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Celebrities, Courvoisier, and Costumes


I have some things to tell you about celebrities and working in bars and sleeping with married men. Listen up.

Dear You,

When you are 19 and (illegally) working at your first ever alcohol-related job, a day will come when you are suddenly faced with the expectation that you make a piña colada for Jada Pinkett. Relax. Yes, this will be unnerving, obviously. I mean, you barely know anything about rum-based drinks yet. And you have only ever used a blender maybe once in your life up to now - when you tried to jazz up those Slim-Fasts with extra ice and banana - remember that? Anyway, you’ll be working there by yourself, at your first bartending job, on a high floor of the Sheraton Hotel in Dallas.

You’re staying with your sister, who is showing you the ropes of a viable starter career. You came to Dallas, a place that you don’t really like, because all your friends from college went home for the summer and because you think it’ll be more fun there than telling the customers at Crabtree and Evelyn about the difference between a rose’s scent in the morning and at night. And because you have wanted to get a tattoo ever since you saw Drew Barrymore’s and figure they’ll be cheaper in Dallas than Chicago (good call). Of course, the hotel will happily hire you, dum dum that you are, because nobody with any sense would ever want this job.

I know what you are thinking. You are thinking a job at a pool bar making blended drinks for Jada Pinkett sounds awesome! You are thinking that the money would be great (more ankle bracelets!) and the atmosphere would be glamorous (rich Texans and celebs!) and that you would love to spend a summer by the pool (tan!tan!tan!) while getting paid. And while yes, Jada is kind and gorgeous and smells like Valentine’s Day, she is not your typical Dallas Sheraton Hotel Pool Bar customer. I must tell you - you will not make very much money here, and there is nothing inherently glamorous about serving people drinks with way too much sugar in them.

It may surprise you to know that Jada Pinkett and Wesley Snipes (not as kind) will be your only customers that day, because - bad news - no one really patronizes the pool bar. Because no one really comes to the pool. See, this is a real corporate-y hotel, which is to say that the kind of people who usually stay there in any given summer are nothing like a Pinkett or a Snipes.


No, this indistinguishable lot have not just come from a film set and don’t smell anything like Valentine’s Day. They have had to schlep, mid-week and invariably with a quick turnaround, from some regional airport to the sweltering heat of DFW to satisfy the requirements of their non-dream job. They will spend their plane ride obsessively futzing with a Power Point presentation or an Excel spreadsheet, trying to ride that line of mini-Jack Daniels drunkenness, hoping to get high enough to endure this tedium without jumping out the window, but not so sloshed that they fall asleep with their mouths wide open and drool on their one good suit. These folks - these average hotel guests - in their beat up wing-tips and non-breathable blouses, would much rather binge on mini-fridge chocolate and pay-per-view porn than sit by or in the too cold pool, with its sweeping views of several other nondescript office buildings.

But don’t get me wrong! You should still do it! It’ll be fun. You will learn to make those fruity drinks. You will love hitting the post-work Whataburger drive thru with your sister at 3am. You will make friends who will take you out on the town, and one night you will make out with a hot guy named Dylan who drives a Camaro and buys you too many Cosmopolitans at a very cheesy club. At this club, you will dance to music you don’t like and talk about things that don’t interest you, but you will have so much fun anyway. You are trying on this persona, this Dallas girl persona, to see if it fits. You get the idea that maybe life is just better as a Mary Kay- wearing, Jesus- loving, big haired, stewardess type. Maybe blondes do have more fun!

But then Jerry Garcia will die and you will call your best friend at home. You and she will cry together as you listen to We Bid You Goodnight on your cassette tape copy of the 1970 Fillmore East show. You will try to reconcile the part of you that loves the Grateful Dead with the part of you that craves a glamorous world in which everyone generally wears shoes. And you will wring your hands about what kind of tattoo you should get or whether you should call Dylan again and you will feel torn about both choices. You will worry about the pain from both of those things but neither will really hurt, and by the time you go back to Chicago you will decide you are much more Janis Joplin than Jessica Simpson.

Then, in 1997, when you are 21, and you’ve worked food and beverage service long enough to know that legit bars don’t serve piña coladas, you will opt to work for real money at a late night Chicago blues club called Kingston Mines. This job will be a lifesaver for you because the money is truly fantastic - up to $400/night (!) - and for this reason, you will not complain about coming into work at 7pm smelling of shampoo and Ripened Raspberry Body Spray and going home at 5am smelling like Marlboro Lights and Heineken. You will love the gritty charm of this place, even though the physical task is to carry a full tray of pints of beer (10 lbs.!) through a crowd of “dancers” who will routinely knock your tray of drinks down your shirt and/or step on your feet with sharp heels.

