Cocktail Date

—Friday, October 21, 2011—

It had been almost eight months since I’d been in Boston, since I’d been back in my home city, and it had been even longer since I’d been in love. Sometimes you just know when you’ve been away too long.

I was two beers deep and feeling sleep deprived after taking a 1:30 a.m. bus from New York City that morning. My afternoon had been spent groggily hanging out with some friends at a bar — the bar where Julie worked. She was my Comic Con Date from the week before. I met my friends there after Julie and I ate lunch together and she had punched in. Twice in seven days, I’d seen her, and damn, I liked her. I wanted her. I wanted to love her.

But it was still so new. We had no idea how it would play out.

In the meantime, I had a date with Katherine and a whole bunch of cocktails.

Cocktail Date 1

To combat my lethargy, I sucked down a double espresso on my walk to Green Street, in Central Square, Cambridge. It seemed to do the trick and I perked up as I approached the restaurant.

Since we were t0 be drinking a fair number of libations that night, we needed a proper meal at the onset and Green Street was a fantastic place to start. It was one of the places I never made it to while living in Boston but I had always heard fabulous things about both its drinks and cuisine. In fact, all three establishments on the Red Line mini tour de booze I had planned for that were missed connections I’d had with the Boston foodie scene.

Throughout the project thus far, I’d had to be rather opportunistic when it came to landing dates, and my date with Katherine was no exception. She had found out about OHD from a mutual Fairfield friend and then sent me a message on Facebook to tell me she was enjoying the posts. After speaking with our friend Kosta, he assured me that Katherine was then single and that I should ask her out. She seemed very nice and rather cute, so I was glad to have the green light.

He also posited that she would sleep with me on the first date, and while I took his statement with a grain of salt, the prospect was still enticing to think about. I asked Katherine if she’d like to go on a date the next time I was in Boston and so we found ourselves meeting up at Green Street.

Katherine arrived with laughter and smiles. As Kosta had described her, and fitting what I’d seen on Facebook, she was very cute. My fingers were immediately crossed for the whole potential sex thing.

It was actually surprising that we had never met, considering that we knew so many people in common. While acquainting ourselves, it seemed like some of the people I knew the best in her grade were some of her closest friends. We reminisced about all things Fairfield: the Jogues Hall shit show that was her freshman year, the meaningful “living and learning” community from her Sophomore year and of course, the notorious Fairfield beach scene.

Kosta himself became a topic of much conversation between the two of us. Despite his sometimes crude mind, he was one of the most genuine guys I knew from college. The main reason why Kosta and I had ever been friends was because we both had a duality about us and we related to each other on that level. Kosta was a nice guy trapped in the shell of a bro; and as Katherine told me, I was essentially the reverse.

Wait. Excuse me? I was a bro trapped in the shell of a nice guy? Uh oh.

She told me that Kosta had described me as a “Bro in disguise,” claiming that my indie rock facade was just that, a cover. Yowzers — that was unexpected. I had never been described in that way. However, considering it was the second woman I’d gone out with that day, and I was hoping to sleep with her, maybe there was some merit to her claim.

The important thing was that Katherine didn’t hold it against me, because much like Kosta and I, she tended to be a social chameleon herself. She liked to party as much as she liked to relax and do nothing.

All in all, it took us a while to order drinks and then food because we were talking so much. I ordered a Bohemian, which was gin, St. Germain, grapefruit juice and bitters. I was not well experienced with mixed drinks, so as much as I felt compelled to branch out from my usual gin & tonic / mojito habit, I was not ready to stray too far. Katherine ordered a modern margarita, which sounded lovely on the menu. For food, she selected the pan roasted gianonne chicken and I got the lobster and mushroom ravioletti. We also ordered a duck confit and gnocchi appetizer. It was shaping up to be a splendid meal.

Cocktail Date 2

Katherine told me about growing up as a first generation Portuguese-American in Massachusetts, with a large family in the area. Similar to my father, both of Katherine’s parents had worked their way up from humble beginnings to lead more prosperous lives.

Much of what we discussed related to my other friends from Fairfield, in particular, Tony, Austin and Ioanna — all first generation Americans whose parents worked very hard for everything they had. Although my father wasn’t an immigrant to this country, he had experienced a similar journey, starting life as a poor farmer’s son in Vermont and later living in an affluent suburb outside of Boston. I have often told people that my dad lived two generations in one lifetime. He went from a one room country school house to putting two children through college. I had always been proud of that. I could only assume it was that much more inspiring for Katherine to know that her parents had come all the way from another country to achieve such heights.

