked in on me regularly to see how my father was doing. She dedicated a mile to him. She wrote his name on her arm. She put aside our past in the name of something more important.

Alana also knew what my mom’s death had meant to me. She saw the potential for my dad’s death to compound that pain and she made sure, as others had done, that I wasn’t alone. This was after I’d left her. After I’d been the selfish twenty-something that I was, Alana looked out for me. It spoke volumes to who she was as a person. She was a beautiful person.

Once we were back on good terms and we had more or less reconciled, she mentioned the idea of a date. I was both amazed and thrilled. Then, she ended up with a boyfriend for a few months. But when that ended about a month before this date, she reached out to me again, saying with enthusiasm that she’d like to go out again. I had been very much looking forward to this day since then.

As such, I was fairly nervous. The place we were going, Malatesta, was supposedly quite popular and didn’t take reservations for two, so I was sure we’d have a bit of a wait. It was Friday night, after all. Friday the 13th, to be exact. It was only the second Friday the 13th of the year and I’d had dates on both of them.

Alana had mentioned towards the end of the work day that she was very hungry and very thirsty, so as I left my office building, I stopped and grabbed a couple granola bars and a bottle of water for her. I didn’t want her getting grumpy if we had to wait a long time.

I then ran to the flower stand by my building, because, shit, I just really wanted to have flowers for her. I wanted a nice, romantic gesture to start off the evening. Plus, I was encouraged by the recent flowers I had bought for my Celebrity Date. It was a little different though — that was Broadway and flowers were a part of the deal. Flowers for Alana would be more personal.

Regardless, I spent five minutes or so debating flowers but ultimately decided that it would be awkward for her to carry the bouquet, or whatever, so I didn’t buy anything. I also didn’t know what kind of flowers she liked. I got on the train and went down to the West Village.

I passed yet another flower stand on my walk to the restaurant but couldn’t decide upon anything that would be simultaneously unobtrusive and pretty, so I gave up on flowers.

Arriving at Malatesta, I knew I was significantly ahead of Alana, so I waited patiently. As I lingered, I noticed that the staff was actually Italian, and speaking Italian a good deal, even to the English speaking customers. The place looked great. Also, it was not very busy yet, so I knew we’d be seated. I wouldn’t need the goodie bag I’d brought.

My nerves cooled as I waited for Alana. I think I’m going to be fine.

Alana texted to say she would be there shortly and that she had just seen Ted Allen on the street. I looked up Ted Allen and responded, “Cool!” When I saw another text, asking where I was, I rounded the corner of the restaurant but didn’t see her. I questioned myself as though maybe I had accidentally told her the wrong place, but I didn’t think so. Soon enough, as I was replying, Alana emerged from behind a group of flamboyantly dressed characters, smiling bright. She apologized, but she had been stuck behind a “tranny” for her whole walk. Humorous, as usual.

We hugged. It was good to see her. It was a little bit awkward. I could tell that she was nervous.

Alana had to be one of the more confident people that I knew. It was one of the things that drew me to her initially. Over the first 15 minutes though, it was obvious that she was not her confident self. It was odd to see her off her game. I wondered if this was all a bad idea, like maybe I’d forced this date when I should have let our sleeping romance lie. I wondered if Alana had had to psyche herself up for the date, telling herself that it would be fine, but once that were there, perhaps she felt too many emotions flooding back. I know that I was feeling like that to some extent.

As we discussed the menu, Alana was shaking ever so slightly. Between her nerves and my worries that I had put us in a disastrous situation, the start of the date was a bit awkward, but we loosened up soon enough.

We caught each other up on life things. Alana asked about my new improv team. I asked her about her new job. She had been given a lot more power than she had initially thought, going into it, so that was cool. However, she hadn’t had a great day because work was stressing her out. She was a content manager for a website and had been dealing with idiot writers all day, though she was able to give me examples from the “How to Get Beyoncé’s Look” piece that she’d come across, which had actually brightened her day a bit.

Addressing the elephant in the room, Alana asked if I was glad that OHD would be over soon. Indeed, I was happy to have the end in sight and her question reminded me of something. I took out my phone, brought up my calendar and showed Alana the calendar appointment I had made the previous June, when we’d gone our separate ways. It was for July 1st, 2012 — the day after the project ended — and it read, “CALL [ALANA] AND ASK HER ON A DATE.” She laughed. She liked that it was there. I liked it too.

