High School Friend Date

—Saturday, December 31, 2011—

Wow. I am still somewhat surprised. My 50th date of the project hit at exactly the six month mark. I was incredibly relieved that all the hustle I’d put in had gotten me right where I needed to be. Sure, I may have only been half-way there, but it encouraging to know that I was actually on pace to finish the thing.

Plus, it was New Year’s Eve, a day that’s just one big party. Hell yeah!

In addition to great timing, I also had the perfect date for that night: my friend from high school and beyond, Katie. I may not have pined after Katie when I was a young teenager, the way I had some other girls, but much of that was circumstantial. She had long been in my group of friends, and most commonly, dating one of them when we were younger. Once those walls were put up, they were tough to break down. Add to the situation that I was usually dating someone else in the same group of friends and it is easy to see why we had never crossed romantic paths.

However, we had crossed just about every other path since becoming friends in middle school. We both grew into angst-ridden teenagers who listened to pop-punk, emo and other assorted sub-genres appropriate for suburban adolescents. We both moved between friend groups with relative ease, or rather, maybe we helped evolve our friend groups into one which suited us. We both forged ahead in long-term relationships, even when it seemed like they were doomed.

Most importantly, we had become better friends as time went on. Katie went to school for theatre and I began dabbling in acting while in college, so we related to each other on that level. She was also one of only two or three friends from home to ever visit me over my four years at Fairfield. I remember that trip fondly.

I was stuck at school for the long weekend and Katie had come down to hang out with me. We spent time with friends of mine and everyone got along swimmingly. She shared my bed with me, though nothing at all happened because I was still dating one of our mutual friends. Still, I think that brought us closer than we had been, and though we would drift in and out of intimacy the way any long-distance friends might, I had always maintained a kindred spirit in Katie.

When I asked her out, I was afraid of crossing not a path, but a line. A very long standing friendship line with many other friends potentially watching and waiting for said line to be crossed. I was even more afraid that she might be in a relationship, as I hadn’t checked in with her regarding that topic in quite some time. I didn’t want to offend her or strike out. Both were undesirable.

Fortunately, Katie was single and enthusiastic in accepting my date request. She was even excited to come down to NYC for NYE, which made my life mutherfuckin’ Eazy-E.

High School Friend Date 1

I met Katie in Herald Square, fresh off of her bus ride from Boston. We hugged hello and laughed at how fun and kind of awkward it all was before walking south to Union Square. Before our date night was to begin, we were grabbing beers with our friend Jonno, who was also in town for NYE and happened to be the only other non-girlfriend friend from our hometown who ever visited me at college. I had never shared a bed with him, but I believe we both went to visit Katie (and other friends) at UMASS once, and Jonno had slept on Katie’s floor. Needless to say, we had all been around each other over the years.

We sat with Jonno at Heartland Brewery, had a couple beers and caught up. It was funny for all of us, I think, to know that Katie and I were going on a date later. It was a very different dynamic than anything we’d sat through in our numerous years as friends. Still though, we managed to mostly ignore it and talk about law school in Philadelphia (Jonno), working and acting in Boston (Katie) and all of my bullshit in New York.

Bidding farewell to Jonno, we made promises to keep in touch and visit each other, knowing that we’d probably both get lazy and not follow through. Katie and I departed for Astoria.

Once we were above ground in Queens, I tried to orient Katie to where we were in the grand scheme of New York City, but it probably didn’t mean much to an outsider. Back at my place, she met my roommate Pat for the first time. Additionally, my friend Jack was staying at our place for the evening, which was a friend from yet another walk of life. I loved having different groups of friends hang out. It was a nice way to reassure myself that I was not in some shitty social circle that no one else on Earth would enjoy.

We had some additional time to kill before our dinner reservation and we used it mostly to get changed into our NYE attire. I wore an ill-advised plaid shirt / wool blazer combo and Katie looked cute in her dress/skirt thing. (I clearly needed to pay more attention to women’s clothing.)

High School Friend Date 2

The restaurant was a little bit of a walk and I was nervous that it would be uncomfortably far for Katie, either because of the low temperature or her high heels. She was a trooper though, and assured me that she would be fine. We headed out with plenty of time to get us there for our reservation.

There was a part of me that had been concerned with making dinner plans that night, so I wanted to make sure we were there early. As it turned out, there were not very many parties at Stove that night. It was an Irish-American place, nestled in a Greek neighborhood. We were seated in the back where it was surprisingly somewhat private. I had assumed that the place, that I had never been to nor ever heard anything about, would be packed simply because it was New Year’s Eve. I was happy that such was not the case.

In talking a bit about the project, I told Katie about the next project I wanted to do, assuming I ever had the time. Once again, inspired by Gaby Dunn’s 100 Interviews, I had this idea to do serious interviews with people from my past. Mainly, I wanted to interview many of our mutual friends from high school. For reasons I could only guess, our group had always been oddly private and in particular, we never seemed to discuss relationships or sex. It was like we were all too embarrassed by it, or as I used to feel, protective of our partners’ reputations.

