The Perfect Fit

I was shopping for a pair of gray chinos to go with the gray weather in Chicago. Closing date on the condo was approaching and it was starting to look like I would have to take another bartending job in yet another hotel restaurant. While I was browsing the pants online I curiously opened the careers tab just to see what was available. And of course, the Chicago store was looking for a personal shopper for their store. I closed the browser. I had already sent out about a hundred resumes it was time to take the hint. I was officially, and irrevocably a career server. Supposedly when one door closed in life another door opened. In my case it was the door to Nordstrom on Michigan Avenue. I brought with me a fellow bartender to help me pick out an outfit for New York.

What about these? The ones here; she handed me a pair of chinos.

"It's so funny you picked these, I was just looking at them online today," I put down a pile of clothes to hold them up. "You know they're hiring, the company that makes these."

"Really? Why don't you apply," she asked, scooping up my pile. I decided to shelve the pants and the issue and replied with a nondescript sigh. We went to go visit the shoe department where I planned on spending the rest of the day wallowing over the new horse bit Gucci loafers.

"This is just cruel," I said holding up the loafer, "Can't they just stop making these shoes until I start working again?"

"I don't understand. Why wouldn't you do this?"

"Buy these loafers? Lets see they put us about $495 over budget that's why."

"No, this, I mean do this for a living. Shop, pick out clothes, tell people what to wear. I don't understand it's who you are, you're always telling people what to wear and what goes with what. You love clothing and have an almost encyclopedic knowledge of menswear."

"Do you know how many retail queens there are in this town? It's such a small community, almost a cult, and they're not looking to let anyone else in. They want some peppy little teeny bopper who works at Banana Republic to sashay through the door, not me."

"Stop. Why can't you just apply? You can't give up. I'm going to spend the rest of my life bartending, but you don't have to. You don't want to. So what's stopping you from trying?"

"I'll think about it. Hey, you think I can squeeze one more charge on my credit card before they shut it down?"

"No."

The next day I was on a flight to visit my friend Molly in New York. With all the packing and job hunting and obsessing over furniture and man hunting I needed a break from this break from work. Molly had been helping with the design of my apartment so she intended on writing the whole trip off and I intended on putting my anxieties about Chicago to rest. And also, there is a perk to travelling to another city: flirting with businessmen in airport bars.

Anatomy of a Businessman

When it comes to potential hubby material the a-list of my interests lies in one particular group of men. Observe in his natural habitat (airport terminal at 5:30am): the businessman. What is it about these half stale starched specimens that piques my interest so? The reason is simple. I like businessmen for the same reason I like Starbucks: the taste is horrible but you always know exactly what you're getting. For a control freak like myself you can't put a value on consistency. I can walk into any Starbucks in the world and order a double grande nonfat dirty chai with no water and I will get the exact same drink in every location. You can date a businessman from any background or city and know exactly what you're getting and it may not be as exciting or as good a fit as other men but at the very least you know what you're in for.

Lets start with how to spot this special breed indigenous to hotels and cubicles the world over. This is the kind of man that does the same thing the same way every single day of his life. His hair is permanently parted in the same place, he's worn the same glasses for most of his life, he always reads the newspaper sections in the same order (business, sports then world news). Look for the set in dimples established from years of making the same expressions to the same people. Though this man may own many pairs if shoes he only wears two; there's the loafers and the lace ups. This is how you can spot the businessmen native to your area– the ones traveling will be wearing slip on shoes and the locals will be wearing lace-ups. The true moniker of this breed is, naturally, the business suit. As with tropical birds much can be told about these types based on their plumage.

First, think of the suit as a gauge for experience. If it fits loosely he's young and new to his industry, if it fits perfectly he's in his hubby-perfect 30's, and if it's too tight he's got poor taste and probably works as a bank teller. What color is the suit? This is like his mood ring. Never approach a man in a black suit, and never marry a man in a brown one. Blue and grey are day to day, pinstripes are sexually available windowpane plaid is emotionally available and houndstooth means he's kinky. And if the man is wearing mismatched slacks and blazer it means he'll forget your birthday or anniversary or both. Discard men wearing jeans or khakis, they're off duty (or taken). How many buttons does the suit have? Doesn't usually matter, three just means he has a long torso, two means he's average proportioned, one means he shops at h&m and if, god forbid, he is wearing a four button suit he's probably going to take your luggage up to the room.

Second, observe the accoutrements. Don't assume he's single if there's no ring in his finger– they like to take them off, especially at bars parties and on vacation. A better way to tell if they're married is by the cleanliness of their shirt collars. Men are incapable of pre-treating, it's a genetic flaw. Any man wearing a class ring is past his prime. How do I know? His prime was just before he got that ring. Look for men who peak in their late thirties. You can ascertain this by asking two questions. Did you enjoy your high school years? Did you enjoy your college years? You're looking for two nos. People who did well in grade school are bad at life. And anyone who enjoyed their college years didn't go to a serious school or major in a serious subject. If he's wearing a pocket square he reads GQ. If he's wearing a Rolex he reads Jugs.

However, the business men with all their consistency and reliability, lack a certain something to keep me interested. It's best to have your month with them, get a few meals out of it, and let them free to roam the terminals again.

