"That one doesn't like to work"

After my terrible return to New York City, I was able to leave again but not for anything fun. I was relieved. The last thing I needed in my life was more fun. I had about 2 weeks of work trips for conferences--the first to Chicago and the second in Boston. I had never been able to travel for work before and I felt very professional, despite how I act on weekends. So a couple days later, I had to forsake going out on a Friday night so that I could catch a 7am flight the next morning. I had been to Chicago once before a couple years ago for St. Patrick's Day. Except I didn't get to see much of the city, since my friend BK and I had drank too much cheap gin the second night there and couldn't drag ourselves out of bed for the festivities since we were too busy puking. This trip proved to be the exact opposite. I did nothing but work for four days and at night holed myself up in my hotel room, reading or eating room service in my bathing suit. I went out to dinner one night with my boss and her hilarious gay friend but that was pretty much the only socializing I did, aside from the last night.
I was ready to be out in the world again and eager to see some of the city, since our hotel was in an area with nothing else around it. So I decided to go out with Chi Friend. He was the only person I knew in Chicago and knew was a loose term. He was the guy I had met a couple months earlier at JM's friend's apartment in Williamsburg. I didn't actually expect to hang out with him but we had exchanged a couple messages on facebook and I was ready to have anyone show me around really.
He gave me instructions on how to get to the Wicker Park neighborhood on the El train, so I of course hopped in a cab and expensed the whole thing. It was a bit strange basically meeting a complete stranger but I just started to blab about god knows what as we walked to a nearby bar. We sat outside on the patio at my insistence, even though it was roughly 255 degrees outside. We chatted about things, such as how he wants to move to New York and the different neighborhoods of Chicago. He was a total hipster and we were apparently in a pretty hipster area, and about to migrate to a complete hipster neighborhood, when we took the train up to Logan Square. We walked to a brewery/bar he had talked about and I felt like I was back in Bushwick. I definitely stood out in my green sundress and Michael Kors sandals but I had had a few beers and did not give a shit. All of the beer taps at this place were different colored fists and I was having a hard time deciding which to get. As I made an assessment I said to him "I bet the black one is really dark beer". He looked relieved and said "I thought you were about to say something bad like 'I bet the black one doesn't like to work a lot'". I then died and decided that this guy was awesome in my book. We then opened up and exchanged some more personal stories. My favorite from him was how he went home with a girl his first week in Chicago when he was really wasted. She had to leave for class (yes class) the next morning so after she was gone he threw up all over her room. After he had cleaned it up he got lost on the subway going home. When he finally figured out his way, he had to get off the train and walk the rest of the way home because he was too sick. He started to cry and then threw up on the sidewalk before stumbling into his apartment. Classic.
Our final stop was a bar where you got a free pizza with a beer, much like Crocodile Lounge in NYC, but much nicer. I was pretty drunk at this point, laughing loudly at everything and having a grand old time. He didn't seem to mind but I had my guard up in case he tried to take me home. After beer/pizza we both decided to split the Jameson ice cream, which was so strong that I needed to chase each bite with water. Probably the last thing I needed before my early flight back to New York the next morning. Because of this I had to call it a night early, which may have saved me. Luckily he didn't try any moves and I'm sure he had his own agenda since he knew I had to go back early. I found out a couple months later that he is kind of a player and a liar (he claimed that night he had only done coke once but he was apparently a cokehead back in the day, he also said he barely knew JM's friend but they had grown up together in Michigan) but he showed me a good time that night, so water under the bridge.
I spent the next day flying back to New York and then doing my laundry at home. I had one day at work and then the next day we were leaving for our conference in Boston. My one day back at work turned out to be pretty much a joke. We worked for half the day and then it was time for the annual Sales and Marketing Department boat outing. That's right, a sailing trip on the Hudson River. I was pumped. Unfortunately my boss and coworker absolutely love to just work work work because they both have husbands that are never around and weren't as excited as me for the boat trip. In fact we almost didn't go because they thought that we have too much work in between the conferences. I was appalled but luckily it was mandatory and we all had to go. So off to the sailboat we went, in company polos that we were forced to wear that made us look like Best Buy employees. We set sail on the boat and I slowly started to get nauseous. FML. All I wanted was this boat trip and now I felt like I was going to vom in front of everyone. And I was stuck on the crappy side of the boat with the weirdos from Data Processing. They soon got into a heated discussion about whether aliens were real and I took that as my cue to teeter carefully to the other side of the boat where cooler people were sitting. I plopped down next to my Work Friend and concentrated on not vomming for the rest of the ride.
Luckily there was food and drinks waiting for us all at the Frying Pan when we disembarked and I immediately felt better. We had our own private section of this boat bar and we weren't there 15 minutes when the Sales team decided to start an impromptu flip cup game. I was pleased as we all know I love flip cup, but I knew I couldn't get too out of control since this was a work function. We played a few rounds, and I was awesome, as I always am. This surprised a lot of people since I tend to be very quiet in the workplace and not reveal my real personality. I'm sure the whole Sales department thinks I am a huge nerd, or at least did until my flip cup victories. There was another company work function at the other end of the boat bar also playing flip cup and they challenged us to a game. I was one of the ones selected for the "dream team" due to my skill and we beat them easily. Apparently my big boss was very impressed with my performance and I later caught two of the Sales guys impersonating me playing--they would flip the cup on the first try and then yell out different library terms like "proximity operator" and "boolean searching" and smack the table.
There was a small break and that is when I spotted him--my old roommate. There was another private party at the front of the bar, filled with a bunch of weirdos and he was actually part of it. He looked like a ginger Michael Moore wearing a baseball cap and a blazer. His red hair had gotten longer and he had chunked out big time but it was definitely him. I'm sure he must have spotted me as well but we didn't say a word to each other. The last time I had seen him was the summer before, exactly a year ago, when I had thrown my keys at his face and left that godforsaken living situation for good. So we weren't exactly on good terms but true to creeper form, I had recently discovered him creeping my Linkedin profile. It was jarring to see him out,  as bad as seeing an ex, but it made me feel better to think how far I had come since escaping him. I was now working a real person job and going out drinking with coworkers, just like everyone else in New York.

Flip cup had resumed and this time my boss and big boss joined in. Things were getting rowdy and beer was everywhere. My Work Friend would scream "That was money!" every time the big boss flipped the cup and my actual boss was pretty wasted. So wasted in fact that at one point she screamed "You trash-talking mother fucker!" to the big boss. I got to witness that and also bond with most of the Sales team, who I hadn't really known before. And since we were leaving for Boston, I didn't have to face any of them at work the next day!