Bitter is the New Black : Confessions of a Condescending, Egomaniacal, Self-Centered Smartass,Or, Why You Should Never Carry A Prada Bag to the Unemployment Office

by Jen Lancaster

  P.S. I have recently started a management company to manage my portfolio of commercial real estate properties. We are looking for several in-house maintenance people. Feel free to forward your resume, or we can fax you an application. GED or equivalent required.

  * * *

  “Are you going to dignify this with a response?” Fletch asks. We’re in the den, and Fletch is standing over my shoulder, rereading Calvin’s e-mail.

  “Maybe. When I read this the first time, I thought it was funny. Nothing like a little ribbing between old friends, you know? But then I reread it, realized he was actually being mean, and got mad.”

  “Regardless of shared history, no one has the right to talk to you like that. If you reply, what are you going to say?”

  “I’m thinking about it now. When I come up with a response, I’ll run it past you.” He heads out to walk the dogs.

  I grab a Diet Dr Pepper and a tumbler of ice and settle in front of the computer to craft a snappy retort. As I try to string together the perfect response, I begin to reminisce.

  Calvin was in the same fraternity as my brother. I haven’t seen or talked to Cal since he was a groomsman in my brother’s wedding almost ten years ago. Cal and Todd’s other fraternity brothers behaved rather inappropriately during the ceremony. Fortunately, they were so drunk none of them made it to the reception.

  Todd’s wedding was important because it marked a turning point in my “relationship” with Calvin and the rest of that crew. You see, when I arrived at college, I was a naive young girl, and I was impressed by, well, almost everything. I desperately wanted to leave my bourgeois roots behind me.

  When I met Calvin and the rest of his clique, I was blown away by how smart and witty and worldly they were.192 They’d all grown up in wealthy towns like Newport and Greenwich and Alexandria…. Certainly no one had spent his teens in an Indiana farming community like me! And they’d all done things I’d previously only read about in The Preppy Handbook…attended prep schools, summered on various Capes, captained yachts. As for me, I spent summers straining leaves out of my parents’ pool. Granted, there are worse fates than having an in-ground pool and needing to clean it, but I didn’t know it at the time.

  At that point in my life, I’d never met anyone who could slam a Little Kings beer AND quote Arthur Miller AND had a wardrobe full of Alexander Julian shirts. Naturally, I was enamored of Cal, as he represented everything that my seventeen-year-old mind considered “cool.” But I didn’t want to date him because at the time it didn’t occur to me that I could even be worthy of his affection. (Ironic, because I was 125 pounds at the time and had done the local beauty pageant circuit in high school.) Instead, I foisted my adorable roommate, Joanna, on him and lived vicariously through their chaste flirting.

  What I so desperately craved from him was his acceptance. He’d always been grudgingly nice to me out of respect for my brother and because he’d been raised well. Take these factors away, and I probably would not have even existed in his world. Yet I so wanted to be liked on my own merits. I tried everything within my power to gain his respect but didn’t realize that the role I played was that of a door-mat, thus ensuring we’d never be equals. For example, in return for being allowed to hang out in his room in the fraternity house, I would voluntarily run errands and do chores. “Need a button sewn on your shirt? Let me handle it!” “Want cute freshman girls at your next party? I’ll round them up for you!”

  My indentured servitude didn’t last long. The more I made my own friends, the more I took back the power that I’d so freely given away. Don’t get me wrong, I was still in awe of him. But I’d gained the tools to better mask it.193 Anyway, Cal eventually graduated, and I didn’t see him again until my brother’s wedding, although I’d occasionally hear an update about his so-called fabulous life.

  So, when Cal and the rest of his cohorts acted like drunken buffoons at Todd’s wedding—IN THEIR THIRTIES—the scales fell from my eyes, and I questioned why on earth I’d ever worshipped him.

  I mean, really, on what planet is a cute and eager-to-please seventeen-year-old girl considered a liability?

  I believe the last words I spoke to Cal before I received his e-mail were “Calvin, would you please shut the fuck up so we can finish taking these pictures?”

