Woops. I’m in Chicago. Can you guess why? I’ll give you a hint. See the Seven Day Love Affair. Where was he moving? Woops. Chicago. Woops. At this point it seems silly to keep his identity anonymous since he’s become a major character and knows I’m writing about this, so I will henceforth refer to him by his name, which is Tyler.

Late Monday evening, amidst talk about experience whore-dom, Tyler suggested I hop on the next plane to Chicago and come meet him. He has a handy little perk that allows him $60 roundtrip buddy passes from Denver to Midway; chump change when you consider most people spend that on dinner and a night at the bar (or, uh, just dinner OR just a night at the bar). I agreed to see if I could come Wednesday morning for 48 hours. Tuesday night, about 4 hours before I needed to leave for the airport, I booked the ticket.

I’ve taken spontaneous trips before, but flying 1000 miles to hang out with some dude that I met online and was supposed to have just ended a seven day love affair with is somewhat crazy by anyone’s definition (including mine). Apparently, I was lying when I said I wanted this neatly buttoned up on my dating resume. Apparently what I meant by that was I wanted to make rash decisions and be eternally suspended in some weird gray area. Apparently I have no willpower when it comes to certain things. Cool. And okay, those of you who have known me forever are rolling your eyes at how NOT surprised you are. Fine.

I arrived in Chicago a little before noon and realized what winter temperatures in this place feel like as I plodded up the jetway. I’ve visited Chicago in the winter, but I guess it was during a heat spell. This was like the arctic tundra. Since I’d thrown things in a bag at about 4 am, I wasn’t appropriately prepared for this event; I didn’t have socks, for instance. I learned why people complain about the Chicago winter as I stood without socks waiting for the above-ground train. Not good times.

Tyler’s school is located on the IIT campus in an area of Chicago where the administration actually tells the students not to venture (specifically, they’re not supposed to venture south of 35^th street… so of course the first thing I wanted to do was venture south of 35^th street). Tyler picked me up from the train and then romantically scanned me into the dining hall for lunch. The dining hall felt like a totally normal experience when I was a college student, but being 3 years removed from it (and about 5 years removed from the days of actually eating in the dining hall) had me reflecting momentarily on just how weird the whole concept is. Welcome to Taco Thursday… it’s like summer camp.

The afternoon passed mostly uneventfully other than my brief reminder of roommate politics in, uh, social situations, and then I browbeat Tyler and his friends into watching the State of the Union address and drinking bourbon. In order to execute this plan, we had to hit a liquor store on the aforementioned 35^th street, famous divide between the semi-safe and semi-sketchy. Though the three block walk threatened to eliminate my extremities due to frostbite, it gave me a taste of the local neighborhood, which was full of check-cashing spots and ethnic diversity. We purchased Jack Daniels in a store that kept everything behind the counter, presumably to prevent theft. I was reminded of my old neighborhood in Brooklyn to some degree, except that my old neighborhood liquor stores also had a cage for the clerks so they didn’t get shot. Yay, gentrification.

We headed back into the fray only to immediately pass a soul food place. I don’t remember exchanging words on dinner plans; we just made the turn to the right into Mama Lou’s because it seemed like the only thing to do on a freezing cold Chicago night when the rest of the plans included bourbon and the State of the Union. The man behind the counter spoke and worked slowly, and I noticed some sort of fungus growing on one of his fingernails. Probably not the safest bet for food in general, but definitely a good sign for soul food. We waited patiently (?) as the woman in front of us, clothed head to toe in the color brown, ordered her dinner, making conversation with everyone around her, including us.

“Say, you kids go to school at IIT?”

“Yes,” we (I) lied.

“Figured. Anytime you see white folks round these parts, they go to IIT. Least ya enjoy our food. Where ya from?”

“Colorado,” we replied in unison.

“Coloradians! Coloradians in the HOOD! You be sure and remember that. You in the HOOD!” She laughed then to herself, and took her bags, walking back out the door and into the winter, and we were left to contend with the choices in front of us, which had suddenly become more appealing now that this woman had given us permission to view them as authentic ethnic foods from the Southside.

Chicken smothered in gravy seemed to be the way to go, coupled with garlic mashed potatoes and macaroni and cheese and a good healthy helping of peach cobbler. After a treacherous return trip, we were burying our face in huge chunks of messy chicken and licking our fingers. No dainty eating for this girl. I may or may not have eaten the gravy with a spoon.