The food was delicious. It was simple in design but rich and wonderful in flavor. I was very happy with the dinner.

The restaurant filled up during the course of our meal and Green Street went from hushed to bustling. Katherine told me about where she lived in Southie and I compared it to Hoboken, NJ by saying that it was filled with a bunch of people in their 20‘s and 30‘s who wanted to keep doing what they had done in college. This did not only apply to drunken adventures, but also to relationships. The idea of hooking up and remaining unchained prevailed in such communities.

We talked about OHD a bit and Katherine said that she wouldn’t be able to do a project like it. She couldn’t imagine finding all the dates and said that men still didn’t ask women out very often, especially not in douchbag-laden areas like Faneuil Hall. She told of a man who once approached her and asked “What are you, Indian?” as his pickup line. I’d heard of some stupid ways to start a conversation with a woman, but assuming her race and presenting it in such a careless way was, pardon my French, dumb as fuck.

As we exited Green Street and walked to the T, we discussed chivalry, paying for dates and how on Earth I could afford this project. My saving grace was that I have lived at home for almost two years after graduating college and I had savings from that time. OHD was my own small business venture, in a way, though two and a half years later, I still haven’t made a single dollar from it. Fuck me, right?

Katherine and I rose from the Park Street station and walked up Beacon Hill to our second stop, the Barbara Lynch institution, No. 9 Park. Growing up, this was the place that I knew as “that really fancy spot by the “State House” and indeed, it was amongst the swankiest restaurants in Boston. It was the sort of place that might see people our age, dressed as we were, and turn their noses up or simply turn us away. Fortunately, we had no problems whatsoever. In fact, the service was top notch. I must have been imagining that air of superiority.

We talked about Barbara Lynch and her recent mission to turn around the Fort Point neighborhood by opening her trio of new establishments over the previous few years. Katherine had actually been brought on a date to one of Lynch’s restaurants, Sportello, and I laughed as she told me this because it was such an amateur move. Sportello was a high-end lunch place, and all counter service, which did not make for a romantic evening. You cannot bring a date to an expensive lunch spot on a first date simply because you think the attachment to Barbara Lynch will impress your company. It’s foolish to think they won’t see it for what it is and it’s simply not the right attitude to have.

For drinks, we ordered a pair of interesting concoctions, the names of which I immediately forgot. To be honest, I didn’t love mine, but it wasn’t bad either. It tasted kind of like a pine tree. I didn’t even ask if Katherine liked hers because we were too wrapped up in conversation. We talked about relationships past and swapped crazy drunken night stories, focusing on those that we’d had overseas. Mistakes without borders.

Traveling was definitely something both Katherine and would have liked to do more often. I brought up my friend Tony again, as we had traveled to Guatemala together in 2010, and I realized I had mentioned him numerous times already that night. I think it was because he was first generation Portuguese and there was a lot that he and Katherine had in common, but also because Tony and I had much in common as well. It was the perfect storm to make it sound like Tony was my only friend. I made a note to mention someone else the next time I needed an anecdote.

Our second round of cocktails entailed something called a No. 10 and a Pisco Punch. These were really great and a marked improvement on our first round. They went down more quickly and soon enough it was time to get a move on to our third cocktail bar. I had to keep in mind that Boston closed by 2 a.m.

Cocktail Date 3

Leaving No. 9 Park, we caught the Red Line to Southie, only a few stops away, and Franklin Café Southie was just a couple blocks south of the T stop on Dorcester Avenue. This was the second outpost of the popular South End eatery and while it was definitely a bit “Southier” than the original, it still had a better than average cocktail menu.

The only two seats at the bar looked to be guarded by a group of frat brothers who had no idea why they were at a non-Irish bar. Despite their thoughtless appearance and Bud Light Limes, they were kind enough to offer us the seats.

After a minute or two of deliberation, I ordered a cucumber Collins and Katherine got an Anejo lemonade. They were both refreshing and seemed like a decently calm way to end the evening. If only our evening had truly been winding down.

It was clear by this time that we were starting to get tired and that the drinks in hand would likely be our last round. Of course, within 10 minutes of sitting down, the scene around us picked up. It was the bartender’s birthday and a group of people entered with balloons, making it louder and louder. Eventually, a large, outspoken Texan said hello to us and distracted from our enthralling conversation about whatever was less exciting than the number of beers he was about to order.

