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Oprah Made Me Quit My Job...and nipples.


In 2005 Oprah ruined my life. That’s entirely an overstatement but she did change it significantly. Usually Oprah is attributed with making people’s lives easier. She’ll give them a new car, 17 iPads, a small country in the southern hemisphere. All Oprah ever gave me was a hard time.

In May of 2005 I was working at the Jockey outlet store at the Tanger Mall in Blowing Rock, North Carolina. Selling discounted underwear was by no means a glamorous job, but it was easy, it paid relatively well, and I worked with some good people. We felt united in the necessary but frequently awkward role we played as underwear retailers. I always felt like I was doing a service because I knew that buying underwear made some people feel vulnerable. I myself have gone to a store to buy underwear and then when I realized who would be ringing me up, I put it back and left the store. Either they were too male, or too attractive, or too all of the above. I hated the idea of some size 0 asshole (whose panties could fit a newborn…or an Olson twin) or some dude holding up the parachute that I just purchased to cover my not-so-modest butt. (If only my butt were as modest as my income). I was sensitive to the fact that many of my customers were uncomfortable with me seeing the things that they were going to put on their privates. I tried to ring up uncomfortable customers as quickly and discreetly as possible.

I was getting used to my job and the awkwardness that came along with it. I had survived selling a former high school teacher visiting the mountains for the weekend his tighty whities. (We both pretended not to recognize each other). I kept a straight face while one of my professors bought almost $100 dollars worth of thongs. I didn’t barf when someone returned obviously USED and UNWASHED merchandise (which was sadly not prohibited from the Jockey return policy ). These were awkward—and at times, disgusting—situations that I could handle. In May of 2005 though, Oprah changed the game for me completely. She flooded our store with uncomfortable…and I’ve never been a very good swimmer. Oprah did a show called “The Bra Revolution” where she told the world that 85% of women wear the wrong sized bra. I know that there is some truth to this based on the exorbitant number of 36Bs we sold on a daily basis, but this was never considered a problem until Oprah said it was. She aired her Bra Intervention show with impressive before and after shots and women cried and thanked Oprah for changing their lives. I didn’t actually see the show, but I did have the misfortune of working at Jockey the day after. And when Oprah told the women of America that they needed to get a bra fitting, they listened. All of them.

Before we could open the store the day after the show, a few women had congregated outside in the cool mountain air, peering in the windows. When we opened the doors a few minutes later, the women were gushing (in more ways than one, thanks to their ill-fitting bras that they were suddenly cognizant of).

“We’re here to get a bra fitting,” they said practically in unison.

The girl I was opening with apologized to the women and told them that only our manager knew how to give bra fittings and she was on vacation.

The women reacted as if my co-worker had just informed them that she was a cannibal who enjoyed the meat of younger children because it was exceptionally tender.

The booby-mob left disappointed that they weren’t entitled to a complimentary bra fitting at the outlet mall where they bought their underwear at a discounted price. But by lunchtime, at least 15 women had come into the store for the same reason. And they all left pissed because Oprah had given them a mission and we just kept derailing it.

Apparently Jockey stores all over the country had the same experience. Oprah was just trying to lead her people to the Promised Land; a land of milk (no pun intended) and honey where back fat wasn’t an issue, and bras never tried to crawl up a person’s shoulder blades. And we were ill-equipped. There was a Bra Revolution going on, and Jockey was going to have to change with the times or get left in the dust. By the end of the week, I found myself in the manager’s office watching a hokey video about how to successfully complete a bra fitting. I had to take and pass 8 quizzes that were sent straight to corporate that proved I knew what I was doing. We replaced our window signs that advertised panty-line free briefs with signs that announced how ready and excited we were measure you for a bra, and you for a bra…everybody gets a bra!!!!

This is where my job went from being kind of uncomfortable to so uncomfortable that I couldn’t hardly stand it. I started to dread work, because I knew there was a good chance I would have to follow some shirtless stranger into a dressing room and feel her up. Since I have the sense of humor and emotional maturity of a 15 year old boy, I struggle with boobs. I find cleavage to be generally unsettling, and if I’m around it, I really struggle to avert my eyes. Call it breast-envy, but I just can’t stop staring at cleavage when it’s there. Many of these women were originally too shy to request a bra-fitting, but the power of Oprah compelled them. The big O gave them the resolve they were lacking. Plus, they expected this new bra to completely change their lives. Many of the women seemed really disappointed when they found the right bra for them…and it didn’t pay off their mortgage, teach them a 2nd language, or find homes for every homeless animal.

After a few weeks of bra-fitting insanity, I grew accustomed to the new and revealing aspects of my job. I even got kind of good at averting my eyes. (Okay, so I cheated. I took advantage of my nearsightedness and just took my glasses off). I approached it with the same self-righteous sense of purpose as I did the rest of the job. I was acclimated and I started to forgive Oprah for the strange butterfly effect she had detonated. That was until the day that an elderly woman came into the store. Actually, she was probably elderly when Nixon was president, so by 2005 she was a relic. This sweet, ancient lady wanted a bra fitting. I helped her to the dressing room, told her to take off her shirt, but leave on her bra and I would come in to fit her in just a minute.

Nothing could have prepared me for the next 3 minutes of my life. Nothing. I knocked on the dressing room door and slipped in only to find a completely naked from the waist up 170 year old woman. I apologized, and slipped back out into the store reminding her that she needed to leave her bra on.

“Honey I don’t have a bra. That’s why I’m buying one.”

Great. Just great.

I took a deep breath, stepped back in and completed a bra fitting that would become infamous. I tried so hard to keep it together and avert my eyes, but our dressing room had multiple mirrors that allowed you to see yourself from different angles. Everywhere I looked and didn't look there were nipples…that had migrated south for the winter.

Fortunately the woman was comfortable enough for the both of us and we made it through the bra fitting. I rang her up and even convinced her to sign up for a Jockey club card. She wore the bra out and I did feel good after providing a service for someone who needed it. But I also realized I could never again say "never have I ever felt up a bare-chested old lady." I decided I had peaked as a bra-fitting specialist; I turned in my notice later that week. I looked for a job that didn’t involve moisture wicking fabrics or seeing people in their skivvies.

So thanks Oprah. If it weren’t for you, I never would have made it to 2nd base with that sweet old lady.

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