Weekend Anxiety

Kiss the Bottle
6 min readDec 12, 2022

I didn’t have a great weekend. It started off alright. I met up with my girlfriend at the Blue Line Bar and Grill on Friday. We had been there before on one of our first dates. She came back to my place that night for the first time. The first time I entertained someone else at my condo.

I got to the Blue Line Bar and Grill a bit earlier than her and ordered a blue cheese martini, extra dirty. I was hesitant on ordering the drink because it had been two weeks since the last time I drank. I rationalized the drink because my head hurt, I spent all day reading legal papers and the $55,000 I made on Thursday was evaporated from market volatility in a stock that no one else seems to understand. By the time my girlfriend got to the table I had already finished half the martini and was planning to order a second one.

The chicken pot pie I ordered for dinner is one best chicken pot pies you can get in Chicago. It comes out in a huge dish and the breading on the top expands like it was blown up by helium. Crisp, homey and hot to the touch. I ordered a second martini when the food came and guzzled it down. Straight to the face.

We headed back to my place afterwards and watched 45 minutes of the movie Superbad before our clothes were tossed to the ground. I’m not sure how we got there but we ended up tumbling down the hall into my bed. Afterwards she told me some nice things about me that she likes. She is really good at using words of affirmation and I am beginning to think it might be one of my more valued love languages. Other women I have been with in the past didn’t compliment me much on anything and it has been nice to hear things she likes about me.

The night was great. But when we woke up in the morning I was anxious and wanted to be left alone. When sitting on my couch having morning coffee I could feel sadness and anxiety. I made up some stuff about how I needed to get a lot of stuff done around the house and called her an Uber ride home. Post alcohol anxiety kicks my ass. I haven’t felt like this since Thanksgiving when I binge drank everyday. My old life of weekend drinking hangover mess came spiraling back. Fuck.

After she left, I spent most of the day watching King of the Hill and playing the new Pokémon game. I did manage to go to the gym for a bit which was helpful. At 1pm I took a nap and woke up at 2:00pm to rush to the blue line. I was meeting up with my good friend and all his friends from Dallas at the Christkindl Market in the Loop. Him and his wife were having their annual Christmas party that night and I wasn’t going to miss it, and planned on binge drinking heavy that night.

The Christkindl Market is a shitshow of a mess. I don’t understand why anyone likes it. It is a clusterfuck of stupid Americans looking at stupid Christmas goods made in Asia. There are so many people you can’t even walk. The only good part about the Christkindl Market is the $10 mulled wine and beer. But even then, they only accept cash so you have to wait in a long ass line at the ATM to pull out $20 worthless dollars. I don’t think anyone likes it but we all go to it anyways every year because it is just something to fill the gaps of time with.

I drank two mulled wines while catching up with some of these friends from Dallas I hung out with in the Summer. Let’s talk a bit about who these people are.

My friend from Chicago is a very social creature and extremely good at making friends. Most of these people are his college buddies from SMU. One is a salesman who makes $500k per year. Another guy is a dude who sells ad space for football stadiums. Both of their wives are former Dallas Cowboy Cheerleaders. There was another data scientist who was desperate to get laid that night. And two other younger friends from Chicago who love doing coke.

After the Christkindl Market we headed back to my friends penthouse on the 59th floor of his high rise to get the party started. More people poured in as I poured more drinks down my throat. I popped and Adderall and started rolling.

One of the guys married to one of the Dallas Cowboy Cheerleaders got sloppy drunk and was making a fool of himself pretty early into the party. His wife seemed pretty annoyed at her fat drunken mess husband. Throughout the party she kept flirting with me and touching my back with her hand.

I was the only guy there without a significant other and everyone knows I just went through a divorce. It is a totally different dynamic being a recently divorced guy surrounded around married women. When you are married and have you wife around you women don’t flirt with you. But when you are on the open market the dynamic totally switches. You become a hot commodity in their eyes and a type of game to see how much they can flirt with you before their husband’s notice. If I was aggressive enough I probably could have slept with this chick when her fat husband passed out.

By 11pm I was eight drinks in and actively smoking vapes. I started to feel sharp pains in my gut. Like pains so bad I couldn’t drink or eat anymore. Guzzling water became my drink of choice. I talked to a girl I haven’t seen since summertime. She is in the process of decorating a $65 million house in Palm Beach for her job. Her smile is still as beautiful as ever.

I peeled out of there at 12am. While waiting for my Uber I bummed a cigarette from a couple of Chinese guys. Smoked 1/3 of it and finished it on my balcony as the rain drizzled down. I watched two of my neighbors from the building across the street cleaning up a party they were having as the cigarette bit to the filter. Both were Asian women. Why do I only notice Asian women now that I am fucking one?

I woke up the next day with terrible anxiety. I accomplished nothing besides getting a haircut and going to the gym for a quick session. I laid on my couch and watched more King of the Hill while playing Pokémon. When the evening approached I called my girlfriend and told her I wasn’t feeling that great and cancelled our unofficial plans. She wasn’t even upset at all which was great. I don’t know how to piss this lady off but I am sure I will eventually.

Beef stroganoff was made for dinner and I wrote my investing newsletter for Monday. I attempted to read but ended up falling asleep early. Overall the weekend was wasted with nothing accomplished.

I am a pretty motivated person and goal oriented. I became a millionaire before age 30 and built and sold a business for a seven figure deal after becoming a millionaire. I landed a job at a hedge fund without going to B school and compete with top analysts. Despite these achievements, my personal self has been held back by drugs and alcohol.

The two weeks I didn’t have one drink or substance was the longest I have went in years, probably a decade or more. I felt great and more motivated than ever. My mood drastically improved. I was energized and didn’t feel the nihilistic apathy I usually feel. It was an amazing feeling what zero substances did to my mental health.

I am going to be focused on being as sober as I can be going forward. I’m sick of feeling like shit on the weekends. Accomplishing nothing and feeling anxiety all weekend is not how I want to live my life. I’m trying to imagine how much I could accomplish if I wasn’t high, drunk or hungover 30% of the week. I’d like to explore that portion of myself this year and see where that takes me. Let’s see if I can do that.

Three things I am thankful for:

  1. My network: I know a lot of well connected and successful people from working at a hedge fund. Today I went out for lunch with a guy who builds, manages and operates high end real estate developments like office buildings and casinos. It is nice talking to these individuals and having them as a sort of mentor base.
  2. Meeting new people: This past summer I have met a lot of new people. Became friends with people I never thought I would be friends with. I am thankful for these connections and what they have provided me.
  3. Books: I love to read. Being a big reader is the biggest reason for the position I am in today. Without books I would have never taught myself how to be an investor or a writer.

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Kiss the Bottle

There is a Japanese term: Mono no aware. It means basically, the sad beauty of seeing time pass — the aching awareness of impermanence.