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Being An Affluent, Straight White Dude Is Actually Super Hard

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When you see me out gallivanting around the vineyards of Napa Valley or navigating the Mediterranean Sea with my extended cabin sailboat in my gingham oxford, khaki shorts, and casual driver loafers you might think you’re looking at a life-long resident of easy street. You look at my uneven tan lines from the country club as I walk my purebred golden retriever in my gated community and believe that I was born with a silver spoon of caviar shoved firmly up my sculpted-by-Equinox backside and get the rash impression that I have it made. But guess what, people born on the wrong side of the tracks? It’s not all steak dinners, $300 haircuts, and black tie galas. There are plenty of real issues for those of us that summer in Nantucket. Like that one hippity-hop, rotund fella Notable Smalls once said, “More money, more problems.”

For starters, I’ve developed a crippling amphetamine addiction since my mom and dad slipped the pediatrician a few extra bills to sign the scripts for an Adderall prescription when I was five rather than actually parent and discipline young Daniel. Twenty years later, and I need a dosage that no doctor will approve in order to just get out of bed and function like a walking corpse.

Because of this dilemma, I’m forced to turn to law-breaking individuals to get my fix. And due to my put together appearance and unbelievable wealth, keeping a dealer for more than one purchase is quite the monumental task. They don’t answer my phone calls or texts messages, and one guy called me a “narc” (whatever that means) to my face before refusing my business. Granted, I did also ask for just one ball of cocaine instead of eight so I could dip my toe into the waters of that world, so maybe he didn’t see me as a serious client. But he was a very rude man. Was it really necessary for you to slam the door in my face, Rodrigo? A simple “no” would have sufficed.

In contrast to those shady gentlemen, everyone else bombards my time with phone application pitches or tries to solicit stock market advice. Now is my name technically on a hedge fund? Yes. But that doesn’t mean I know how any of this Wall Street mumbo jumbo works. Whenever I show up to the office I just zone out during meetings and nod whenever the partners are addressing me. It’s like my father and his associates are speaking another language and I barely passed 9th grade English in boarding school.

At least my pops is starting to somewhat talk to me in the firm again. He’s been all bent out of shape since I chose to play club lacrosse at a state school rather than attend Wharton, and it was a four to five year window where I didn’t hear a peep out of the old man. Must be the way he shows his love. I can’t even remember the last time my parents held a conversation longer than ten seconds and they’ve been happily married for 35 years. They just throw back bottle after bottle of wine every day in silence. And by they, I mean my mom. Senior puts in a lot of late nights at the office. Always has. That’s why he could never make it to my little league games. Someone had to keep the lights on. And his friend Candy that I could never tell my ma about seemed to always have problems with pipes bursting. What a helpful guy my dad was.

As for myself, genuine companionship is hard to come by. Even at school, I had a bid to every fraternity before stepping foot on campus. Seemed odd. You’d assume they’d want to meet me first, after all. And when I did show up to the houses, they just kept asking about my family’s net worth and vacation homes. One kid even kept calling me “Billy Benefactor.” No other rushees were getting asked about their dads. I played sports in high school, too.

And, of course, finding any meaningful romantic relationship is virtually impossible. Fifteen minutes into meeting a young woman and she already wants a tour of my penthouse. And it’s never a long tour; usually just my bedroom. Weird that so many girls these days are cool with condom-less sex. Not that I’m complaining, but you’d think more of them would want to get to know me first or have me pull out. I suppose life’s not all that bad. This lovely lady that caught my fancy a while back is all of a sudden starting to hit me up out of the blue again. Gosh, it must have been 8 maybe 9 months since the last time we hung out. I don’t want to jinx anything, but maybe I’m finally catching a break on the love front.

Image via Shutterstock

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Dan Regester

Dan Regester @Dan_Regester is a Senior Writer, Podcast Host, and Video Guy for Grandex Media. He's Delco trash to the core and a UCF cinema studies graduate because he never got around to applying to an actual film school. Dan is a gambling man, crypto investor, and procrastinator. He enjoys long walks to the water fountain between bench press sets and is not a fan of the homeless, the elderly, or the Phoenix Airport. Email tips to

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