The Time I Had To Take My Boss Jeans Shopping

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I was living in rural North Carolina at the time and working for a congressional candidate. My job title was “director of finance,” which meant that despite having a prestigious sounding résumé line, I pretty much just spent most of my days on the phone with people quite literally begging for money, and most of my nights throwing parties at random strangers’ homes where I would take a break from begging for money over the phone and, instead, beg for it in person. The funny/sick part about my job was that my candidate was actually obscenely wealthy, and he wasn’t even originally from the district in which he was running — though, to be fair, neither were any of his staffers. He easily could’ve funded his campaign if he wanted to, but he didn’t. So instead, we preyed upon the struggling blue collar workers and semi-wealthy old people with words like “change” and “hope” (not hope and change, mind you) and the promise of lower taxes. We were frauds, really. True carpetbaggers in every sense of the word.

Despite the candidate’s arrogance, though, I really liked him as a person. He was originally from the People’s Republic of Massachusetts, and after earning both his MBA and JD, he headed on down to the land of the pine…and cheaper real estate. A self-made man, he’d married into old Southern money, solidifying his future in politics. The guy’s story was awesome, but he was a city slicker, and we were in the boonies. He was, without a doubt, a hard sell. He wasn’t a good old boy, he wasn’t a local, and he wasn’t down to earth. But he was a good guy and he wanted to win. He really fucking wanted to win.

When I was brought on the team, I had been poached away from another campaign a few states over, and was therefore arriving a little late in the game. Unsurprisingly, I was the only girl, meaning my title had gone from “Catie Warren, director of finance” to “Catie Warren, director of finance/secretary/maid/refiller of coffee/personal stylist/all-around office bitch.”

My first request when I arrived at the office on my first day was to see the campaign literature they had been mailing to constituents and passing out during events. And, to put it nicely, they were fucking terrible. As I flipped through them, it seemed like each one was somehow, someway worse than the last. One had Jack* (the candidate, whose name has been changed for obvious reasons) in an Armani suit, shaking hands with factory workers. Another had him relaxing on the porch of his multimillion dollar estate, his Luccheses in full view.

“We know they’re bad,” said the campaign manager, looking like just a shell of a man. “But he doesn’t like dressing down. Claims it makes him look like a poor.”

Great. Using the word “poor” as a noun — just a real man of the people.

After a few weeks of phone calls and parties and scamming people out of money, the time had finally come for new campaign pictures. This was it, this was my moment. I sat the campaign manager down and essentially said that while I, a semi-shitty person, enjoyed hearing off-color jokes about both race and socioeconomic status, it wasn’t really appropriate for Jack to continue looking like the kind of person who enjoyed telling them — even if he was that kind of person. So, we needed a change. Jack needed a complete wardrobe overhaul. No more designers. No more suits. No more lizard boots. He needed jeans. He needed Kirkland. He needed to lose the Rolex.

The day before the photos were taken, it was decided that because Jack had apparently no acceptable clothes in his own closet, he would need to go shopping. And because every other staffer was conveniently busy that day, the task fell on me. It was now my job to find my boss some “poor people” jeans.

When we met at the mall one town over, Jack was visibly distressed. He was kind of shaky and irritable and was just being an all-around dick, so I took it upon myself to apologize for the situation at hand. I understood that to a candidate, it probably seemed like shopping for jeans was a laughable waste of time, but it wasn’t. These were important jeans. Magic jeans, even. These were the jeans that would transform him from “Jack: the northern prick who has nothing in common with us other than the fact that this is where his wife’s great, great-grandfather decided to grow tobacco” to “Jack: the nice, normal guy who happens to go to Washington every few days.” So into the mall we went.

I started describing the jeans as we walked through the main entrance. Basically, I was looking for normal, everyday dad jeans. Wranglers. Levi’s. Maybe even some Lees. Nothing special. Just run-of-the-mill, no frills jeans.

But Jack had something else in mind.

As we walked into one of the nicer department stores, he made a beeline for the tight, grayish, embellished jeans made popular by the black and white Guess ads featuring Anna Nicole Smith and her army of pills/Eurotrash. His choice in jeans solidified my hunch that he was, in fact, the child of immigrant parents, and I immediately wondered if he had a pair of capris hidden somewhere in the back of his closet — but that question was for another day. This day was for jeans.

I mustered up the courage to tell this man old enough to be my father and rich enough to make me disappear that his taste in clothes was laughable at best and teetering on the edge of blatant homosexuality at worst (think of the targeted voters). I so badly wanted to ask him if the image he wanted his constituents to have of him was that of “sassy gay man” when he told me for the third time about how much he loved the form-fitting, acid washed pants he was now holding against himself, but I fought the urge. Instead, I simply just stated that they were not what I had in mind.

I suggested that he go grab a cup of coffee and let me look around. About twenty minutes later, Jack came back, coffee in hand, and found me standing by the dressing room holding a few pairs of acceptable pants. As he watched me lay the jeans down before him, he started groaning and scoffing and muttering curse words under his breath.

“I’m not dressing like a fucking farmer.”

I did a double take and looked back at the jeans — not overalls — laying on the table and just stared blankly at him in response. Without a word, I gathered the pants, picked them up, thrust them at his chest, and nodded toward the dressing room. Annoyed, he started walking into the dressing room and then turned back to just continue being difficult.

“Aren’t you coming in with me?”

I laughed. Then stared blankly. Then glared. Then said no. Then laughed again out of pure awkwardness.

“I didn’t mean IN the room with me. But, rather, by the door. How am I supposed to know if they look good?”

I continued staring blankly at him. After about thirteen seconds of just looking at each other, he turned and walked into the room. Alone.

With each pair of pants he tried on, he’d dramatically walk outside into the main area of the store, do a lap, and loudly complain about how much he hated those particular jeans. By the time he’d tried on the last pair, we had seven different sales people standing around us, offering opinions. Everyone told him he looked great. But he didn’t agree.

“I don’t look distinguished. I look like I make eight dollars an hour.”

…crickets.

As I put away the jeans that he refused to buy and apologized for the comments, I scanned the store and found Jack standing at a cash register, purchasing the gray Guess-like jeans. The next day, I stood by and watched Jack pose for pictures in front of a barn with his wife and kids, meet with constituents, and speak at a town hall event. He wore his new favorite bedazzled jeans in every single shot.

And as you might have guessed, we lost the election.

Catie struggles with adulthood and has been celebrating her 21st birthday for the past three years. She attended college in the nation’s capital and to this day is angry that Pit Bull lied to her, as you cannot, in fact, party on The White House lawn. Prior to her success with PGP, Catie was most famous for being featured in her hometown newspaper regarding her 5th grade Science Fair Project for which she did not place. In her spare time, she enjoys attributing famous historical quotes to Marilyn Monroe and getting in fights with thirteen year olds on twitter. Email: catie@grandex.co

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