Katie agreed that it was an odd dynamic and we talked about why it might have been the case. Fortunately, it also launched us into a discussion on our past relationships, opening the floor to questions we had perhaps previously felt too embarrassed to ask.

I told her all about my most recent girlfriend, She Who Shall Not Be Named, and she related the saga of her freshest ex-boyfriend, who I had spent some time around while in Boston. I knew that it had been a significant relationship for her and I assumed the breakup was bad, but I didn’t really know how bad. They were still dating when I moved to New York, so it was all assumptions on my part. From the sounds of it, it had been a tough one. Not that any breakups are easy, but some really hit you like a train with no intention of slowing down.

The meal was delicious and we topped it all off with blueberry pie. I really like pie.

It was not until I got a couple text messages from expectant friends, that I realized we had taken our sweet ass time with dinner. We paid for our meal and breezed out the door toward my friends Dan and Oz’s apartment, a short walk away.

As we made our way to the party, we continued to reminisce about high school friend dynamics. I made a crack about how all the girls must have wanted our friend who was a singer and it made Katie laugh. I mean, he had fronted both bands which made up our core group of friends.

I don’t know if everyone has played this game, but in high school, my girlfriend and I would discuss our “If you had to choose one of our friends to cheat with…” choices and I told Katie that singer boy had been my girlfriend’s pick. I realize now that it was actually one of the guitarists, but it doesn’t really matter.

Picking up on what I was putting down, Katie asked who my “cheat” was at that time. “Well, actually,” I hesitated, “you were.”

She laughed a good laugh, and she maybe even blushed, but it was too dark out to tell. What came next was nothing short of adorable.

“You were mine too,” Katie said with a smile.

Well, check that out! We had both been curious about each other in high school and there we were, all grown up, going to a New Year’s Eve party together. It was an honest to goodness date.

It was funny, finding that out after so many years. We attempted to calculate how long we’d known each other and decided that it had been about 13 years. One-three. 13! That was half of my life. Whoa.

Katie had been worried that my friends at the party would think she was some random OkCupid girl that I had convinced to tag along for the night, but I assured her that wouldn’t be the case. Plus, she had met my pal Tony before and he would be there to vouch for her existence.

We finally arrived at the party around 10:30 p.m. and upon entering Dan and Oz’s apartment, some people yelled “Hey, Evan!” and I waved back all like, “Hey everyone. This is Katie.”

“Hi, Katie!”

“Hey, everyone!”

I grabbed us some drinks and we talked with roommate Pat and his then girlfriend Lindsey. It was a solid match up — two roommates and their dates who didn’t really know anyone else there.

Soon enough, we started bouncing around, saying hello to people and introducing Katie. My friends were all so damn friendly that it was soon easy to leave Katie on her own. She was super friendly and they were all very funny, so I really didn’t need to worry or babysit her. My very good friend Ioanna talked to Katie at length, and though I had no idea what they were saying, I was happy to see two of my best friends, one from high school and one from college, laughing with each other and getting along.

In what seemed like only minutes, everyone was discussing the approaching ball drop. Wow. That had flown by, but sure enough, we were counting down to 2012.

10, 9, 8, 7, 6, 5, 4, 3, 2, 1….Happy New Year!

Katie and I looked at each other, half-giggled, shrugged “what the hell?” and kissed each other.

The following hour consisted of some light dancing, light drinking and most of the party shuffling out. Jack, who was sleeping in my living room that night, had left soon after midnight.

By the time 1 a.m. rolled around, it was Pat, Lindsey, Ioanna, Austin (her boo), Katie and I. We all thanked our hosts and walked back towards our respective apartments. About five minutes from home, Austin and Ioanna peeled off towards her place and the four of us continued on. I don’t know when all of our college friends had gotten so old and lame, but I suppose I appreciated it that night. It was nice to get back home and not be staggeringly drunk nor comatose tired.

Back at my place, we all tiptoed around Jack in our living room and the couples split to their respective rooms.

Katie and I stayed up for a long time talking about all sorts of things — Astoria, Greek people, the movie ‘Soul Surfer’, travel, Xanga…until I eventually revisited what we’d touched on earlier. I kissed her. I kissed her a bunch.

—Sunday, January 1, 2012—

Though we hadn’t made a conscious choice to do so, Katie and I slept in very late and stayed in bed until 2 or 3 p.m. For the first time I that I could remember, Katie and I discussed family matters at length. There were a lot of things in my life that I had never shared with most of my high school friends and it was a relief to unload on Katie. I knew that I could count on her to be understanding and sympathetic. She had a good heart.

It was an incredibly interesting experience, spending the night with a very old friend, with no walls up or peers watching over you. It was remarkable, in a way, that it had only happened once in 13 years of friendship, but then again, that was most friendships I had with women. The territory was certainly new, but that didn’t mean it was uncomfortable or even “weird”, whatever that means.

Being January 1st and all, I used the spare moments I had to myself to reflect on my 2011. A year earlier, I had spoken to She Who Shall Not Be Named for the last time (so I thought). It had been a depressing day spent cleaning, doing laundry and making chili until my friends Tony and Sarah picked me up to hang out. Also, I had eaten a pot brownie that day and was high for the first time in my life. After eating some sushi, I fell asleep on a futon, hugging their dog while Harry Potter & The Half-Blood Prince played. It was a fitting day for how all over the map 2011 turned out to be.