  The seventeen-year-old Jen would have been crushed if she’d received a condescending note from Cal the Magnificent, even if it was just meant to tease her.

  But what about the thirty-five-year-old Jen? The one with the big butt? Who lives in the ’hood and has a pit bull and actually LIKES polo shirts from Target? Who doesn’t have a job and is married to a regular guy from Indiana?

  She just laughed and laughed.

  * * *

  To: Cal Canter

  From: jen@jenlancaster.com

  Date: September 14, 2003

  Subject: Re: Little Blaster

  Hi Cal,

  I saw your name as the return address and assumed that my brother was playing some sort of trick on me. But as I read, I realized that Todd doesn’t have the skills needed to fake your level of arrogance and that this email was indeed the real thing.

  Aren’t I a lucky girl?

  I remain aware of your existence as Todd still starts the occasional sentence with the phrase “Calvin says…” You’ll be pleased—although probably not surprised—to know that this phrase precedes his lectures on things I’m doing wrong in my life, so I hear your name a lot.

  Thank you for your sage guidance on my job search. Sadly, I can’t get a fast food job because I’m not bilingual, necessary in my West Si-ee-de neighborhood. We also own a pit bull, so I DO meet all the qualifications to begin rollin’ with the Latin Kings. However, I’m keeping my gang-joining options open for now as a gal needs to choose her homies carefully, you know.

  I have to disagree with you on a couple of points on my potential writing career. As for financial gain, I currently make NO money, so any money earned would be considered a success. And I can’t see that anyone could find dirt or embarrassing stories about me that I wouldn’t first exploit myself, case in point, my Big Lebowski Night story on the web site. In it, I detail losing my shirt and vomiting on my neighbors.

  Hey, doesn’t it seem like just yesterday I was shouting at you to “shut the fuck up” at Todd’s wedding?

  By the way, have you completely morphed into Judge Smails from Caddyshack yet? You were well on your way the last time I saw you. Hope all is well at Bushwood.

  Fecklessly yours,

  Jen (Todd’s sister)

  * * *

  I’m outside pouring water on the newly laid sod in front of my building. As I finish dumping my eighty-sixth bucketful on the fledgling lawn to make sure the roots take hold, I realize I’m being watched. I look up to see two shadowy figures, although I can’t discern who they are because I’m temporarily blinded by the setting sun and the sweat pouring into my eyes. Then one of the figures barks, “HEY, JEN!” and I jump about four feet in the air, sending my bucket flying.

  There’s only one person I know who speaks with the kind of volume that makes people mentally construct storm shutters and tape up windows. “Joel! Fletch says you’ve been away for National Guard training. Did you just get back? And, Irene, how are you? What are you guys doing here? We haven’t seen you guys for ages! Please come in!”

  After hugs and a few more cheerful exclamations from all parties, I give them the tour. Fletch is equally delighted, and we gather on our deck. I’m so pleased to see them that I don’t realize I’m clad in cutoff sweatpants and a ratty T-shirt until I notice the odd looks I’m getting from the child millionaires next door.

  Before Joel arrived and I tossed my bucket, I caught a glimpse of the millionaires hosting their first dinner party alfresco. Their table was covered with an expensive spray of lilies so fragrant that I could smell them from our deck ten feet away. On their immaculately set Bloomingdale’s for the Home outdoor dining suite, pricey red wine twinkled in their
giant crystal goblets. Their purebred cocker spaniel sat patiently at their feet, confident in the knowledge that a delectable scrap of proscuitto had her name on it. And I’m pretty sure I noticed sorbet being served in frozen objets d’art between the pasta and grilled rainbow trout courses.

  Their guests fit the scene perfectly, too. The women had glossy, swinging bobbed coiffures and Just the Right Amount of makeup, dressed like an Ann Taylor catalog brought to life, their small, tasteful gold-hoop earrings and blindingly large engagement rings flashed in the late-afternoon sun. The men were hale and hearty in their Brooks Brothers casual wear and Rockports. They tittered about their healthy portfolios while lame jazz lightly wafted through the air on the outdoor speakers. Small lanterns and little candles provided a warming glow while the sun set.

