I knew in my heart that my decision was already made. But, being risk adverse, I felt the need to do further research to confirm that this was a good decision. I had some doubts in myself. What if I wasn't able to hack it? What if I ended up a shut in, scared to meet people? Some close friends helped me work through my anxieties and helped me to realize that at the very least, it would be a great two-week working vacation. What did I have to lose other than a little bit of money? Sold.
Flights between Los Angeles are surprisingly affordable if booked within a reasonable timeframe. I've paid more, on several occasions, to fly to Vegas. I had the foresight to book a morning flight that didn't require getting to the airport at the crack of dawn. How odd to fly and actually check a bag - something I never do... but with 2 weeks and unpredictable weather, a full office to support and just plain old stuff, I was overflowing.
The flight was uneventful. Emergency exit row makes life much more bearable. About halfway through the flight, I started chatting with the couple next to me and told them the purpose of the trip. Their excitement grew for me as I divulged more details. Wintering in Los Angeles, working from anywhere... it all added up to the same question I get over and over - why would I NOT do it? We talked about the idea of blogging about my experience, with the eventual goal of parlaying the blog into a book deal and eventually a movie... Sounds nice, right? And then we ran with the thought that I should move to a different city every year or 6 months and chronicle the experiences there... additional books, additional movies... the cash was just rolling in. We brainstormed on a list of cities: New York, Miami, San Francisco, Las Vegas (I'll pass on that one!)... It was a fun conversation, but at the end of it, this adventure was very specific to the city of Chicago for me and that other cities that I had visitied had never charmed me the way Chicago did.
Landed and took the train into town. The apartment was a crap shoot. Wasn't sure if my corporate housing service, which was based in Florida (!) But my fears were put at ease quickly. The building is only a couple years old. I would later find that there were a ton of amenities - a full gym, game rooms, regular activities scheduled, 24 hour door service... it was all I could ask for. And the building was filled younger folks - definitely not a family atmosphere. Plus, it's pet friendly, so I would see numerous dogs of varying sizes. Made me miss my dog at home, Happy. Apartment was small but completely functional. A quick check of my biggest requirement - the internet... very strong! We're in business!
Quickly unpacked and got ready to meet up with my one acquaintance in the city - my welcome wagon. Bill is a friend of my best friend. I had met up with him on my first trip and was looking forward to seeing a friendly face. I got ready and headed out to a bar called the Green Door. A short cab ride from my place, the Green Door is said to be the oldest bar in Chicago. It's building was in the great fire of 1871 and still pitches to one side. It's a local pub - exactly up my alley. Bill arrived with an old college buddy, Todd. We sat and got a drink. Apparently I was late to the party... seems Bill had started his drinking very early and was tapering off with beer (he's normally a hard liquor man). We had a few drinks and decided to move on. Bill had a friend in from Indiana - a doctor he had previously worked with. His friend was in town to meet a girl he was being set up with. Turns out that she had brought a friend on the date and they wanted to go dancing. Sights set on going to a club.
Clubs really aren't my scene. I prefer to sit and actually hear the conversations you're having. But, it was my first night and I wanted to see anything and everything. We headed to Underground - what was described to me as a very "Vegas" club. We arrived and there was a line. The bouncers were extremely unfriendly and curt. The two girls turned out to be asian... Asians are a bit of a novelty in the midwest - certainly compared to Los Angeles. So we girls pushed to the front of the line and tried to work our charm. Sadly, we had no luck and being far too old to wait more than a few minutes, we moved on to another lounge-y establishment, called Cuvee. Arriving at about 11:30, the place was empty - it was Saturday after all... We had a round of drinks and slowly the place started to fill up. The girls were from San Francisco and very typical of that area. Cute, professionals, a bit standoffish. They were pleasant enough and we all chatted about those things you chat with people about at a club.
I went out for a cigarette and as is always the case, this is where you meet everyone. You can hear conversations and there's just a comraderie among smokers that's universal. I met some guys from Macedonia that had been in Chicago for a few years. I gave them the story and they were encouraging... but the winters! This is the disclosure I get from everyone I encounter. The winters are brutal. It was a pleasant conversation and he introduced me to his 5 guy friends. We exchange introductions and head in from the cold. The club is hopping at this point and getting quite loud. We continue drink and chat. My lightweight status with drinking is slowing my evening down. I contemplate leaving the club, but the others convince me to stay. It's a scene and the people watching alone is worth the price of admission - a sea of white people. The girls are all in short dresses and sky high heels. There's some dancing on the banquettes, but generally, it's a pretty tame scene.
The evening whiles away and it's getting late. At this point, I'm starving, but no one is interested in eating. The girls are the first to leave... I think Bill's friend was very underwhelmed by his date. Personally, I think he can do much better. We leave the club and Bill is very drunk. We get in a cab and we go to Bill's place. He plops down on the couch and mumbles something about watching TV. I'm tired. My feet hurt from my 6 (yes, 6) inch heels. I watch TV for a while and then try to get Bill to get up so I can put him to bed. He refuses. I sit back down and doze off a bit. I wake up with no idea of the time. I try one more time to move Bill, but he isn't budging. So, I left him on the couch and left his place. It's 4:30 in the morning and the street is a ghost town. I wonder how long I should stand there before I walk somewhere or go back in. And somehow, magically, one appears and I'm wisked home. I crawl into bed as the sun is coming up. I love this town.
It wasn't a completely wild evening, but it was fun. And I know that it's just the beginning of a great adventure to come!
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