The thing is, though I had presented it as a joke to her, I was pretty serious when I’d created it. Over the previous nine months, I had looked at it time and time again, never deleting it from my calendar. There was still a part of me which very much wanted to call her on July 1st and ask her out. There was a part of me that wanted her to wait a year for me to do my own thing and then welcome me back with open arms. It was a long con that had very little hope of ever paying off, primarily because I was a selfish idiot. In my defense though, I was driven by a very real love for Alana. I’d grown to love her, and maybe I wasn’t sure yet what kind of love it was, but I knew that I wanted her in my life. That was for sure.

We ordered a piadina to start, which I had never had, but was like an Italian quesadilla with mozzarella, prosciutto and some other goodness. It was great.

Alana had been reading Fifty Shades of Grey which I thought was Twilight fan fiction for some reason, but we couldn’t confirm that without looking it up, which we resisted. (As it turned out, I had been right, but I don’t remember where I had heard that information.) She told me that it was funny to be reading an erotic book on the PATH train every day, but that she was not embarrassed. Everyone was reading that garbage, so it wasn’t abnormal or anything.

The food was really great. I don’t recall what each of us ate, but those details were pretty insignificant to this particular date. All I remember about it was that it was delicious and felt authentic, which definitely won my favor.

I also happened to be reading a booked focused on sex at the time, but its cover was more discrete, so I didn’t feel like a weirdo reading it on the train either. It was called The Monogamy Gap: Men, Love, and the Reality of Cheating, and needless to say, it was non-fiction. Alana seemed at least mildly interested, so I went on a monogamy spiel, as I had been doing lately. We talked about how it was hard to separate the mental, physical and emotional parts of a relationship but how it could potentially be helpful.

We were treading on thin ice, talking about this kind of stuff. I knew that, and I tried not to unload all of my criticisms of monogamy, as I knew that I might offend Alana and that it was somewhat hurtful to tell someone I had almost dated for real that I no longer took monogamy seriously. I could feel myself emphasizing my theoretical thoughts over the feeling at the table, which was that we were two people who liked each other, not sociologists.

The conversation morphed to be about marriage, children and all that more adult stuff for a while and we finished our food. Alana was headed to a wedding the next day and, somewhere between the abstract nature of our monogamy discussion and the very real fact that she’d be attending a wedding, I struck a chord and she wanted to change the subject. Her request was fine and I knew it was coming. I don’t know what I was thinking, treading on such thin ice for so long. I should have changed the subject far earlier.

It was time to get going anyway. I knew she wouldn’t want me to, but I pled with Alana to let me pay the bill. She eventually conceded. With all the shit I’d put her through over the previous nine months and that night, it was literally the least I could do.

Also, I finally got up the courage to use a tiny bit of my Italian language education when I asked our water for “il conto.” He was cool about it.

We left the restaurant with plenty of Friday night ahead of us and decided to cap the Italian meal with some gelato. We made our way over to the one time location of L’Arte del Gelato at Barrow Street and 7th Avenue. Picking flavors wasn’t too hard and we decided to share a cioccolato and frutti di bosco cup. We sat on a bench right in front of the shop, ate our gelato and indulged in some people watching. It was a great spot for it. It was a very cute experience, all in all, and I couldn’t remember the last time Alana and I had shared even so much as a moment like that. 

I didn’t do this enough, I told her. I didn’t just sit outside and take in my surroundings. I didn’t press Pause on life and relax for a few minutes without having to worry about being somewhere or entertaining someone. I missed it. I missed Italy in that moment too. It seemed like that was all we did in Italy. Then again, I’d been a summer study abroad student at the time, so the real world was just a fantasy then.

Doing the people watching thing with Alana was super fun. We were both really good at being critical jerks, so it was easy to entertain each other and keep the laughter going as we sat there, well beyond the bottom of our gelato cup.

Eventually though, we decided to walk a little ways to find a bar. We stopped at 55 Bar but didn’t want to pay the cover, so we ended up at The Greenwich Tree House just in time for the end of the FlyersPenguins first round NHL playoff game. Alana couldn’t find her license, only her expired one with a hole in it, but the bouncer let her in anyway. He seemed like a nice guy.

The bar was a bit loud and rowdy at first but calmed down pretty quickly as the game came to a close. We ordered a round of drinks and I went to use the bathroom.

