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

  After explaining that the rest of America goes to about one movie a month, pays an average of $600 a month for a mortgage, and could make four car payments on the $1200 a month parking fee, I knew I had made an impact.

  My sister turned to me and said, “I suppose I could do without the hot dogs.”

  —Todd Lancaster

  * * *

  Ah, home sweet home. Fletch hauls my bags up the fifty steps to our apartment…the one drawback to living in the penthouse. You’d think my ass would be smaller from all the climbing.

  As I unpack, I shiver with delight over all the designer labels…Tomatsu, Karen Kane, Dana Buchman, Ralph Lauren, a few prized pieces of Chanel and Versace, etc. I really ought to thank Shelly Decker for my fabulous wardrobe. No, Shelly isn’t my personal shopper. She’s the hateful little troll who drew the thinly disguised comic strip about me (Muffy the Preppy, my ass) and abused her position as features editor to place it smack on page two of our high school newspaper. If it hadn’t been for her public goading, I’d never have become the fashionista I am today. Even almost eighteen years later, my blood boils about the day I saw that stupid cartoon….

  “Look at this,” I shrieked while throwing open the front door and tossing my book bag in the corner. “Look! LOOK! I have been wronged!”

  “S’matter with you, Peeg?” Todd asked from the couch in the family room off the kitchen. My brother had stationed himself there before I left for school hours earlier, apparently still recuperating from his freshman year of college. He’d indulged in a steady diet of ginger ale and Gomer Pyle reruns for the past three days. The nine months without him in the house had been heavenly, as his sole purpose in life was to make mine miserable. Normally I’d attack him for the “peeg” comment (really, how can you be a pig when you can squeeze into size five Jordache jeans?) but I had other priorities.

  “I’m not talking to you, TOAD. Mom, look at this…. It’s awful! I’m ruined! I have been personally attacked!” I wailed while wildly waving a copy of my high school newspaper.

  “Oh, Jen, I’m sure you’re overreacting again. Let me see.” Mom put down her load of clean laundry and perused the offered page, eyes scanning back and forth. She wrinkled her brow. “You’re ruined because the drama club chose Little Mary Sunshine for the fall play?”

  “No, it’s this right here!” I stabbed the offending section with a pointed finger.

  “The Muffy the Preppy comic strip?”

  “Yes! Read it!”

  “Muffy the Preppy says…hmm, hmm, hmm…real pearls from Hudsons…hmm, hmm…shut up, you animals…hmm, hmm…and I’m done. It’s cute. Did you draw this?”

  “MOTHER! How could you think it’s cute? That bitch Shelly Decker drew this about ME! See? She’s got the pearls and the Shet-land sweater tied around the shoulders and everything. And it’s the last day of school, and this insult is all anyone will think about the whole summer.”

  “I know you feel you’re an adult, but you may not swear in this house.” Over my mother’s shoulder, I could see Todd making faces and flipping me off. I’d deal with him later. “I think you’re being melodramatic. What’s the big deal?”

  “Do you not understand that I have a reputation to uphold in that school? I cannot just have my character assassinated by the media.”

  “Sorry, Zsa Zsa, I forgot that you were so averse to negative publicity.” My mother resumed folding the load of whites she’d been holding.

  “Mother! You’re not taking this seriously! Don’t mock me! I had to work really hard to fit in here after we moved from New Jersey. It took YEARS for me to work my way up to the semicool crowd, and I had to lose the atrocious Jersey accent to do it. The last thing I need is some asshole pointing out how I’m different from the rest of them. Don’t you realize that the animals separated from the herd die? DO YOU WANT ME TO DIE??”

  “WATCH THE MOUTH, missy. I understand you’re upset. What I don’t understand is why Shelly would draw a cartoon about you. She’s your best friend.”

  “Well, yes, she was, but not anymore.”

  “Since when?”

  “A while, OK?”

  Todd interjected, “Hey, Mom, better get Dad’s attorney on the phone to talk about suing the school paper for libel.”

  “MOM!”

  “Now you’re both being ridiculous. Todd, pipe down. What happened with Shelly?”

  “It was all her fault.”

  “Jennifer, what did you do?” Why did she always assume it was my fault?22

  “She was jealous.”