From suits in the airport to suiting on Fifth avenue. I was browsing through Saks waiting for Molly to get off work so we could celebrate my arrival with four straight days of drinking, shopping and eating. I overheard a frustrated man try to explain what he wanted to the sales associate.

"No, a soft suit. You know like a soft suit," the man said.

The sales associate kept pulling suits and was visibly agitated. "So this is a silk blend, and then we have a merino wool, they're both very very soft. Personally I like this one from Jil Sande-"

"No these aren't soft, they're too, I don't know. I saw this guy wearing a suit the other day and it was like floppy or something, really cool."

"Floppy?"

I walked over and interrupted the conversation,

"Armani. He wants the Giorgio Armani unstructured suit. Armani popularized the relaxed suits in the seventies."

"Yeah! The unstructured thingy."

"Thanks," the sales associate said, "Do you work in retail?"

"No." And then I thought about it, "Not yet."

After my reaffirming shopping experience in New York I decided to apply for the personal shopper position as soon as I got back to Chicago. On the train ride home from O'hare I checked my OK Cupid (a misnomer really, should have been called so-so cupid, or stupid cupid) To find a message from a handsome thirty-something beardy actor/writer on the north side. Things were looking up. Within a week I was scheduling my first interview and my first date. And I'll save you the week of soul searching and anxious phone watching: I got a second interview, and the second date. I was so excited about the news of making it to the second round of interviews that it really put me in the romantic mood. So at dinner my date suggested we go celebrate with a drink after dinner. We wound up at the Granville Anvil, which is pretty much as horrible as it sounds. The seediness of this bar is matched only by Second Story bar on Ohio st and a bar called Dick's on the border of Indiana.

It became apparent after his seventh whiskey that my date was intoxicated so I decided to walk him home and invite myself in to spend the night since it was late and snow storming. I was prepared for a snowstorm-- a shitstorm, on the other hand, I was not prepared for. When I walked into his apartment I at first thought we had maybe walked into one of his neighbors' crack dens. It was beyond messy. It was Somalia. It was a fourth world country. 

"I'm just going to use the bathroom," he said, and hopped, HOPPED, over a pile of clothes and other things into the bathroom. I trudged into the bedroom and if there wasn't several feet of snow on the ground in Roger's Park I would have hopped the hell out of there. Walking into this apartment is like turning the lights on too quickly in the morning. Your eyes need time to adjust to it. By the time he was finished in the bathroom I had just about adjusted to the mess when I saw a bra hanging from the top drawer of his dresser, which was a very unusual piece of furniture in this apartment given that it was empty and all the clothing was on the floor.

I held it up as he walked, or hopped, through the bedroom door.

"Do we need to talk about this?" I asked, holding it up.

"Oh, that."

"I mean I'm less troubled by the fact that you have girls over and more troubled by the fact any any woman would remove her clothing in this apartment."

"Ha-ha, my place is messy. I just closed two shows."

"Well they must have run longer than Cats because this place is a disaster."

"The bra is from a sketch comedy show where I dressed up as a woman." I flung the bra in the corner. I made a space for myself on the bed.

In every relationship there is a bra. There is always some 'what the fuck' moment that makes us reconsider. The real test of a romance is what to do after we find the bra. The next morning I woke up in his apartment after he had left for work. I was impressed with his willingness to leave me alone in his place. It was a good sign he was willing to commit although maybe he suspected that the mess would prevent or deter all snooping efforts. And it worked, in a very uncharacteristic move I decided to leave without looking through all the drawers. One bra was enough for this visit.

Later, in a phone call with my mother, I explained the plight. I can't date a slob, I alphabetize my dress shirts by designer. Why would the universe do this to me? Why send me a handsome sweat great guy with a job and his own place and then do this to it. It was like an overcooked cut of prime rib. It could have been perfect, and now I wondered if his condo was something I could digest. All this time I've catalogued all of the dump-worthy flaws in men into an encyclopedic tome of would-be hubbies. And now it was time for me to stop looking for negatives. There was too much right for me to throw in the towel, or in this case, throw the towel on the floor. At least I didn't have to worry about fighting for closet space, I don't even think he owned hangers.

Back downtown, and in the comfort of my mess-free apartment I was performing a special brand of feng shui: how to arrange your apartment when you have a Skype interview. I positioned the laptop at a 90 degree angle to the window so as not to create backlighting, put a lamp behind the computer to create a soft warm glow. I moved the bookshelf and side tables around to create a harmonious and balanced backdrop that wouldn't draw attention away from me but also wouldn't be stale or boring. When it came to webcams I was the Nate Berkus of Skype interview decor.

It seemed like everything was wrapping up nicely. I had a new boyfriend, a new condo, and after one more round of interviews a new job. It was funny how the universe tied things up this way, made a big mess of things and then somehow cleaned it all up for you too. I thought back to all of the bad apartments, bad jobs and bad dates I'd been on. Suddenly none of that seemed important. While I was obsessively analyzing my life an a amazing thing happened: I actually lived some of it. That was the thing about shopping, sometimes you didn't find a thing to wear and sometimes you found the perfect fit.