South Side of Heaven (My first trip to Chicago)

So, remember the guy from Halloween from Big Muscle? You know, the guy who I thought I’d never actually see who took me to Capital Grille on the night when I was dressing up as the Old Spice guy. The guy who brought me a rose, which I had to carry through this really fancy restaurant with my pink horse on a stick sticking out of a Toys R Us bag (part of my costume). Well, he lives in Chicago, and he really wanted me to come out and visit. “I have a million frequent flier miles for work, and I have a guest bedroom if you want to stay in there.” Well, I’d never been to Chicago before…

Me: “…yeah, I’m headed to Chicago this weekend.”

Mom: “Oh, what for.”

Me: “A friend moved out there and wanted me to visit. He had a ton of frequent flier miles, so I really had no reason not to go.”

Mom: “Well, make sure you make it to church for Easter.”

Me: [silence]

Mom: “You can find one of those inclusionist churches and take your friend with you!”

Me: “Okay, Ma….”

Turns out Chicago Rose’s miles were on Southwest. I’ve been curious about Southwest ever since I was in college because of their low fares. But their nearest airport was in some Podunk town nowhere near me, and they most definitely didn’t fly into my hometown of Columbia, SC. And until very recently, their nearest airport to NYC was somewhere out on Long Island (mind you, I don’t even like taking the bus to LaGuardia).

image from viral-emailz.com

I’m used to flying on major airlines, so I didn’t even notice that my boarding pass, which I printed out before leaving for LaGuardia, didn’t have a gate number. Or a seat number. Or even a boarding time (just a departure time). And of course, there was a group of like 30 middle school kids waiting at the gate. I had a good 50 minutes before I had to board, so I stopped by the sports bar for a drink, which I made a $22 double because it was so weak. At 35 minutes before departure time, I chugged the rest of my drink and rushed over to the gate. But nobody was boarding. What I did notice was a bunch of poles with numbers and people lined up by them. I had no idea what was going on, so I lined up and figured that the relevant information would be revealed as I needed it.

Turns out Southwest does open seating, and I ended up with an aisle seat near the front! It was a bumpy ride, but that second $5 screwdriver really helped put me at ease.

Chicago Rose was a bit late picking me up, but he gave me a huge hug when he got out of his car. He walked around (in the rain) to open my door for me, and in my seat, I found a dozen red roses. Flowers are so not my style, and roses aren’t the top of my list (if you're gonna spend on something that's gonna look pretty and die, I think leather chaps lilies and tulips are much more aesthetically pleasing), but it was a heart-felt gesture that I appreciated nonetheless.

image from thrasheropera.com

We went right from the airport to dinner at O'Brien's followed by South Side of Heaven, a comedy show at the world-famous Second City. It was pretty damn hilarious with a good combination of political commentary, pop satire and local humor. The show ended around 1, and we headed to Boystown for a drink at Mini Bar, which turned on the lights about 10 minutes after we arrived. We then wandered down to Circuit (official name on Foursquare: Circuit Nightclub and Rehab Cocktail Lounge), which was all Latin besides us with an unexpected mix of either trans-women or really good drag queens.

By the time I got ready for bed back at the apartment, I fell asleep about 3 seconds after my head hit the pillow. Did I mention I was more jet-lagged from going out every night that week than the hour time difference? Yeah.

Click here to check out the night Chicago Rose and I first met.