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45 Shades of Hilarity

The Comical Chronicles of a Black Woman's Dating Misadventures in 2024

By Denise MillerPublished 19 days ago 5 min read

Picture this: A seasoned soul with the sass of a twenty-something, navigating the unpredictable terrain of dating in her forties.

This isn't just any journey-its a laugh-out-loud expedition through the highs, lows, and hilariously unexpected twists of modern day romance, as seen through the lens of a fabulous black woman at forty-five.

So buckle up, dear reader, and get ready to join me on this rollercoaster ride of love, laughter, and everything in between.

As I sit at my kitchen table, smoking a blunt and sipping on a glass of wine and staring at my laptop screen, I couldn't help but feel like a detective in a cheesy crime drama, except instead of solving mysteries, I am navigating the perplexing world of online dating.

With each click and swipe, I feel like I am peeling back layers of absurdity. uncovering gems like 'I enjoy long walks.......to the fridge' and Looking for someone who can handle my Netflix binges without judging my snack choices'.

Little did I know my foray into digital romance would be filled with more plot twists and laugh-out-loud moments than a reality tv show like 'Love and Hip Hop.'

Chapter One:

The Tom Brady Super fan Stalker

I arrive at the restaurant, nervously smoothing out my outfit hoping for a fun night out. As I sip my on my glass of wine, I notice my date approaching wearing a New England Patriots jersey with "Brady" emblazoned on the back, complete with face paint and a foam finger. "Yelling Go Pats!"

As soon as he sat down, there was no "Hello Nice to Meet You".

He launches into a long monologue about Tom Brady's stats, achievements and diet plan. I tried to nod and smile politely, but he was like freight train of football fanaticism and I was tied to the tracks.

Things took a bizarre turn when this man pulled out a life size cardboard cutout of Tom Brady's head, propped it up on the table using my glass of wine. He introduced to Tom Brad's head, then asked Tom if he wanted a beer.

I desperately tried to steer the conversation away from football, but Mike was relentless.

Every attempt to change the subject was met with a new Tom Brady factoid or a passionate defense of his legacy.

Chile I went to the bathroom, found the waitress paid my portion and left that fool sitting there.

Chapter Two:

The Cultural Clash: "Matt"

I matched with a guy who seemed great on paper. We decided to meet for dinner at a fancy restaurant. However, when I arrived, I quickly realized that he had never eaten soul food before. Watching this man attempt to navigate a plate of fried chicken and collard greens with a knife and fork was both hilarious and cringe-worthy. Needless to say, there wasn't a second date.

Chapter Three: "Andre"

The Surprise Package:

I thought for I had found the perfect match in Andre. We had been chatting for weeks and seemed to have a lot in common.

However, when when we finally met in person, I was shocked to discover that Andre was a package deal – he had brought his overbearing mother along on our date. Trying to navigate their conversation while also fending off his mother's intrusive questions made for a memorable and bizarre evening.

Chapter Four: "Gary"

The Fashion Disaster:

When I agreed to meet up with Gary , I was excited to finally meet someone who seemed to share my sense of style. However, when Gary showed up wearing a neon green suit and a matching top hat, I couldn't help but burst into laughter. Gary had apparently misunderstood my love for bold fashion choices, and the sight of him strutting around like a human highlighter was too much for me to handle.

Chapter Five: "Jamal"

The Awkward Encounter:

After weeks of texting, I finally decided to meet up with Jamal for coffee. But, when I arrived at the café, I was greeted by non other than Jamal's ex-girlfriend who had apparently decided to crash our date. I watched in disbelief as Jamal and his ex proceeded to have a heated argument right in front of me. It was like something out of a reality TV show, and I couldn't help but feel like I had stumbled into someone else's drama.

Chapter Six: "Derrick"

The Catfishing Catastrophe:

After weeks of charming conversation, I finally agreed to meet my online crush, Derrick. When I arrived at the bar , I was greeted by a man who looked nothing like his profile picture. In fact, he looked more like my dad's older friend than the athletic hunk I had been chatting with. Turns out, Derrick had used his nephew's photos to attract women online. I couldn't decide whether to be angry or impressed by his audacity.

Chapter Seven: "Eric"

The Unexpected Role Reversal:

When I matched with Eric, I was intrigued to meet someone who seemed to share my love for adventure. But, when we finally met up for a hike, I quickly realized that Eric was more of a "glamper" than a camper. He showed up with a portable espresso machine, a mini fridge full of gourmet cheeses, and a battery-powered hairdryer. I couldn't help but laugh at the absurdity of the situation as he attempted to set up a makeshift spa in the middle of the wilderness.

Chapter Eight: "Tyrone"

The Family Feud:

When I meet up with Tyrone for dinner, I wasn't expecting to be introduced to his entire extended family. Tyrone had failed to mention that it was his cousin's birthday dinner, and I found myself surrounded by a dozen loud and boisterous strangers. As I tried to navigate the awkward introductions and intrusive questions, I couldn't help but wonder if I had accidentally stumbled into a family reunion instead of a romantic date.

Chapter Nine: "Kevin"

The Time-Traveler:

When I started chatting with Kevin online. We hit it off immediately, bonding over their our love for '80s nostalgia. When we finally met in person, I was shocked to discover that Kevin had taken his love for the '80s to a whole new level. He showed up dressed head-to-toe in neon spandex, complete with a fanny pack. I couldn't decide whether to laugh or run for the hills as Kevin tried to serenade me with a boombox blasting George Michel- Careless Whisper.

Chapter Ten: "Anthony"

The Food Fight:

I thought I had found my culinary soulmate when I matched with Anthony online. We bonded over our love for spicy food and decided to meet up for dinner at a Thai restaurant. However, things took a turn for the chaotic when Anthony accidentally mistook the restaurant's signature chili sauce for ketchup and proceeded to douse his entire plate in it. I watched in horror as Anthony's face turned beet red and tears streamed down his cheeks, but I couldn't help but laugh at the absurdity of the situation as he frantically searched for a glass of milk to cool his burning mouth..

Chapter Eleven: "Ali"

The Extraterrestrial Encounter:

When I swiped right on Ali's profile, I had no idea I was about to be swept up in an intergalactic date that defied the laws of physics. Ali claimed to be an alien from a distant planet, and he offered to take me on a journey through the cosmos to explore the wonders of the universe. As we soared through the stars in Ali's imaginary spaceship, I couldn't help but wonder was I in the "Twilight Zone".

Hilarious

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Denise Miller

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    Denise MillerWritten by Denise Miller

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