Secret Date

—Friday, July 22, 2011—

Operation: SECRET DATE


Objective 1: Secure actual date with target

Objective 2: Carry out date in secrecy

Objective 3: Inform target of secret date

Objective 4: Escape with life

The target was contacted exactly nine days earlier. I was looking to see if Leigh would be in town that coming weekend. She had told me it would “probably be fine” and so I blocked out the time on my calendar. I waited, sans contact, for over a week. It was important not to come off as overly eager or needy. Otherwise, she might have been suspicious. I texted her again the day before the date and began planning the evening. It needed to be simple, low key even. Nothing that would draw attention. I used phrases like “grab food”, “do drinks”, and “whatever.” I told her that I had to be at call for my show by 9:30 p.m. It was meant to be quick and fun.

The utmost effort had been made to ensure that Leigh had no idea she’d been asked on a date.

My co-workers were not convinced. They thought she would assume I’d asked her on a date. I informed them that it wasn’t like that between Leigh and I. I explained how I knew Leigh and why she had no reason to believe I was asking her on a date.

Leigh had moved to Hoboken, NJ at the beginning of June 2011, just one month before I moved out of that God forsaken town (j/k – It’s really pretty nice). On the 2nd of the month, she sent me a message on CouchSurfing, explaining how she was new to CS and new to Hoboken, where she was on her own since leaving all of her best friends up in Boston. Leigh was using CS to find other folks in Hoboken and wanted to know if I would be free to get a drink and tell her about the city. I met her that night to watch the end of an NBA Finals game.

I had seen some pictures of her on her CS profile, but they didn’t do her justice. She was better dressed than I expected and even had on heels, though we met up a a local dive bar. Her hair was straight and fell perfectly around her face. Wham, bam, thank you ma’am. She looked like a million bucks that night.

Leigh had been there at the bar alone for some time, entertaining an old drunk, when I arrived. Clearly, she had a confidence that defied many people arriving in a new city. As we talked that night, I learned that she was a high school history teacher in a prosperous suburb nearby; that she liked sports; that she appreciated dive bars; and that she was adventurous. Something about her had already tipped me off to that last detail. CouchSurfers tended to be an adventurous bunch.

When I walked into work the next day and told my co-workers of my meeting with Leigh, they told me that she sounded like something out of a movie. I can only imagine a young damsel hastily entering a private eye office: “Oh, I’m sorry to bother you mister, but I just moved here and I’m oh so lonesome. Might I be able to buy you a beer at one of your favorite establishments while we discuss things you’re interested in? I promise to dress up and look pretty.” She just seemed to good to be true.

Only two days later, Leigh and I rendezvoused in Manhattan after one of my improv shows. She briefly met a number of my friends, but for the most part, she and I spoke privately for over two hours. Once again, she could have stopped traffic, the way she looked. On that second night, our conversation did more than just scratch the surface. We touched on some things that connected us. Some real shit, as they say on the streets (in movies). The best part of the evening though, was grabbing late-night falafel together back in Hoboken. It was at that point that I knew she was my kind of human. Shockingly however, there didn’t seem to be any spark between us. Her interest in me seemed to be very much Platonic, and so I played it cool. My flirting was kept to an absolute minimum.

The absence of sparks between us, and my lack of flirting, didn’t mean I wasn’t interested — I simply knew better.

Leigh had reached out to me in an earnest attempt to connect and get to know a new place. She trusted me to be the kind ambassador to Hoboken that my CS profile, and general behavior, had made me out to be. Not to mention, I was starting the project very soon and didn’t want to get involved with her as I attempted to begin a year of being single.

Additionally, I had already taken up with Alana, a woman I accidentally started dating right before OHD began, and was in the midst of dealing with the sad experience of breaking things off with her in order to date other women for a year. More on her later in the interet.

So, in the grand scheme of things, dating Leigh just wasn’t an option at that time.

Since that night with the falafel, we had been in touch sporadically, checking in with each other every couple weeks to see if the other was around town. Things simply didn’t sync up for some time. Until the night of our secret OHD date, that is.

Given our rapport, it wasn’t out of the blue or even the least bit odd that I was asking to get together. We were still in that friendship forming phase of the relationship and we had no mutual friends or activities to connect us. The only way to see each other was to make a concerted effort.

One of my co-workers had commented that a Secret Date was the antithesis of One Hundred Dates. If anything, it was among the old, non-confrontational means of securing a date that I’d probably used in the past. Indeed, I had often been indirect with women my entire life. I understood his logic and so I made it a goal for myself to incorporate the greater themes of OHD into the date that night. Specifically, honesty and risk taking.