  “Of what?”

  “Nothing.”

  “I think there’s more to the story,” Todd volunteered helpfully from the other room.

  “Shut UP, Toad. OK, remember when you had to go back to Boston to help Grampa after his surgery? Well, I kind of wore your pearls while you were out of town.”

  “I do not recall giving you permission to wear them.”

  “I was allowed to because Dad saw them on me and didn’t say I couldn’t.”

  “Not an excuse. Your father is oblivious. He didn’t notice for three weeks when we painted the den. But why would my necklace upset Shelly?”

  “I might have mentioned they were real pearls. From Hudsons.”

  “So?”

  “About fifteen times.”

  My mother sighed deeply. “Where did we go wrong with you? You didn’t learn this behavior from me. When I was your age, I never had new clothes. All I had were the items my sisters handed down to me. The only reason I dressed as nicely as I did was because I taught myself to sew and—”

  “Is this where you tell us how you only had one pair of wool socks when you were a girl and you had to hand wash them every night?” I whined.23

  “I can’t believe she has any friends the way she acts,” my brother added. Why couldn’t I have been born an only child?

  “Shove it, frat boy. Mom, do you see the problem I have? Shelly just threw down the gauntlet, OK? She issued a challenge. If she’s going to label me in a public forum, then I have to be the preppiest preppy to ever walk the halls of my high school. Now that I’ve been singled out, I’m obligated to deliver. People are going to expect it. I didn’t start this feud, but I’ll be damned if I don’t finish it. So, I’m going to need a LOT of new stuff for back to school. Why don’t you get Dad’s credit card and we can start shopping now. You know, beat the rush and all.”

  “Ha! Good one, Jen.”

  “You’re not going to help me? Why? Because of your boring sock story?”

  “You get $100 for back-to-school clothes, and you know it, and that amount will decrease if you don’t watch it with the cusses. If you want more than I plan to pay for, then I suggest you get a job.”

  “How am I supposed to do that? I can’t drive yet, and there’s no place to work in this stupid subdivision.”

  “When I was your age, I made money for fabric by watching my sister’s children. This neighborhood is full of kids—why don’t you give babysitting a try?”

  “But I hate kids.”

  “Yet you love money.”

  “You make an excellent point.”

  Why had I never considered babysitting before? Our neighborhood was crawling with little kids…. It was a veritable gold mine! I quickly ran figures in my head—if I could earn fifty dollars a week for the next ten weeks of summer, then—holy cats!—I’d be the best-dressed girl in the whole TOWN. Visions of pink oxford cloth and tartan plaid danced in my head. With five hundred dollars, I’d get tassel AND penny loafers, puffy velvet headbands, whale-print mini-skirts, and a Bermuda bag to match every outfit!

  “Do you think if I typed up a flyer Dad’s secretary could make copies? That way I could pass them out to neighbors.”

  “I’m sure she would if you asked nicely.”

  “I’m going to work on it now!” I grabbed my book bag and headed for the stairs. Remembering something I’d left undone, I returned to the kitchen. “I forgot to tell you guys…hey, T
oad?” I pulled an envelope from my bag and handed it to my mother. “Your grades came today!” I dashed to my room as the blood drained from my brother’s face.

  That’s how in the summer of 1983 I became known as Babysitter Über Alles. I was in demand, but not because of my tremendous prowess with children. I’ve never been great with kids—they are self-centered, attention-grabbing, illogical, sticky little beasts with terrible taste in TV shows.24

  I was nice to my charges for the most part, but any maternal stirrings I might have had were squelched by their shrill voices and garbled English, which I found annoying, not endearing. Don’t get me started on their rambling stories and barrages of precocious questions. “Jen, why do the birds sing? Jen, why does the grass grow? Jen, how do sharks sleep? Jen, why is the sky blue?” The sky is blue because God hates you, OK? Worst of all, kids always seemed to think it was all about them.

  And everyone knows it’s really all about me.

  The sole reason I was popular was because I tackled housework without being asked. My clients knew that upon their return, they’d find gleaming appliances, empty sinks, and pristine carpets. I quickly learned that elbow grease equaled more penny loafers and oxford cloth shirts, and the more I had, the more Shelly would turn pink and green with envy. Heh.