My first tryst of 2011 was the former girlfriend of my then roommate for a single night. I swear I didn’t know that was the situation, but I found myself in potentially hot water almost as soon as I had been released to the single world. Then I went on my first date, with someone from the improv community, no less. She became the first woman I ever “dated’. I had a one night stand with a woman from OkCupid. I reconnected with an old college friend whom I was never very close to. I met a woman with Aquanet hair at my local Hoboken bar. Then, I fell for a woman I’d admired from afar in college until I broke things off to start this whole ridiculous experiment. 2011 was a year packed full of new experiences with women.

In fact, I’d had so many different relationships with women over the previous year that the experience with Katie wasn’t just “not weird”, it was actually calming and highly enjoyable.

Instead of meeting someone new and trying to pack in all the getting-to-know-them that I could, I was in the midst of two full days spent with an old friend, discovering new things that had always been just below the surface — things only out of reach because I had never asked. These were some of the easiest, and yet most satisfying, moments of this project thus far.

Without a doubt, I will be judged for saying that I would like to have similar experiences with more of my friends. As someone who never wants to be classified as sex-obsessed, and as someone who genuinely values friendships with women, I have always feared admitting that it would be cool to hook up with my friends. I hope people know that it comes from a place of respect, love and genuine curiosity. It’s as much about kissing as it is about their stories and their willingness to maybe burp in my presence. With intimacy often comes a tendency to let walls down. And plus, you spend so much time with certain people that you have all the conversations in the world, but hooking up is one conversation I haven’t had with most and it seems worthy of a discussion.

By the time we left for my local diner to have “breakfast”, it was nearly dusk. The meal was spent talking mostly about theater, improv, comedy and particularly, the immersive theatrical experience that is Sleep No More. Katie said she wanted to come back down and see it within the next couple months and I offered to go with her. I loved that show. I could stand to see it a third time.

It was dark by the time we walked back through the park to my apartment and the shitty thing was, I was fucking tired. I wanted to show Katie a good time while she was there in New York, but I didn’t feel like doing a damn thing. Plus, it was New Year’s Day and little would be open. Luckily, Katie felt similarly tired. Must have been some kind of sleep hangover. We agreed to just lounge about and watch movies.

Hours melted away as we watched Spider-Man and Spider-Man 2 from my bed. We probably would have watched the third one too, but luckily, I didn’t own that steaming heap of a movie. It was for the best since we actually got out of bed and reentered the human world.

Keeping it in the neighborhood, or avenue, to be specific, we walked down to Sparrow Tavern for drinks. We spent a beer or two talking about Italy, Spain and the variety of bars all over the world. She was taking off for London in a week, which would be chock full of good pub times. I told her about Angie’s in Florence — one of my favorite bars in the world. It was owned by three friends who all tended the bar, talked with customers and spun music, and the resulting vibe was unbeatable.

Both Katie and I had aspirations of living all over the stupid world, and though such things seemed impossible at the moment, they sure were nice to fantasize about.

Between our passions for entertaining others and traveling the globe, Katie and I likely had more big things in common with each other than any of our other friends from home. And in just a few months, Katie would jump on the “move to a big city” train and become our first friend in sunny Los Angeles, solidifying another connection between us, though adding some considerable physical distance.

After finishing up at Sparrow, it only made sense to wander even closer to home and so we stopped into Mosaic, which was right next door to where I lived. It was late, but we asked if they had any food for us to snack on. As luck would have it, they still had leftover chicken wings from their NYE party the previous night and they were giving them away for free. We had a couple beers and went for seconds on the wings, which despite being fairly cold, were quite tasty.

We talked late into the night and left as it approached 4 a.m., thanking the staff for their hospitality. Good thing we had slept in that day.

—Monday, January 2, 2012—

Having woken up and showered, Katie and I went to the deli down the street for breakfast. While I ordered a bacon, egg and cheese sandwich, Katie opted for a ham, egg and cheese sandwich — a slap in the face to the bacon-frenzied movement of the previous two years. (In subsequent weeks, I would try the ham substitution and ended up loving it. I order it regularly now.) We ate and chatted and tried to shake off the morning rust.

Her bus back to Boston was leaving Chinatown that afternoon, so we decided to go into the area and wander around. After walking through Little Italy, which was quite little, we ended up at the Tenement Museum. Though we didn’t have time for a full tour, we were able to sit in on an introductory film about the history of tenements in New York and the establishment of the museum. It was very interesting. I should go back for the tour.

Walking back down to Chinatown, Katie and I talked about our respective heritages and first-generation friends. The tenement museum particularly resonated with her Irish blood, though she herself was a couple generations removed.

I waited in line with Katie until she was able to get on a bus to Beantown. I bade her a fond farewell, knowing that I would cherish this isolated weekend in which we both took a break from reality and got to know each other better than ever before. I hoped to do it again sometime.