I checked my phone on my way to the bathroom and saw that it was 1:30 a.m. Damn, I hand’t though it was that late. Getting back to my brother’s place in Medford was not going to be cheap. I originally hadn’t been worried about ending the night in Southie because of Kosta’s guarantee of a sleepover, but since I hadn’t been getting that vibe from Katherine, I was no longer expecting anything to that extent. At that time, I was worried about looking dumb for being so far away from home.

Cocktail Date 4

Returning from the bathroom, I saw the large Texan talking to Katherine. He told me that I was very lucky to be there with such a beautiful woman. While I couldn’t help but agree with him, he was also blatantly hitting on Katherine by saying these things to me. Thanks man, that’s great. I’m glad I commanded such little respect that he felt he could flirt with my date right in front of me. If I had had an extra 160 pounds on me, I might have actually said something to him.

Tex asked where we both lived and since I was so far away, he strongly suggested to Katherine that she should let me stay at her place. In the way he said it, he was practically insisting that she have sex with me. You know, maybe I should have thanked that guy. Compared to him, I was awesome. I was the most well behaved gentleman in the world compared to that gregarious buffoon.

He then asked if he could buy us drinks, as if that was going to help him win our favor back. We obliged, because we figured we might as well get something good from the encounter, and he bought Katherine a vodka soda and me a gin and tonic. Katherine thought the whole thing was extremely rude and disrespectful, and while I shrugged it off in the moment, it did irk me a decent amount.

We decided to leave after a few sips of our drinks and following the rendition of Happy Birthday sung to the bartender.  She had mentioned after the Texan conversation that if I did in fact need a place to stay, her couch was open. I asked her if the offer still stood and she said of course. We had a good rapport and I was relieved that Katherine trusted me. I knew I trusted her. I don’t know why I wouldn’t have trusted her, but the mutual feeling seemed to me what mattered.

A taxi brought us to her place maybe a five or ten minute ride away. Katherine showed me around her apartment, which was very nice, and then got some blankets and a pillow for me. She placed the lot of them on the couch and as I went to hug her goodnight, I kissed her.

We paused and she laughed, which is what most women do when they find themselves kissing me. “We’re making out in my living room,” she said. Well, the bedroom was decidedly a better option, but that hadn’t been offered. We kissed again and then she went to bed, wishing me a goodnight.

I looked at the couch and I wondered what Katherine really wanted from me. I thought about what Kosta had been telling me and I wondered. I though to myself, “Kosta knows her well. Should I trust him, or trust what I’ve seen tonight? Maybe she’s just being shy.” I used the bathroom and then I knocked on her door.

“I know we just met and I don’t want to be a Drunk Kosta*, but I’d be much happier sleeping in your bed,” were the oh so clever words that I uttered when she opened the door.

She laughed and said that of course I could sleep in her bed, she just didn’t know if it was against the rules of OHD. I climbed into her tall bed and the desire to sleep hit me immediately. I was so damn tired and generally worn down. I remembered that I took a 1:30 a.m. bus from NYC the night before and I could feel my body giving up.

Katherine eventually climbed into bed herself and we amused ourselves by commenting on whichever HGTV show it was that we were watching. Hammer Heads? Kitchen Cousins? I don’t know. I finally got her attention in a face-to-face kind of way and I kissed her again. We made out for a bit but it didn’t go anywhere graphic, so you can all calm down.

I fell asleep with my arms around her and ours legs intertwined, kind of how most women sleep on a man’s chest. It was completely emasculating and I realized how much I missed that feeling of giving over to another person.

Sex was just one thing that came with a girlfriend, but I missed moments like this even more, where I could hold someone and let my guard down. I woke briefly after what I hoped was only a few minutes and I realized that Katherine was likely a bit uncomfortable. I rolled off of her and she turned to her side immediately. I didn’t blame her. A few minutes later, I rolled over and passed out.

Katherine woke me up the next day and we spent an hour and half on her couch, under blankets, watching reality television. It was nice to just zone out and enjoy some downtime with a woman. It didn’t happen often enough those days.

I was grateful for Katherine because in the final stages of this date, she flipped my expectations and made me realize that they had been foolish to begin with. I had come into this date thinking I had a good chance of having sex, and while that would have been awesome, I was much happier just to have that bed to sleep in and her to hold.

Katherine had shown me trust and I know that trying to force any other agenda wouldn’t have felt right. Sex wasn’t a part of the plan and instead, I was reminded of the things I missed the most.

Sometimes you just know when you’ve been away too long.

*Kosta, our mutual friend, had a penchant at school for crawling into his friends’ beds when drunk and Platonically sleeping next to them. He was a giant man and this was often humorous.