  Much as children annoyed me, dealing with them was a necessary evil. Once one young insurgent, Daniel Bedlamski, wouldn’t get out of the pool, forcing me to enact Jen’s Babysitting Axiom #95: First Ask Nicely and Precisely. I crafted these rules of engagement to better deal with Danny, as arguing with him instead of scrubbing had cost me more than one tip.

  Prior to his refusal, I’d been perusing for the umpteenth time my new personal bible and style guide, The Official Preppy Handbook. I flipped through it while keeping one eye on Danny, as I figured his drowning might negatively affect my compensation. But then he wouldn’t get out of the pool, so I closed the book and headed toward the water.

  I swiftly removed my Bass Weejuns and argyle socks. I cuffed my khaki walking shorts, climbed down the first two steps in the shallow end, and met Danny’s gaze. I smiled and adjusted my strand of pearls.25 He splashed a bit and grinned back at me, his white-blond hair slick with water, cheeks pink and freckled, and cerulean blue eyes dancing. Jen’s Babysitting Axiom #37: The More Angelic They Look, the More Evil They Are. With Danny’s cherubic features, he was the devil incarnate.

  Sweetly, I said, “Danny, honey, I asked you to please get out of the pool.” I’d taken to calling the kids endearing pet names instead of swearing since I’d been fired for calling Markie Everhart a “fucktard.”26

  Danny shook his head wildly and droplets of water made patterns on my linen shorts. He squealed and shrieked while I smiled more widely through gritted teeth. (Jen’s Babysitting Axiom #421: Assume a Healthy Glow, Agitation Never Show.) I flipped up the collars on my layered polo shirts and tilted my head in the trademark flirty manner Britney Spears would eventually steal from me.

  I said, “I bet you’re having so much fun right now that you don’t want to stop.” He laughed and splashed some more, this time speckling the natty tortoiseshell Ray•Bans that I’d swiped off Todd’s dresser earlier that day.

  I glanced at my cheap Timex fitted with a grosgrain watchband. I needed to get that brat out of the pool tout de suite if I was going to tackle the sink full of dishes. I was counting on Mrs. Bedlamski’s tip. The club pro at the local golf course was holding a particular Izod for me, but only until the end of the afternoon.

  And this was no ordinary polo. It was bubble gum pink and Kelly green striped, and instead of a boring old knit collar, this one was constructed of crisp and immaculate white cotton. This shirt spoke of prep schools and old money and summers on the Vineyard and the kind of old-boy networks that don’t exist on the plains of northeast Indiana. I knew the minute I put that shirt on, I’d immediately be catapulted away from my painfully average Midwestern roots. To this day it is singularly the greatest shirt I’ve ever seen in my life. Also? I knew that Shelly Decker would shit itty-bitty alligators the minute she saw it on me.

  “Danny, sweetie”—really meaning fucktard—“I have to go in the house and you can’t swim alone. You need to get out of the pool right this second.” He giggled and screeched and ducked his head under water. This time his splashing hit my book.

  OH. NO. HE. DIDN’T.

  When he came up for air, I brushed the pageboy out of my eyes and retied my tartan hair bow, careful to do something with my hands to keep them from making choking motions around the hell spawn’s neck. It was time to break out the big guns…Jen’s Babysitting Axiom #578: Don’t Get Mad, Get Medieval.

  I leaned in close and whispered, “Danny boy, you are coming out right now. Or else I’m going to take that radio from the table, throw it in this pool, and electrocute you.”

  Tell me that little bastard didn’t fly out of the water.

  Harsh? Perhaps. But I finished the dishes, got the extra tip, bought the shirt, and wore it on my first day of eleventh grade. Shelly was beside herself when she saw me. In a deliciously ironic twist, my best friend, Carol, had been named editor in chief and she appointed me to be the new features editor. My first order of business? Scrapping the Muffy strip, of course.

  As for Danny, he’s all grown-up now. But I have to wonder if any time he sees madras plaid, he doesn’t die just a tiny bit inside.

  You know, the corporate world really isn’t that different from babysitting. It’s all a matter of understanding when to kick off your loafers and take charge.27 Plus, most of the people I work with act like children, so the transition to the professional world was practically seamless. No wonder I rock it so hard.

