Bartender Date

—Saturday, June 16, 2012 —

One myth I wasn’t able to truly able to debunk during OHD? That female bartenders were the most impossible dates to get. I found a way to make it happen, of course, but it wasn’t easy.

A week before this date, I had come home after a long Friday at work and was totally beat. I’d had a very full week, with a few late nights, and I wasn’t going to go out that evening. That was, before I saw a ray of hope.

Staring at my phone, on my bed and moments away from passing out, I saw a post from Kerry on my newsfeed that read: “Guys. GUYS! I’m wearing suspenders behind the bar. Come check it out.” I sat up with a flash of energy upon realizing that one of my loose Facebook friends was a bartender.

I commented on her post with, “Unfair. I have no idea where you work. :-/”

Two minutes later, Kerry replied with the name of the bar and its location.

It looked like I was going out that night after all. And soon.

I quickly scanned my brain for single friends who might be able to wing me at an Upper East Side bar last minute on a Friday night and then shot a text message to my co-worker Varun, who lived in the area. As luck would have it, he was available and we made a plan to meet up at 10 p.m. Fortunately, my closest co-workers, of which Varun was one, were well aware of my struggle to find a bartender date.

I’d been going out a lot recently with the intention of asking a bartender out, often with friends from work, but I wasn’t getting anywhere. I’d visited some spots in Hell’s Kitchen, the East Village and some places in between. I was burning time and money, all in a vain effort to get a bartender to go on a date. Meanwhile, Kerry had been sitting right under my nose for months.

But before you go judging me for targeting a “friend” as my Bartender Date, I should point out that I hardly knew Kerry at all. We had met for the first time ten months earlier at the Del Close Marathon after-party, the same party where I asked out Amy and the same weekend I met Monika. It had been rather a productive weekend for my dating life.

At some point during that night, a woman who refused to go out with me but was intrigued by the project, led me around the party and introduced me to a number of her girlfriends. At one point, I remember meeting three women all at the same time and, with a lot of help from my chaperone, got them all to agree to go out with me. Each of them gave me either their phone number or email address.

Kerry was one of those three women.

Fast forward seven months and I found myself auditioning for UCB’s Harold Night with a group of seven strangers. Though I knew I’d never been in a class or even hung out with any of the people in my audition group, one of the names struck me as oddly familiar. That name was Kerry’s. I couldn’t figure out why I knew her name, so after my audition, I asked her if she was a writer or performer anywhere prominent because I knew that I knew her name. We didn’t figure it out that night, but months later, I realized I knew her name because it was in my phone and in the spreadsheet I kept of potential dates.

Yes, that’s correct — I kept a spreadsheet of women who might potentially go out with me. Her name was on that list, but after not taking her, or either of her friends, up on their offers within a reasonable amount of time after meeting them, I wrote them off as potential dates. When I finally did make the connection between that meeting the prior summer and our UCB audition, I decided to friend her on Facebook. That way, she’d be familiar with my face should I ever need to ask her out. That friend request had come only a few weeks before I was preparing to head out to Kerry’s bar in an effort to ask her out, and aside from our two unremarkable interactions, I’d never spoken to her.

I met Varun outside of the bar and thanked him for being my wing man. We went inside and I spotted Kerry, but as we sat down at the bar and I offered a friendly, “Hello,” it was clear that she didn’t recognize me right away. It took a few seconds for it to register that I was the random guy who’d commented on her Facebook post a couple hours earlier. She remarked on how surprised she was to see me — that my comment had been backed by sincere interest in going to her bar. But there I was — sitting right in front of her, hoping to ask her out.

We ordered a round of drinks and talked about work and women, the standard fare. Kerry was also checking in on us, between serving others at the bar, and was generally very friendly and appreciative to have someone visiting her at work. It didn’t take too long before she asked me to remind her how we knew each other. As previously discussed, our interactions had been sparse and she likely knew my name mostly from Facebook. She remembered the UCB audition when I told her about it, but also asked if I was on some teams that she might have seen or performed with. I told her the teams I was on and that wasn’t it either. Apparently, it was just the audition.

That was when she said, “Wait. Are you the guy with the dating thing?”

Varun and I both laughed and I said, “Yeah. I am.” She seemed to remember it from the internet and hadn’t quite caught on to my reason for being there, so I added, “I’m actually here to ask you out.”