  The scene is truly breathtaking.

  Until we come outside to mess it all up.

  Honestly, I try to keep Joel’s voice a decibel or two below ear-splitting, but to no avail. Joel cannot be contained. That’s why we went onto the deck in the first place. Had Joel been inside our house, the hippies downstairs would have blasted their Sgt. Pepper album over and over.194 The evening continues and Joel’s topics of conversation grow louder and more inappropriate.

  “THE CALIBER OF STRIPPERS IN TIJUANA ARE…”

  “YOU CAN FASHION ALMOST ANYTHING INTO A WEAPON. SPRAY STARCH CAN BE DEADLY WHEN YOU…”

  “SINCE MOST FIREFIGHTS TAKE PLACE IN AN AREA OF LESS THAN FOUR HUNDRED YARDS, I FIND THE ASSAULT RIFLE…”

  The glances from the other side of the fence are coming fast and furious now, and through narrowed eyes, they survey our soiree. “Wait a minute. Do they have a PIT BULL? That spastic dog is gnawing on the big black wolf-looking mutt and they’re both demanding sips of beer! And what IS that girl thinking, wearing sweaty gardening clothes and a ponytail to entertain? Are they drinking beer? That isn’t IMPORTED? Oh, my God, they’re drinking directly from the bottle! Don’t those savages own any pilsner glasses, for Christ’s sake? How come the fat one is sitting on the AC unit? Why don’t they just BUY more chairs if they don’t have proper seating? And what is the loud psychopath shouting about now? Gah! How much longer until THOSE PEOPLE leave this neighborhood and we can have some peace?”

  I guess it’s official now. We’re the white trash neighbors.

  Why am I oddly delighted by this fact?

  * * *

  To: jen@jenlancaster.com

  From: NYHS Publisher

  Date: September 16, 2003

  Subject: Rat Pack

  Jen,

  I ran across the Do We Need a New Ratpack? rant you posted on Craig’s List and I went crazy for it. Everyone here read it and they peed their pants. With your permission, I’d like to reprint it in the new magazine I’m starting. Please contact me at the address or number below.

  Thanks,

  Loren

  * * *

  * * *

  To: jen@jenlancaster.com

  From: Kate, DeFiore Literary Agency

  Date: September 18, 2003

  Subject: Craig’s List Postings

  Hi, Jen,

  I saw your To Every Company essay on Craig’s List and I followed the link to your website, which I then perused for an hour or so. You have a strong voice and a great way with words.

  I think you have a story to tell, and, as a literary agent, I may be able to help.

  If you’re interested, I’ve included my contact information.

  All the best,

  Kate

  * * *

  “Hello?”

  “Hi, this is Joe Thompson. May I speak with Jennifer Lancaster, please?”

  Joe Thompson?

  How do I know that name?

  “This is Jen speaking.”

  “Jen, hey, how are you?”

  “Fine, thanks. How are you?” And who are you?

  “Doing well, thanks for asking. Listen, Jen, we haven’t spoken in a while, but hung on to your résumé because I liked your moxie.” Oh, my God—this is the guy from THE MOTHER SHIP! I called him once a month for an entire year. I only stopped phoning him when he told me that he’d call me when he had something. I assumed that was his polite way of telling me to piss off.

  “Jen, I have the perfect position for you in our municipal bonds publishing division. I want to get you in here as soon as possible for a round of interviews.” He lowers his voice in a conspiratorial tone. “I shouldn’t be telling you this, but your reputation precedes you and you’re my first choice. Provided your interviews go well and your references check out, this job is likely yours.”

  The Mother Ship is finally CALLING ME HOME!!

  “Yes, I’m really happy for you, but I thought you decided to try making a living as a writer,” Fletch says. “Given the interest you’ve garnered lately, I’m surprised you’d even consider this. What do you know about municipal bonds?”

  “Well, nothing, actually, but the job wouldn’t be selling bonds—it would be selling a publication about bonds.” Which would be cool…right?

