24 Hours in the Windy City

I think that I did the craziest thing in my life this past weekend.

It all started when I was at my friend L's wedding on the beach in Rhode Island. I was there with our other good friend B. We were sharing a hotel room with his friend E. The wedding was beautiful and we were having a great time. I started talking about how I've been dying to go to Chicago...B and I were talking about when we could possibly go and all of a sudden E says let's just go tonight! E apparantly has some money and was actually willing to buy the three of us tickets as well as book us a hotel room at the swank W hotel for no reason whatsoever. I immediately say I'm in. Chicago + free = totally for me. I was psyched.

He has his "secretary" (does anyone still really use that term anymore) book us the flights and we were only able to get one for 6:30 in the morning. So we continue to enjoy the wedding and the bars afterward. We were pretty typsy and decide to go to sleep for an hour or so. We wake up at 4:30 in the morning and still in a slight drunkin daze manage to get ourselves together to head to the airport. Things were kind of frenzied because B of course didn't have any of his things packed.

We get to the airport kind of late and there is mad chaos inside. I have never seen so many people at 6:00 in the morning. We make it to security - I had decided to carry my bag on. (my bag that included my dress from the night before and a tank top and shorts and pretty much that's it) when i realized that i had all of my toiletries not in the little containers that they were supposed to be in. we are now majorly late for our flight and in a panic i run back over to the check in counter to see if i can get my bag checked. i am able to and i manage to scurry back through security and onto our flight. We have to change planes in Philadelphia and i pray that my bag is along for the ride.

11:30 a.m. - We arrive in the great city of Chi-ca-go. My bag is nowhere to be found. The lady at the desk is no help to me whatsoever and I'm getting ready to wind my hand back to slap her and say I will f--king kill you when B finds my bag just laying all by it's lonesome on another carousel. Slap averted.

12:24 p.m. - Our car service (yes that's correct) drops us off at the W hotel and I seriously am doubting whether they were going to let us stay in such a nice place when we looked like vagrants.

2:06 p.m. - After walking down the Magnificent Mile and having lunch B and I decide to take a much needed nap.

5:40 p.m. - Refreshed we head to Market Days which is the largest gay festival in Chicago and is located in Boys Town. I knew I had landed in Boys Town when the mural on the wall was a Bud Light ad with two guys and the words "Be who you are".
pause - I forgot to add that my friend B and his friend E are both homosexuals and that the caveat to me going on this all expenses paid getaway was that i suck it up and be a lesbian. i mean dress like a lesbian. which i was since all i had in my bag was two wifebeaters (one white and one orange) and a pair of cacki shorts. It was either between that or my party dress from the night before and look like a drag queen.

6:58 p.m. - I am drunk on some mysterious green concoction that the gays keep feeding me. Gay boys are coming up to me left and right like moths to a flame. For a second I feel like Kathy Griffin, but cuter. The bar we are at has this fabulous activity set up where we all have numbers on our shirts and people can write notes to each other. I pretty much threaten this one gay boy into writing me a note which I then flaunt to every person I see after that.

7:16 p.m. - A boy dressed as a lifeguard and nothing but a speedo on comes in and somehow we start talking. I make some comment on how he wouldn't be interested in me. He gets all solemn and almost like the room got dark and there was a light shining on him he says "you never know - things are not always as they appear." i am so confused at this statement and as he is running away i'm shouting - wait! does that mean that you are straight???

7:55 p.m. - A gay man who honestly looks like Frankenstein tells me that I'm beautiful. I am flattered.

8:32 p.m. - Another group of guys and one girl walk in. One of the guys is very cute so me in my all new confident attitude walks right up to him and tells him that I think he's hot. I go on and on about how I know he doesn't care what I think but I just needed to say it. He looks at me and says "I'm straight". I almost fall over for my prayers have been answered. I have found the one straight guy that walked in through those doors.

10:07 p.m. - After doing 2 Irish car bombs I am now teetering on the brink of becoming sick. Thankfully knowing my limits at my age I quickly go into damage control. I immediately order water, down it and need another one. The first bartender was a woman and gave it to me for free, the second time it was a guy bartender and he wanted to charge me for a bottle. I am so pissed at this point and he won't budge. So i decide to accuse him of being prejudiced of straight people and say "what is it because i'm not gay!!??" he then refuses to serve me at all. since i was now standing with my new gay posse they calm me down buy me a bottle of water.

10:45 p.m. - I am still hanging out with my new cute straight boyfriend and we are having a fabulous time dancing because as we all know gay bars play the best music. As we walk from room to room he takes my hand and is seriously getting looks and cat calls from the men as we walk by. Some are disgusted when they see me attached to him, some are proud and shout something like "hold on to him girl". I am weirdly flattered by all of this and wonder how much he is actually secretly enjoying it.

1:22 a.m. - B takes a liking to new cute straight boyfriend's friend so the four of us go out for burritos and i am annoyed that they forget to put guacamole in mine. New cute straight boyfriend and I piss B off by wearing our sunglasses and singing "i wear my sunglasses at night".
I am elated at how the night has turned out and by the fact that I haven't lost anything.

9:00 a.m. - Walk myself to Starbucks and order a Vivanno AND a spinach feta wrap. I know - scandalous. I am on top of the world with how the weekend turned out and want to continue my rock star lifestyle right on into my breakfast order.

11:20 a.m. - I'm on my flight back home wondering how this all happened. It may not have been how I originally envisioned my first trip out to Chicago - but I certainly wouldn't have changed one second of it.