It’s ok. You will learn to wear clogs, which, on you - you young thing- will look adorable and not yet old lady-ish. You will figure out that you need to carry a bar towel on you at all times, and you will get increasingly more comfortable verbally establishing your boundaries to people over dangerously high decibel-levels. Hearing loss is, I’m sorry, inevitable.

You will also learn that Mick Jagger has someone call the club before his arrival, does not dare come in through the front door, rolls with an entourage of 10-15 people, wears sunglasses in the dark, and DOES NOT order his own drinks. Yes, you will be disappointed when his assistant only tips you the regular amount but that’s ok, because in just a few months, you will share a brief and meaningful exchange at a nearby table with someone who tips you terrifically, and who will solemnly buy you a snifter of Courvoisier to drink with him because, sadly, Princess Diana has finally been consumed by the tabloid media, and it has taken you both quite by surprise.

It is a wild juxtaposition - this somber event and the sloppy make-out sessions happening all over the dance floor - but it will temporarily pause the post-3am ritual of drunken patrons having actual, full contact sex in the back of the bar in plain view of anyone who doesn’t have enough sense to listen to Koko Taylor sing I’m a Woman.


As you meet all kinds of people and learn more and more about tricky girls and craft beers, you will, of course, still be expecting to become a famous actress one day. You will devour details about the Jada Pinketts and Angelina Jolies in those same glossy magazines that you now know have at least three peoples’ blood on their hands. You will become absorbed in the minutiae of what Kirstie Allie eats, what Scarlett Johannson wears, and whether Britney really cheated on Justin, thinking that this kind of research will somehow parlay itself into you achieving the career of your dreams.

I think this kind of idol worship is common among people who don’t really know themselves or value their own point of view. In the absence of the blessing that is self-reflection, you will compare yourself to the beautiful people and you will always find yourself lacking. This is toxic, yes, but it’s also a stepping stone. Because, darling, the fact is, you are not yet ready to look at yourself as unflinchingly as you examine Salma Hayek. You are not prepared to ask yourself what you want out of your own life, what your own fantasy would look like. You try on many identities because you are scared to discover the truth about yourself.

By the time you turn 24, you will level up, but not before a string of bad decisions. At age 23, you will do a stint at a brew pub where you still have to carry lots of pints but thankfully not through a crowded dance floor. The people are nice and the money is good, but two of the bartenders fall in lust with you and you are so naive that you think they just want to be pals and are surprised when one of them gets mad that you don’t want to have sex with him. You decide that the staff’s obsession with Ultimate Frisbee and day drinking isn’t really you, either, so you will move on.

Oh! And the year before that, you worked at a different hotel bar where another bartender came on strong, but your boyfriend had recently dumped you, so you tried being this man’s mistress on for size. It’s fun at first, this new identity. Unfortunately, said bartender claims to have fallen madly in love with you and asks you to marry him (assuming he can get a divorce first, of course). At that moment, you will realize that not only are you not in love with or even attracted to this man, but that you actually don’t even like him. Given your patchy interpersonal skills, you will quit this job rather than face the mess you’ve made.

But back to being 24. This is the year you will arrive at Yoshi’s. Yoshi’s is a jazz bar/sushi restaurant combo in the San Francisco Bay Area, and you will quickly learn that, astonishingly, it gets even more pretentious from there. You will see that such a place attracts an audience of people who either have more refined taste than your average barfly or are pretending to in order to impress their dates/clients/in laws/college pals. You will be completely star struck when you realize that Shock G from Digital Underground is standing next to you in the crowded lobby, but you will decline, as usual, to outwardly acknowledge his celebrity.

You will catch on to the idea that this establishment calls for the cocktail waitresses to give more of an upscale escort performance than the regular call girl act required of you at any of the last four bars. Doing this job in high heels will feel unnecessary to you, and yet you will go along with whatever fantasy you are meant to pretend to offer if it means getting a twenty-five percent tip. The good news is you will get used to the heels. The bad news is that a tray full of martinis is quite top heavy and will regularly come crashing down during the quietest moments in any given show. Also, here will begin your life-long problems with back pain.

The furious 30 minutes that transpire between all of your 20 tables worth of customers sitting down at the exact same moment - expecting their food and drinks to come quickly - and the start of the show will give you nightmares for years to come. After you speed through gathering the orders from all those people who are very hungry and thirsty, you will pray to god that you can somehow deliver everyone’s stuff before the show starts. If the show is raucous - like when Arturo Sandoval plays, you’re good. But, if it’s a quiet, contemplative show - like the upright bass solos of Avishai Cohen, then you’re screwed. In a show like that, you will need to maintain near total silence as you deliver plates of sushi, bottles of sake, dirty martinis, and green tea ice cream to people who are mad that it took you so long. Also, you will need to crouch down constantly so as not to block the view of the people seated behind you.