  However, I will concede that working for a nice company makes things a lot easier. I am so much happier at Corp. Com. than I ever was at my last job at Midwest IR. The work environment is really positive and the pressure is way less intense, even though I have to put up with Will’s antics. What a colossal washout he is. Although I report to the head of my product line in New York, I had to interview with Will because he runs Chicago. And what do you think his selling point was in my interview? Room for advancement? Stock options? A generous 401(k) match? No. Will loved Corp. Com. because they gave employees free sodas. Yes, and so does McDonald’s but you don’t see people lining up to work there.

  My problem with Will began on day one of my employment. I arrived sporting a smashing tweed Tahari suit trimmed in striking black fringe, ready to get down to business.

  “Hi, Jen Lancaster, pleasure to see you again,” I said, extending my hand.

  “Yeah, um, hey, Jenny, I, uh,” he started.

  “It’s Jen,” I interrupt.28

  “What? Oh, yeah. Sorry. Um, yeah. So, um, welcome. Yeah. You want a soda or something? They’re free!” he reminded me.

  “Thanks, no. I’d just like to get started. I’ve got a lot of ideas to flesh out, so if you’ll be so kind to show me the way to my office, I can do just that.”

  Will nervously looked around, pulling his collar open with one finger. “Um, yeah. There’s a slight problem. I, um, kind of turned your office into a storage room.”

  “What?” No. No, no, no! Part of the reason I agreed to join the organization was because they promised me my own office. I was NOT about to rejoin the land of the cubicle dwellers.

  “Yeah, I accidentally ordered too much marketing material and I needed a place to keep it and corporate won’t let me send it back. So, um, yeah, sorry ’bout that.”

  “OK.” I wasn’t thrilled, but they were still paying me an outrageous sum, so I guessed I could make do. “Where will I be sitting?”

  “Um, we don’t have a receptionist anymore, so her desk is open. Would that be cool? It’s, like, a really big work space.”

  I glanced at the desk. “Don’t people enter through these doors, and won’t they naturally come to me—the person sitting at the reception desk—for assistance?”

  “Um, well, not that much
, and you could page people if they had a visitor and delivering stuff won’t take you too long and—”

  I interrupted again. “Will, would distributing UPS packages really be what you consider the best use of my time and salary?”

  “Um, um…” he stammered.

  “No? Then get me a different work space.”

  “OK, follow me.” He took off down a long hallway as I trailed behind him a few paces.

  “And, seriously? Consider Ritalin. They’re doing amazing things with adult ADD lately.”

  “What’d you say?” Will turned with an accusatory look on his face.

  “I said I was seriously G-L-A-D to be on board. Now let’s find me that desk.”

  So I’m back in a cube again. It’s not as bad as I thought since it’s relatively private and I’ve got a great lake view. Still, there’s nothing more satisfying than righteously slamming your office door when the hoi polloi gets too loud. Speaking of loud, the salesmen at Midwest IR were incredibly noisy. Someone thought our team would produce more if we had a creative outlet. Were we supplied with piped-in music or theater tickets or thought-provoking team-building exercises? No. We got an air hockey table. I can’t tell you how annoyed I was by the testosterone-charged cheers that ricocheted off the walls all day. Most days I’d swear I worked in a sports bar.

  My old coworkers used to bitch when I’d scoot out of the office after eight hours. They didn’t understand how I managed to meet my goals, especially since they claimed to work twelve-hour days. Yeah, you know what, guys? I actually have worked twelve-hour days. Those four hours you played air hockey? Don’t count.

  I suspected my old job would be a challenge because it was an investor relations firm and I knew nothing about the financial world. I thought PE ratios had to do with gym class statistics and mutual funds were the bills in Fletch’s wallet.

  Stan, Midwest IR’s chief operating officer, promised to teach me everything I needed to know about the business. I jumped at the chance to learn from him. He may have been clad in a $1200 suit and Ferragamo loafers, but he was still “straight outta Jersey.” I was enamored by his Newark-tinged plain talk. Such a refreshing change from the mild-mannered, mealymouthed Midwesterners at the HMO! Sure, my old bosses were pleasant and polite, but they tried to steal credit for my deals and ideas more times than I care to mention.