By the end of the date, Leigh would have to know about the project.

I arrived at the restaurant, Mappamondo, roughly ten minutes early and sat in the sweltering sun. It was a scorcher that day. It was so hot out, I could have fried an egg on the sidewalk. It was a dog day afternoon and I wasn’t no dog, baby. I was sweating through every piece of clothing I had on, but I knew it would be forgiven. After all, it was one of those days where everyone was sweating like a pug in a Christmas sweater.

Leigh arrived on time and I greeted her with a hug, asking her how she was. “Sweaty,” she told me, as if I had clearly figured that out from our embrace.

I thought the same thing then as I did when I first met her, and the second time for that matter: she was so pretty. I won’t try to paint a picture here, but if I were to, it would be mostly water colors. (I was never very good with oils or acrylics. I should have taken a couple more art classes.) Anyway, looks were not even the main reason I was interested in Leigh. There were a lot of pretty faces out there. She excited me because she was actually someone I enjoyed hanging out with, and I didn’t even have to be flirting with her! Most women who have met me even a couple times are usually subjected to some flavor of the sad ice cream sundae that is my game.

We were greeted by the manager and, even though the restaurant was only a third full, he asked immediately if we had a reservation. I assured him that we did. It was a small, casual Italian place and we slid into our bench seats near the front left window. As we settled in, we checked out the menus.

It was too hot for booze. That much was figured out quickly. We were checked on at least twice before we were ready to order.  Appetizers of a shrimp and white bean dish as well as bruschetta laid the way for our dueling main-course salads. I certainly didn’t feel like dealing with anything heavy on a night with such oppressive heat. Good thing I left my mommy issues at the door.

Leigh caught me up on what she’d been doing over the previous month or so. I recognized much of it from the text messages we’d exchanged, but it was good to hear about those things in detail. Away to Chicago for a teacher’s conference, away with her family in Vermont, celebrating her birthday in town with a good friend. All things I was happy to be caught up on. I told her a bit with my past month, but didn’t go into great detail. After all, it was pretty much all improv and OHD, and how interesting could either of those have been?

Mere minutes passed before our appetizers arrived. We made regular length work of them.

The most recent Harry Potter movie was brought up, with both of us geeking out a bit over the film. She went to a midnight showing with her sister. I asked her if she had dressed up and, though she hadn’t for that one, she told that she had in the past. She said her students didn’t know how to react to their teacher dressed up for a movie premiere in school. Teenagers, huh? They wouldn’t know a good idea if it unhooked its bra and started talking about new experiences.

I was reminded during her anecdote that Leigh was the hot young teacher at her school. I’d explicitly asked her about that topic before. In a profession with so many older adults and academic types, I couldn’t imagine being in that role without being aware of it. She reminded me a lot of Ms. Keane, my Spanish teacher from freshman year of high school. There were only a few young teachers at our school, so it didn’t take too much for Ms. Keane to be deemed ‘hot’. I never expected to be on a date, however secret, with a hot teacher. LOOK AT ME NOW, MOM!

She laughed quite a bit as we talked and she frequently moved her hair from one side on her neck to the other on account of the heat. It was adorable. I told her that the only movie I’d ever dressed up for prior to HP7.2 was Batman Begins. My friend Kevin was Batman and I was Robin. That led us to recount our past Halloween costumes and I admitted that I actually wore the Robin costume three years in a row. In fact, I think I still had it laying around somewhere at that time.

It was easy talking with Leigh and our conversation continued uninterrupted as our salads arrived at the table. She told me about how she was working on challenging herself to get out of her shell and do more things she might not normally do, and so I told her about how I was doing the same thing. I told her about OHD and I was shaking as the words left my mouth. My hand nearly dropped the fork it held while I waited for her to ask me if we were on a date. Minutes passed and she offered no inquiry.

Instead, my gamble opened a door. Leigh told me that she had the same history with relationships as I did. She had also been in three long-term relationships over roughly ten years. The durations of our relationships were even similar. “I hardly ever do anything important,” I told her, “unless I force myself to, and so this is my way of pushing that.” She thought the whole OHD idea was cool and definitely a good goal for me to have.

Leigh was goal oriented. She related to me how she grew up having goals and how realizing them had been her way of measuring success. Her goals were also her way of staying busy. Since she was no longer in school and working in a job that she loved, she seemed to have run out of short term goals. Sure, there were big ones on their way, such as owning a home and getting married, but those were far off at the time. In the meantime, it was not so clear to her what she should be doing.