On the plus side, you will have plenty of downtime in the following hour or so while Soon-Yi Previn watches her stepdad/husband take himself way too seriously while playing his little clarinet, or while a pack of hippies who spent their last dimes on these tickets and who don’t order anything sits in quiet reverence as Pharaoh Sanders sublimely plays his saxophone.

Very Important! DO NOT let the customers leave without paying. And, when they leave anyway, be careful running across the street to flag them down, as you are still wearing stilettos and that part of Jack London Square in Oakland is “historic”, so yeah, cobblestones.

As a cocktail waitress and bartender, you will see, in flashes of moments, some parts of yourself that you want to build up and others that you hope to slough off. Through the performance of borrowed identities in the service of making that month’s rent, you will begin a decades-long process of getting to know yourself, of gleaning, through reflections of yourself in the faces of your customers, slivers of who you are and chunks of who you’re not. You will see trophy wives whose lives you don’t envy and meet interesting intellectuals whose lives you do.


When you are 29, newly married and on your way to expanding your family, you will find yourself in your last bartending job. This one is a doozy, though, and while you thought you’d met every stripe of Italian restaurant owner out there, you will find an entirely new species at the impossibly modern Milanese restaurant in the trendy Fulton Street restaurant district in Chicago. Far from the southern Italian patriarchs with their ample waistlines and coterie of questionable friends that you are used to, these are fashion types who display couture clothes in the dining room and hire models as servers. They eventually get wise and start to hire regular folks, which is when you will come on board. From your perch at the glass tile-lined bar, you will marvel at patrons eating teensy $40 portions of pasta bolognese within inches of hanging designer dresses and wonder how red sauce never seems to fling in the wrong direction. Your boss is very nice - even if he and the rest of the staff are constantly high on cocaine - but it won’t take you long to realize that this isn’t you, either.

On your last day, you will be full of relief that you no longer have to do such embarrassing work. You will inwardly beam because you are on your way to social work school and will leave this unseemly career behind you. You will no longer cut limes or ready your speed bar or marry ketchups. Instead, you will study ego psychology and write papers about personality disorders. You will trade smoking cigarettes in the alley behind the kitchen for expensive salads with your new friends at the Water Tower Place. These new friends have never been cocktail waitresses and you like talking to them about jobs that don’t require you to keep your closet stocked with black pants and white shirts. You will try on a fancy new you, with framed diplomas in her office and after work supervision with mentors who have made a real difference in the world. You will become the president of the Graduate Student Association and start Loyola’s first School of Social Work anti-human trafficking initiative.


One day you start your internship at a group home for children who are wards of the state. You will wear modest clothes and sensible shoes. On your first day, you will go to the restroom and there will be no toilet paper. Naively, you will look in the cupboard under the sink, expecting to find an extra supply, certain that the reputable social service agency which has contracted with your school would never let these children - these poor kids who have experienced all kinds of heartbreaking trauma - go without a basic necessity like toilet paper. You will not find the toilet paper. What you will find is a pair of soiled underwear that someone had stuffed in the back, maybe because they couldn’t find the toilet paper, either. In 15 minutes, your new supervisor will barely introduce herself to you or you to the children before handing you a case file to read as you ride with her to a hospital to visit the 12 year old whose story you are now ingesting, a story that will contain a history so painful that just reading it will scar you for life. You will look down at your ID badge and feel like a total fraud.

However, you will take comfort in the fact that you are destined for a Noble Profession, one that will train you to help children and mend families. You will become a therapist -a pretty good one- and you will feel the waitress you peel off like a sunburn and the new you emerge from underneath, pink and dewy. You will let the girl that wore red lipstick and tight dresses with fishnets recede to the back of the closet, leaving room for the wardrobe of a truly serious person.

Then you will have children, and your relationship to your career and your identity will transform - over and over again. You have no idea what wives and husbands are supposed to do because you never had the chance to closely observe married people. And, as if work and relationship identities weren’t heard enough, your growing family will also grow your overhead and life in New York City will become even more expensive. To meet demands, you will work just as hard as you’ve ever worked but with much higher stakes. You will see that clients and children are demanding in equal measure, and you will start to miss the easiness of shift work.

Now you bring work home with you and home with you to work. And having kids is much more consuming than you could ever have anticipated, and now you have to manage yet another facet of identity - motherhood. You will try on the crunchy granola mom vibe, the cosmopolitan vegan mom look, and the harried working mom costume, but it won’t take you long to realize that being a mother is no less complex an identity than any other, and that there is no set uniform for you in it, either.

Now you are almost 47. You still sometimes buy the glossies, but your interest wanes as you cease to recognize anyone in them. You become curious about the girl who made theatre and danced to reggae music and could even be spontaneous sometimes. It only takes a few minutes to flip through the pages of celebrities and you swear - no matter how many different pictures of women in gorgeous dresses and bold lips there are - that they are all, in fact, the exact same person. But, to your surprise and delight, you are not.

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