  “Let me rephrase the question: What do you know about selling bond publications? Wouldn’t you have to deal with all the financial people you used to hate?”

  “No, no, I hated the stupid PR girls. The financial people were OK.”

  “Really? Is that why you’re always going out for drinks with Ben? And exchanging pithy e-mails with the Joshes? And having your nails done with Lawrence?”

  My skin crawls just a bit. “I kind of forgot about them.”

  “I’m all for you bringing home a paycheck, but if you have a job you hate, you won’t be happy. You’ll try to compensate by overindulging, and that’s ultimately how we got in trouble in the first place.”

  I roll my eyes. “Do you think I’ve learned nothing in the past couple of years?”

  “I’m just saying you should weigh your options.”

  “I will, I will. Oh, can you give me a lift that day?” Fletch is already doing so well at his new job that we were able to buy a car. Granted, it’s a preowned Ford Taurus and our loan rate is one percentage point shy of usury, but it beats the hell out of the Ashland Avenue bus.

  “What time?” Fletch pulls up his schedule on his PDA.

  “Does twelve thirty work?”

  “Can do.”

  “Cool. I’m going to go do some research on the municipal bond market now. Maybe it’s more interesting than it sounds.” I give Fletch a kiss and go to the den.

  There is NOTHING interesting about the municipal bond market.

  I’m clad in one of my old power suits and I look fantastic.195 My shoes have been spit shined, courtesy of Fletch, and I’m still a lovely light brown from my summer bout with tanorexia.

  “I’m going to grab the mail. I’ll meet you outside by the car,” Fletch calls up the stairs.

  “OK, see you in a minute.” I slick a coat of Bloom’s Dolci gloss196 across my lips and I’m ready to go.

  I lock up and try to ignore the sad doggie faces watching me from the window. I can’t even look at them. If I feel this guilty leaving them for a couple of hours, what’s it going to be like when I have to go to work every day and they’re all alone?

  When I get to the car, I notice a package on my seat.

  “What’s this?” I ask.

  “It came for you in the mail.”

  “Really?” I tear it open and a variety of presents spill into my lap. I examine all sorts of treats, such as pretty nail polishes, a mixed CD, and bags of my favorite candy. “This is lovely!” I dig through the box searching for a note.

  * * *

  Jen,

  I wanted to send you a token of my appreciation. I know it seems weird to send you presents, especially seeing how we’ve never met, but your advice has been invaluable to me. It’s because of your input that I didn’t dump my boyfriend…or should I say my FIANCEE!

  Although I wish you the best of luck with your interview, the selfish part of me hopes you’ll decide
to keep writing instead. Whatever you choose, thanks for inspiring me on a daily basis!

  Kelly in Canada

  * * *

  Fletch glances at my lap as he navigates the car out of the alley. “Who’s it from?”

  Lost in thought, I finally reply, “A fan.”

  The interviews go tremendously well, and as a company, the Mother Ship is everything I ever dreamed it would be. They make me a generous offer and I should be turning cartwheels. And yet, I’m just not sure. They gave me until Monday to make a decision, which is good because I have no idea what to do right now.

  On the one hand, this job is almost everything I’ve ever wanted in an employment situation. The benefits are great, there’s a tremendous opportunity for growth, and the money is spectacular. On the other, what if I actually have the chance to start a career as a writer? The literary agency wants to me to sign with them. Although being under contract is no guarantee of success, it’s definitely a leg up. My mother asked why I couldn’t take the job and write, but that’s not how I operate. I can only do one thing at a time, and with what I need to learn about the bond market, I can’t see doing both.

  Fletch has been no guidepost whatsoever. He keeps telling me to do what I think is best, and he’ll support whatever decision I make. What kind of bullshit is that?

  I’m all stressed out and the fact that I just started Atkins isn’t helping. I bet I could make sense of everything if I could just think about it over a plate of jelly donuts. While I’m busy crafting a decision matrix on a spreadsheet, my phone rings. “Hello?”