I’d been living with that feeling my entire life. I never had concrete goals. Being busy was my way of finding goals, but it seemed that there were always more to discover. She noted that it could be confusing at times to separate goals from desires. For example, although she didn’t necessarily want a PhD, she was tempted to pursue one simply because it was the next logical step.

The staff asked us if we would like dessert and we split a small chocolate torte à la mode. It was surprisingly decent — I wasn’t expecting much.

Not to blow it out of proportion, but the dessert was a really nice moment to share with Leigh. I don’t know that I’d ever shared a dessert with a friend, especially not something with chocolate, strawberries and ice cream, but for a few minutes, I didn’t feel like the date was a secret. I am sure nothing had changed noticeably, but I felt more at ease and less like I was hiding something. Still, it was no time to spill the beans.

We split the check, as friends would do, and I didn’t even offer to pay. That would have aroused suspicion for sure. We left the small restaurant and headed out into the heat, like a pair of people going out into a really hot environment, and found the White Horse Tavern soon enough. I ordered a cider. It had been a while since I’d had one. Leigh ordered a beer, keeping our masculine/feminine energies in check. We had been discussing comic books and by the time our drinks arrived, comic book movies.

I love talking about comic books with women. There was a period of my teens where I ignored comics, as if they hadn’t consumed my childhood. I didn’t think they were cool anymore. Even now, after years of getting back into them, I am very anxious about women finding my stash. Talking to a woman who not only thinks it’s okay for me to like superheroes, but also engages in the conversation with me, is refreshing. I wager my friend Kevin (Batman) would have been jealous.

It took me some time, but I finally asked Leigh about the two tattoos on her arms. I asked because I was on the verge of getting my first. The one on her left wrist was in either Latin or Greek, I believe, and it translated to, “Know Thyself.” She related how she liked to explore self reflection quite a bit so when she stumbled upon the phrase one day, she connected with it immediately. Her second tattoo was a small anchor on her right forearm which was for her grandfather and great-grandfather who had both been in the Navy. She said she wanted more tattoos though, specifically a flower on her left forearm. She described it to me and it sounded beautiful.

Leigh asked about the tattoo I wanted and I told her of a design which would serve as a memorial to loved ones lost. She was prompted to tell me that she had also been wanting Mexican skulls on her right arm, like you’d see during Día de Los Muertos. She liked the idea of celebrating life after a death rather than simply mourning.

I was right on the same page. We’d both lost our mothers. It was something we connected over the second time we hung out. It’s a particular bond that I get to share with the occasional person in my life, and while it’s not going to make me love someone I hate, it invariably creates a level of understanding between the two of us. It’s good talking to someone who truly knows the feeling of losing a mother, even when you’re not actively discussing it. It just has a way of bleeding into everything, as mothers are wont to do.

It was nearly time for me to leave for my show as we finished our drinks. The server brought us the check and as we waited on payment to process, I smiled to myself the way I do when I’m embarrassed. I remembered the promise I made to myself before I left work. I gathered my courage and asked Leigh if she would like to go out on a date sometime. I admitted to her that I’d wanted to ask her out since meeting her but hadn’t had the guts to do so before starting the project.

To my delight, she accepted the offer. I felt the way a daredevil must feel when he hits that airbag after being shot out of a cannon, except I mean it in an emotional way whereas I imagine a daredevil feels that softened landing in a more literal, physical sense.

I then got even more nervous and more smiley as I told her that she had been on one of the hundred dates the entire time. She was surprised, but not angry with me. I asked if she had any idea that we were on a date. She didn’t have a clue, she said. She then asked me which date we were one and so I revealed to her that she’d been on a Secret Date. Leigh was a good sport. She was actually okay with the whole thing. It was about as successful as a secret date could have been.

We left the bar and said farewell before parting ways. I apologized for tricking her and she told me it was nothing to worry about. She actually looked happy to have been out with me and maybe even a little excited to go on an actual date. I hoped she was, because I was counting down the days like a schoolboy waiting for summer.

Mission Status: COMPLETE

Mission Update: Well, like most things that seem too good to be true, Leigh turned out to be more elusive that I had originally thought. I waited too long to ask her out on that second date and by the time I reached out to her in October (three months later) about it, she had started seeing someone new. From reading her lovely blog, I pieced together the story. They met roughly a month after our date, fell madly in love and now, two and half years later, are engaged to be married. Damn — I really missed the boat on that one. But you know, I guess it’s better that they found each other. After all, I’m still drifting in the world of single.