The State of the Union viewing was, naturally, a group event, and the more bourbon we consumed, the smarter we got, so I ended the night in a political discussion with Tyler’s roommate about the implications of global warming on democracy. This made me more than a little nostalgic for my college days, which is probably the last time I got drunk and discussed political issues for hours on end. I’m sure that wasn’t annoying for others in the same room at all. Oh, liberal arts. How I miss you.

The next day’s events aren’t exactly story-worthy, other than a trek up North that was supposed to be for blues but ended up being for weird fusion sandwiches made of Asian noodles, hot dogs, meatballs, and other things that shouldn’t have worked together but did.  Over our surprise feast, we discussed the implications of my journey, affirming the fact that we’d achieved an uncharted level of honesty with each other and that neither of us wanted to give that up for anything.  It was a strange conversation, simultaneously acknowledging the potential of our future while very much defining that we were in a gray area.  While continuing anything should be almost impossible given the circumstances, the entire relationship is unnaturally natural; there’s no accommodating, no compromising, what we want is simply compatible, at least right now. In a sense, it allows both of us to have an incredibly selfish relationship, living how we would anyway, while knowing that it’s just that quality that the other appreciates.  And that brings me back to a topic I’ve explored for awhile now:  are we really looking for “The One,” or are we looking for the person who’s going to accept our selfish desires and accommodate them while not sacrificing their own?

And then we were one of those gross PDA couples that I oft make fun of on the train, not overtly making out or anything, but stealing kisses when we thought no one was watching, behaving like teenagers or the plot of a romantic comedy. Weird. Gross. I don’t like romantic comedies (uh, except for When Harry Met Sally and Love, Actually, obv), and I don’t like PDA couples. Am I going soft? That idea is disgusting to me.

Delightful and possibly implication-heavy as the two days were, there was no out-with-a-bang-let’s-confess-our-love last interaction. In fact, our last night was spent in strangely comfortable silence: Tyler reading Plato, me working on responsibilities I’d shirked and talking to friends via gchat while Billie Holiday played from the crappy speakers of Tyler’s computer, both of us exploring displaying some unbecoming habits in front of each other.

The risk Tyler and I ran throughout this whole event was that there would now be pressure to take a next step, whatever the next step to something like this is. After all, not even two weeks ago we’d discussed not hoping for any kind of a relationship. Flying to Chicago 10 days later is not exactly keeping the seven-day love affair a seven-day love affair. Would the shift in the definition of the relationship also shift the interaction, sending us backwards a step to the ever-present, albeit minor, awkwardness experienced in the get-to-know-you phase of a relationship? Would this somehow change the rules of the game, thrusting us into a complicated long-distance relationship we’d been adamant about avoiding?

Well, no. As for awkwardness, it just doesn’t exist. Somehow, Tyler and I’ve managed to skip right over the whole skeletons-in-the-closet-and-let’s-not-tell-each-other-everything-we’re-thinking phase. I chalked that up to our one-week limitation before, but two more days in uncharted territory proved it hasn’t gone away. There’s nothing in my past, present, or future that I mind him knowing, including other men I’m seeing. He’s become a confidant on a level reserved for just a few people in my life. It’s a strange place to be, a place I reach rarely, and a place I’ve never reached with someone with whom I have some semblance of a romantic relationship, mostly because my desire for that person to think I’m cool gets in the way.

Don’t misread here; I’m still not exactly banking on this interaction growing wings and taking some silly flight to Frank Sinatra’s moon. Lord knows I love an intense relationship (I can already see the comments forming in ex-love’s brains). Lord knows I love human connection. So it’s probably not really out of character at all that I went to Chicago for two days just to see where we were. It’s where we are that’s a new one for me. Somehow, our horrible timing and circumstances are what make this thing work: there’s no head vs. heart here, and there’s no pressure to make this black and white, planning for some happily-ever-after future in which we’re simply racing to the next step in conventional relationship terms. I’m getting my ideal situation: instead of fighting to keep things in a gray area so as to circumvent brutal honesty and keep living my life, I have a purposely defined gray area that allows me to keep living my life, except that I don’t have to circumvent the honesty part. Your guess is as good as mine as to how this turns out; anything’s possible at this point.