Kerry’s reaction was basically to shout, “What?! NOOOOOOOO!” She was playfully upset with me that I had come into her place of work and held her as a captive audience, with the sole purpose of asking her out on a date, simply because she was a bartender. Varun only stuck around for a drink or two, so he missed out on the 3.5 hours of me sitting at the bar, taking shit from Kerry and her staff, for trying to ask her out.

She immediately informed me that she didn’t date anyone who asked her out while she was behind the bar. It was a rule and it was not to be broken. I figured I would try to anyway. I listened to her tell me time and time again that she wouldn’t go out with me. I listened to her manager tell me it was pointless to try. And I listened to her laugh at my attempts which let me know that my efforts were not in vain. Laughter was my only point of entry with most any woman.

Relentlessly, I asked her out with every chance I had. She ignored me for periods of time. I’d watch her chat with other patrons, toss coasters at them playfully and do her general business tending bar. Only after maybe two hours or more of putting it out there did Kerry finally bite. We were bantering back and forth when she threw a coaster at me in reply to me saying she should date me. When I said, “Come on!” she gestured down at the tossed coaster I’d picked up in my hand. I turned it over and on the back of the coaster it said, “FINE. [555-555-555]”

I reveled in the joy I felt right then. It felt awesome to have finally secured a bartender date after trying for so long and in such a fun fashion. Hanging out at the bar that night had been a very good time. Not wanting to seem like I was only there to get her number, I hung out a while longer, until Kerry’s shift was over. I walked her out and down the block, until we had to part ways. I thanked her for putting up with me and said goodnight.

Two days later, I texted her:

Me: Hey [Kerry]. This is Evan, the bar rat who convinced you to go on a date. Just want to say hi and exchange numbers!

Kerry: Well well well. Look who it is.

Kerry: I’ll have you know, you caused quite a storm in the bar on friday. You’ve already become a bit of a legend [there]. The guy that finally got [Kerry] to agree to go on a date while she was working.

Me: Haha. Well I didn’t mean to cause any trouble but I can’t say I’m sorry.

Kerry: Only a little bit of trouble. But just you wait sir. I got me a blog and a keyboard and you better believe you’re about to be apart of it.

Me: I cannot wait.

That was the story of how I got a date with a bartender for a Saturday night in mid-June. But that wasn’t all, because as we texted in the days leading up to our date, I found out that Kerry wanted to plan the date for me. I think she felt bad for the guy who was surely running out of date ideas. She suggested checking out Burger Joint and we made plans to meet at 8:00 p.m.

IMG_2077On my way into the city, I was struck with a potential dating disaster. My date for the next day, Jamie, texted me while I was on the train to tell me that a family obligation had come up and she had to cancel. It was a difficult pill to swallow not only because I really wanted to see Jamie again, but because the date we had planned was an all day trip to Governors Island for the annual Jazz Age Lawn Party. I was 20 minutes away from meeting Kerry and I was suddenly in need of a date for the next day.

I was dismayed at first, thinking not only of the short notice I’d be giving to anyone I asked out, but also concerned with the fact that if I did miss out on the date, I had only two weeks to plan and execute a ferry riding excursion. My networking and planning faculties kicked in and I immediate began scanning my emails, text messages, FB messages and brain for a potential date.

Quickly, I realized that a woman named Dorothy had reached out to me from OkCupid the night before and I texted her with my proposal. Lucky for me, Kerry ran about 15 minutes late and it gave me just enough time to set things up with Dorothy, who was miraculously available the next day. But you can read all about that in the next post.

Kerry greeted me at the corner of 57th Street and 6th Avenue with a friendly hug and apologized for running late. I told her it was fine because I had really needed the time to get another date to Governor’s Island for the next day. Her response was somewhere between, “That’s a pain in the ass” and “You’re a fool for doing this to yourself.” She was right on both accounts.

As we entered Le Parker Meridien hotel, she asked me if I’d been to Burger Joint before or if I even knew about it. Indeed, I knew about it, but I hadn’t been there before. It was a part of the Midtown New York lore — a down-to-earth, unpretentious burger spot hidden away in the lobby of a decently fancy hotel without so much as a sign to indicate its location. Since I didn’t work far away, I’d heard of it many times, but I wasn’t sure why Kerry knew about it. I learned, after asking her why, that she was from Long Island and her father, who had always worked in the city, had told her about it. 

