The Time I Was a Fancy Hobo in Chicago

I'm not a particularly fancy person. Most of my clothes are from Target, & I still eat ramen for dinner sometimes. I swear a lot & frequent dive bars. I don't know makes for a fancy person, necessarily, but I think most of those things disqualify me.

In May, I went to the fanciest event I've yet been to: the black tie wedding of Tom & Anna, two friends who I met at Bloggers in Sin City last spring, which took place in downtown Chicago. Many, many texts were exchanged in advance of the event, as my friends & I decided what to wear, when to arrive, where to stay, & other such vital details. For my part, I tried on no fewer than 60 gowns in an attempt to dress myself in a properly fancy manner, scouring every Macy's in the Greater Metropolitan Area for the perfect formal frock. I purchased six gowns online, all of which I returned when I decided to go with my top choice, the navy gown you see here, finally located at the Macy's at Tyson's Corner. Whew.

The weekend of the big event, four of us went last-minute shopping for sparkly heels & appropriate clutches, & we got our hair & makeup done by professionals who know hair & makeup better than we do. And when the time came for us to celebrate with Tom & Anna as they said "I do," we all felt - & looked, if I may say so myself - like pretty, pretty princesses. The wedding was a fabulously good time, the newlyweds were the happiest, & I have never felt so fancy in my whole life.

And then.

My plan was to stay in Chicago for a few extra days to explore the city & catch up with friends who live there. Unfortunately, I was slated to spend each of the next three nights at a different apartment, which meant lugging my suitcase through the streets of the Windy City - not exactly a tourist's dream. In a moment of brilliance, I decided to ship my suitcase back to D.C. before me; I'd set aside a few things to use during the next few days, & my heavy suitcase would be waiting for me D.C. when I arrived home! The kind folks at FedEx were delightfully helpful in making it happen, & I was quite pleased with myself for coming up with the idea.

While it was a smart plan in theory, the reality went less smoothly.

I put some clothes & toiletries & an extra pair of shoes into a Men's Warehouse bag - a paper bag, you guys - which, laden with all my things, turned out to be heavier than I'd bargained for. And though I didn't have to tote a rolling suitcase around the city with me, I still had to take the paper bag everywhere - you know, like a goddamn hobo. Needless to say, I didn't end up doing much sightseeing, after all. I shopped on the Miracle Mile, spent hours in a busy Starbucks writing & people-watching, sat in a park watching the season finale of Grey's Anatomy on my iPad. I did bar trivia with Jess, went out to dinner with Ethan, caught up with Kevin - & I brought my paper bag with me to each of them, carrying all my worldly belongings (OK, that's dramatic) everywhere I went.

Flying without luggage was a delight, as was returning home to find my suitcase waiting for me inside my apartment. But, um, maybe I'll plan ahead next time & bring a backpack with me - or better yet, a bindle.

I think the cigarettes really make the shot, don't you?