I Went To A Bar By Myself In New York

This is the final boss of "doing stuff by yourself".

I am writing this from Poetica Coffee on St. Marks Pl and 2nd Ave. The Poetica fans are rejoicing. The Elsewhere Espresso crowd is in shambles. I am drinking a cold brew that is borderline too bitter. 6.3/10.DISCLAIMER: this is my longest blog ever. I highly encourage you to read all the way through because I get kinda serious at the end, which is always fun.

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He had long hair that poked out the back of his baseball cap, drinking a rum and coke. There was a rough around the edges expression about him that made you think “I’d better hope this guy’s on my side if a fight breaks out here at Doc Holliday’s.” His demeanor told you he was at this bar to pass time, watch the game on the TV, get drunk with his buddy, then stumble home. No funny business. No extracurriculars. He was curious, but not judgmental, and he wore his heart on his sleeve.

He was “Garrett”. The 22 year old from Pensacola, Florida, who was in town for the Giants vs Bucs game.

I was sitting on a barstool in the 80% packed bar when Garrett broke the silence in the only way one breaks silence in a dive bar in the East Village when you’re talking to a dude:

“you got any money on this game?”

Garrett was referring to the Alabama vs Oklahoma game on the TV positioned to our left. I let Garrett know that I don’t really sports gamble, but if I did I’m almost certain I would have mistakenly bet on Alabama. In that moment, I essentially signaled to Garrett that “hey, I’m a normal guy. I can talk sports, and I’m not one to take myself too seriously.”

And with that, we were off and running. Garrett asked me how I ended up at Doc Holliday’s, to which I let him know that I was on my own tonight since my roommate had plans. I was just at a dinner with my friend, and I decided I’d check out Doc Holliday’s for a night cap Guinness.

The next 2 hours included top-tier sports banter and general chit chat. At one point, Garrett confided in me that he had cheated on a finance exam in college. Him and his buddies had set up an at-home apparatus that performed magnetic imaging to display the answers to a test on a separate projected screen in their collegiate abode. I said “that’s insane” which is code for “I don’t really know what you just said but I’m going to be nice because I think you’re a good guy.”

The one break in the action occurred when Garrett and his buddy Jake tried to go play pool. First off, such a mistake in the packed bar. But I wasn’t going to tell Garrett what to do.

While I was holding it down at the bar, I witnessed what might be the most perfect encapsulation of dating in Lower Manhattan. I’ll set the scene. Two girls were standing right behind me (again, bar was crowded so everyone was on top of everyone). I didn’t get a good look, but a guy approached these two women and broke the silence in the only way one breaks silence in a dive bar in the East Village when you’re talking to a girl:

”you got any money on the game?” “have you been here before?”

After that, this trio couldn’t have had less chemistry. When the fella announced he worked in “finance”, it all made sense. When they started talking about "WFH policies” at their companies, I knew this wasn’t necessarily the most free flowing conversation of all time. And the worst part of all. This was the toughest part for me to hear. They had somehow gotten on the topic of age. The guy let the ladies know he was 27. And that’s perfectly cool to be that age. However, what was not as cool was that the girls were TWENTY-ONE AND TWENTY-TWO, respectively.

What a perfect encapsulation. 27 year old finance guy approaches two college girls at a bar in the East Village. Hollywood would turn down that script because it’s too obvious.

It’s impossible to know what the intentions were of 27 year old finance guy, and I don’t know him at all, I just know his archetype. But what an incredibly relatable moment. How many 22 year old women have been approached by a 27 year old finance guy in Manhattan in a dive bar?

So after that nightmare, and while Garrett was still trying to bypass the layers of bureaucracy that exist when out-of-towners try to play pool at a locals-only spot, I had another tremendous “dude” interaction at the bar.

Long story short is that this guy also grew up in the suburbs of Chicago and went to Loyola Academy, which is a private catholic school. As a fellow Chicago suburbs private catholic school alum, we hit it off. It was a quick interaction but it was exactly what you want out of a bar interaction with another human. I’ll break it down in a 5 step process:

1. Find common ground
2. Discuss common ground
3. ask where they live right now
4. discuss opinion around that area they live
5. “have a good one brotha”

After that, Garrett came back and let me know that he, in fact, was unable to get on the pool table. I was about to leave when Garrett gave me a parting gift as a sign of brotherhood and respect. He gave me an anonymous Instagram account that was giving out picks for sports gambling that were hitting at a 75% clip.

For those that don’t know, this is essentially the equivalent of extending an olive branch, or getting down on one knee with a ring. Garrett gave me his most prized possession. He gave me “FredWinss”. Garrett said “hey man, I know you’re not gambling, but if you ever do, I got you.” And with that, I shook Garrett’s hand, and I walked out of Doc Holliday’s with the lukewarm and bacteria-infested “Chicken Parm” that I had in a to-go box sitting on the bar for 2 hours.

And that was my night at a bar by myself

It was perfect. I really lucked out by sitting next to a normal and cool dude. But honestly I think most people are normal and cool. New York has a lot of cliches and stereotypes, but I have had incredible experiences with strangers that were exceptionally nice and cool to chat with. Even the 27 year old finance bro seemed like a cool dude despite his absolute dumpster fire of a conversation.

It is yet another example of enjoying time where you are on your own. It goes to show just because you show up somewhere alone, it doesn’t mean you have to be alone where you show up. And in every interaction in the night out, it wasn’t like I was throwing myself at people like a psycho. It all happened naturally. Some people call it happenstance, I call it “aura”. I obviously have a “goated” “aura”.

So take this as a sign to just stop at a dive bar on your way home next time you’re out on the town. It’s tremendously freeing. And when you do it, send me a picture. Also if there is anything else you all want me to do by myself, I’m all ears.

- Jack

P.S. if you enjoyed this and want to buy me a coffee so I can maintain proper caffeination while not having a steady paycheck, send a few bucks to my Venmo. Cheers!