When I returned to Alana and our drinks, she began telling me about something that had happened while she was training for the marathon and I felt compelled to thank her for supporting me when I found out about my dad’s lymphoma diagnosis. For the record, my dad came through it just fine, but Alana had checked in with me every step of the way, always making sure that he and I were both doing all right.

I owed her a sincere thank you and I told her how glad I was that we were out together, that we were going on this date, all the bullshit of our past aside. She said that she was really happy about it too, because she had not been happy with me for a very long time. However, she knew that I was a decent human and that we were able to be there for each other, so she did the tough thing and forgave me, at least enough to salvage a friendship.

Alana even told me that she liked being the Ex-Girlfriend Date. It felt appropriate, she said. She enjoyed feeling special and Ex-Girlfriend Date was certainly reserved for someone special. I knew that when I pitched it to her, I had to be very careful how I framed it and she told me that I had said it perfectly.

Here’s what I had written to her when discussing potential dates:

[Option] 3. Ex-Girlfriend Date: Hear me out. I’m not delusional – I know that we were never boyfriend/girlfriend. But we were definitely “seeing each other” or “dating” or whatever someone would call it. We weren’t merely sleeping together, and I’d never tell the world that. You see, all of my ex-girlfriends have boyfriends and it will be fine if that’s how it is for the next four months, as I expect will be the case. I’m not too worried because it’s a reasonable excuse for not dating one of them. I’ll let myself off the hook if I have to swap this date out. However, our story has a certain weight to it that is at the core of this date. I suppose the point of it, more than the scandal of dating an ex, is to revisit something that had potential. I’m happy, regardless of dating each other, how we’ve put aside our differences and supported one another over the past nine months. You’ve been someone I knew I could count on should some real life shit go down and that’s meant a lot, especially given my own selfishness last summer. The fact that you’ve forgiven me means a great deal and I smiled wide when I saw your email this morning. I don’t want to exploit you, or our relationship, for the sake of this project. That’s not my intention. I’m just walking the fine line of meeting the requirements of my project with the options I have available. I honestly think you’re the best option I have for this date but I’d be happy on any date with you. If you hate this idea, shoot it down and please don’t hate me for suggesting it!

Alana and I looked at each other after she assured me that she was happy to be there and it was a moment to remember. She was so damn endearing sometimes.

She went on to tell me how nervous she had been earlier and that she’d likely been nervous all day. That was probably why she’d had such a stressful day — she was filled with anxiety over this date. I told her that I was happy she powered through. I told her that I had also been nervous at the beginning of our date. I mean, I couldn’t even decide if buying her flowers would have been all right.

On top of all the potential emotional drama and temptation, Alana was also a point of extreme physical desire for me. I admitted to her that in the days and hours leading up to this date, I’d thought a lot about whether or not I’d get to make out with her or sleep with her, but I realized while we sat there that those thoughts had totally faded. I was just so happy to spend time with her. Sleeping with Alana truly hadn’t been on my mind that night, and trust me, it was almost always on my mind. I sincerely just wanted this to be a great date. I wanted her to know that.

Alana and I frequently bonded over music and often, we’d both get hooked on some piece of pop trash. “Call Me Maybe” was the current pop single that we’d reference in inside jokes and conversation, so when it came on at the bar, we had a good laugh. When we first started going out, it was all about Beyoncé’s 4 album, though admittedly, that wasn’t trash.

When I was courting Alana the previous year, I would send her a Jam of the Day (JotD) every day, usually pulling pop and R&B hits from my memory, or occasionally trying to turn her onto something I thought was cool. She had texted me maybe a month before our date that she missed getting them, so I had been sporadically sending her Jams of the Day again. “Call Me Maybe” would have totally been a JotD, but she had heard it before I thought to tell her about it.

Alana’s jam of the day that day was the isolated vocal track from Whitney Houston’s “How Will I Know.” I knew she would like it, but she went so far as to tell me that it gave her chills and told me that she missed Whitney, who had died only two months earlier. At first, I thought she was being dramatic, but then she went into detail about her love of Whitney Houston’s music growing up. Though I knew she had liked her music in a general sense, I had no idea it was so tied to memories of hers and that Whitney’s music was an important part of her childhood soundtrack. I related to her, I said, because I’d had a similar affinity for Michael Jackson, and though people wanted to mock their deaths, there was some actual sense of loss for both of us in the wake of their departures.