We rounded the corner in the lobby and ran smack into the line for Burger Joint. It wasn’t too long though and Kerry told me that it would move fairly fast. She also explained to me that I had to know my order when I got to the counter and that they’d be upset with me if I didn’t have my shit tight. I made up my mind and we waited roughly 20 minutes before we were to the front of the line.

Kerry and I both got our orders in without a hitch and we took our beers to the only open table, one that was being vacated as we put our orders in, so we had to jump on the opportunity. She held down the table while I grabbed our food a few minutes later.

The burger was solid — it definitely lived up to its reputation of being a great burger that wouldn’t break the bank. The fries were on point too. And so far, I thought the date was going well.

We covered a lot of the basic first date topics and it became clear that Kerry was a bit of a ball buster which I secretly liked quite a bit.

[If I’m being totally honest — I don’t have many notes on this date and I don’t remember it too well, almost two years later. I don’t mean to say that it wasn’t a good date, or that it wasn’t memorable, but all we did was eat and drink, so the conversations were the primary thing to report back on and honestly, conversations were the things I forget most easily. Also, I feel really terrible that this date has succumb to my habit of poor note taking and shit memory because I went through so much trouble convincing Kerry to go out with me. She deserves the best write up possible, but you’ll have to settle for my minor recollections of the rest of the night rather than the minutiae of our conversations.]

After we had eaten our burgers, scarfed our fries and finished our beers, we needed to vacate so that other patrons could take our seats in the busy restaurant.

Leaving Le Parker Meridien, we debated about where to go next and decided initially that walking west would benefit us since we’d be nearing Hell’s Kitchen, which had many options. I told her that most of the bars in Midtown west were large and impersonal, so I didn’t know of too many great date bars, which are best when somewhat intimate.

Fortunately, Kerry knew a whole lot more about bars than I did because she was a bartender. She asked if I’d ever been to House of Brews. In fact, I had been there a couple times for happy hours with my company. It seemed like an odd choice though, since it was a large, impersonal bar. What I didn’t know was that Kerry knew the bartenders there, and that there were two HoB locations. She was suggesting the one I hadn’t been to and so we walked over and down to 46th Street for some potentially discounted drinks and friendly bartenders.

When we entered the bar, Kerry was greeted right away by a bartender buddy at the end of the bar closest to the door, so that was where we sat. They talked shop a bit and I was introduced to him before he asked what he could get us. We both ordered beers and got back to chatting with each other.

Kerry was very witty and, as mentioned before, really into giving me shit. I think she specifically enjoyed grilling me about OHD and my dating life. Plus, she made fun of my shirt. “What is that, a cowboy shirt? Do you ride horses?” she chided. Yes, it was a cowboy shirt, but no, I did not ride horses. She was playful, not mean. It was the equivalent of pushing me down on the playground. I understood grade school flirtation and apparently, that was Kerry’s main mode of operation.

Finally though, we were able to shift the focus from giving me shit to talking about UCB and improv. We both talked about our journeys with improv and comedy and she dished some UCB gossip. I wasn’t privy to much of it and I didn’t know many performers, so Kerry was able to fill me in on some fun tidbits since she’d been in the scene longer and more deeply entrenched. It was nothing dramatic or terrible, just silly little gossipy things that I’d never heard before.

We also discussed our families and their various dynamics. We got a little more real with each other over the course of this conversation and I’m sure the beers helped a little bit. Also, I’d gotten into leg touching territory. We were both being fun and flirty and I was occasionally touching Kerry’s leg, which she seemed cool with. She was totes cute, so I guess I was hoping it would lead to something more, but I think Kerry was just enjoying the attention and knew that it wouldn’t get me anywhere. What a ball buster.

It was getting late when we finally decided to close out our tab. 

When the check came, I saw that very few of our drinks had made it onto the tab, but Kerry informed me that the way it worked amongst bartenders was that the drinks would be deeply discounted or free and the tips would essentially make up the difference. I estimated what our actual bill should have been and jotted that number down on the final line, essentially doubling the bill we’d been handed. It seemed like a fair trade.

Leaving the bar, I asked Kerry how she planned on getting home and she told me that she would walk to First Avenue and catch a cab uptown. It was a bit of a hike, but I had nowhere to be, so I told her I would walk with her.

We traversed the entirety of Midtown before she finally waved down a taxi. We hugged goodnight and Kerry jumped into her cab, but not without one last snide comment about my cowboy shirt.

Man, bartenders really were impossible.