Moving on from our sad pop music tales, I told her a couple of the worst stories from my dating adventures. I specifically told her about Moustache Date and Tourist for a Day Date. She cracked a smile and laughed at me variously throughout these stories. She had been wanting and waiting for horror stories this whole time. Obviously, she didn’t just want me to succeed in dating. That wouldn’t have been any fun for her.

We sat in close proximity, but were very comfortable and casual with each other, occasionally bumping our legs together. Nothing too intimate.

After our beers were gone, I asked if she wanted another round as she got up to use to the bathroom. “Only if you do,” she said.

I didn’t. I was tired and I didn’t want to get drunk. And honestly, if there was any chance of us going home together (the thought had since entered my mind), I wanted to to do that sooner rather than later. I thought over the next round while she peed.

Upon her return, we sat at the table for a couple minutes, silently playing the “What’s next?” game, and I finally spoke up. I told her that I was too tired to keep drinking but I wanted to spend more time with her, so if she wanted to go to Queens, or have me to Hoboken, that was what I wanted. My intentions were decent. As I had told her before, I was not trying to sleep with her. I’d stay on the couch for all I cared.

She was game, but I’d have to go to Hoboken. I’d never been more happy to be going to New Jersey.

I paid our tab and used the bathroom. We exited the bar and walked towards the PATH train. The scent of it hit me immediately — I hadn’t taken the PATH in quite some time. It had been even longer since I’d been back to Hoboken, which I hadn’t visited since I had moved out of there 9.5 months earlier.

We boarded a very crowded train car and Alana hardly had an option other than to hold onto me for stability. Her touch was familiar. The closeness we had once shared seemed to return in that moment.

When we exited in Hoboken, I realized that nothing there had changed. The area near the train was such a shit show. I bet people who weren’t familiar with Hoboken would have been surprised by what it could be like on the weekends. It was so different than its quaint facade. Mostly in a bad way.

As we passed a small grocery store, one which I remembered always had flowers outside, I told her to hold up. I wanted to try to pick flowers for her, since I’d second guessed myself twice earlier that day. I chose one variety I thought she might like and she agreed that it was a good choice, but as I went to pick them up, she ordered me to put them down. I tried to explain that I had wanted to get her flowers earlier, and that she wouldn’t have had a choice in the matter. I was just trying to follow through on a thoughtful gesture. 

“You don’t have to,” she said.

“I know! I’m not trying to impress you, but I want to get them for you,” I fired back

“I know, but it’s okay,” she insisted. “It’s the thought that counts,” she said sweetly.

And with that, Alana’s hand dropped down to take mine. I had never been happier to be in New Jersey.

We walked, hand in hand, the 20+ minutes it took to get to her end of town and I recounted memories of living there as we passed by various Hoboken landmarks.

Back at her place, it was apparent fairly quickly that I’d be allowed to stay in her room and that we’d soon be going to bed. She had to locate her driver’s license and get some things together for the wedding the next day, but that was it. To entertain myself, I found her copy of Fifty Shades of Grey and spent a few minutes trying to find a humorous passage.

Sex had reentered my mind since we’d walked hand in hand through the streets of Hoboken and especially after we entered her apartment, but I also knew that I was in a delicate situation and I didn’t want to push any boundaries.

Once Alana had taken care of her things, I lay down next to her on her bed and we had a few minutes of stillness before I kissed her for the first time in nearly 10 months.

We kissed for a little while and at a certain point, she stopped me to say that it was nice, but also weird, to feel like nothing had happened between us, that we’d picked right up again without a bump. Making out with her in her bed, I remembered why I was so attracted to her. All of those physical memories came flooding back and she was right — it had felt like nothing had changed. Finally though, we both needed to sleep, and since I didn’t believe sex going to happen, I was happy to spin down my motors.

While in bed, Alana told me she liked sleeping with me because I actually wanted to touch her. Of course I did. I loved touching her. Who would sleep next to her and not want to touch her? Only a crazy person, I would guess. Also, she said, we were quite complimentary in terms of size — we were a good big spoon and little spoon combination.

There were some shitheads being loud and obnoxious elsewhere in the apartment complex, but they eventually quieted down after Alana and several other neighbors yelled at them. Despite being kept up a bit later than expected, I was in heaven sharing that bed, and my night, with Alana.

She was worth the weight.