Introduction: From Boardroom to Bedroom

Hi, I’m Dickson Sinfield, the star of this hilarious dating disaster series! I’m excited to share all the crazy adventures and knee-slapping tales that have made up my love life so far. I mean, my dating history is like a never-ending episode of “The Bachelor,” but with way more drama and fewer roses. And let me tell you, Cupid must be a comedian because he keeps sending me guys who are more absurd than the last. But, as much as I love to laugh, the stories in this dating memoir also serve as cautionary tales about the pursuit of love, the significance of safety in romance, and—most importantly—a lighthearted lens on LGBTQIA+ topics. So, fasten your seatbelts and brace yourself for a whirlwind ride of entertainment and enlightenment!

Silicon Valley to Beirut Bloopers!
Beirut, 2023: where economic turmoil and political mayhem share the dance floor with unforgettably wild parties. Somehow, I found myself in the midst of this chaos when my company, with impeccable timing, decided to send me to Lebanon, just as I was getting cozy in San Francisco. I had even snagged the perfect man in the city by the bay: tall, a top (or so he claimed), and a successful tech guru. Securing this perfect man was no small feat, especially after weathering the storm of Grindr letdowns. In this day and age, and in a city teeming with tech-obsessed androids and newly rich men like San Francisco, finding a single man in your 30s feels like hitting the jackpot in the most exclusive, no-strings-attached lottery. But no, destiny had other plans, and off to Lebanon I went, leaving my San Francisco beau behind, wondering if he’d mistaken “long-distance” for an “open relationship” as I did. Eventually, we broke up, via Zoom.

Taboo Tango: Gay CEO Chronicles!
Picture this: A dashing, well-groomed gay CEO with a penchant for order and a taste for adventure, takes on the world of dating in a city where “taboo” is an understatement. Sounds like the beginning of a gripping reality show, doesn’t it? Well, my dear reader, you’re in for a treat. Welcome to my life.

Hummus and Hips

Ah, let’s start with my heritage—Arabic, you see, my parents immigrated to the US long before I was born, and I’ve never actually lived in the Arab world. My knowledge of the region is essentially a mishmash of hummus and tabbouleh cravings, a half-remembered Poli-Sci 101 elective from my college days (which probably involved more doodling than note-taking), and the Arabic music my aunts would blast during family gatherings back in California. Oh, and let’s not forget those awkward dance sessions where they’d coax me into shaking my hips, proving that rhythm isn’t necessarily a genetic gift.

Don’t Ask, Don’t Tell
Navigating my fabulous gayness in an Arab American family is an experience in itself—picture a sitcom with a heavy dose of denial and a sprinkle of “don’t ask, don’t tell.” It took my parents almost two decades to come to terms with my sexuality, but we’ve reached a point of acceptance that’s akin to the military’s former policy. They’ve met some of my boyfriends, and my dad even befriended a few, but when it comes to what we do behind closed doors, the conversation remains off-limits, thank heavens.

Family Fables
Ah, my extended family, the kings, and queens of denial. They’re so good at pretending, they could fool a magician! Despite me being out and proud, they still pretend not to know. My dear aunt, God bless her, once commented on a Facebook picture with my boyfriend, saying, “Glad you two are like brothers.” And in true denial fashion, they can’t help but occasionally drop not-so-subtle hints about me marrying a woman someday. It’s like they’re trying to convince themselves more than me. But, hey, the juggling act of cultural expectations and living your true, authentic self? It’s like a never-ending performance at the circus, but instead of clowns, it’s just me!

Academic All-Star, Dating Detours!
I’ve always been a perfectionist—well, in everything except dating, that is. Throughout my academic career, I was an A+ student, acing tests and assignments in high school, college, and even grad school like a pro. I snagged my first internship with Microsoft before I could even legally toast to my success, and I’ve since scaled the tech ladder with the finesse of a nimble-footed mountaineer, leapfrogging from office boy to CEO. But when it comes to my love life, let’s just say my report card might look a little less impressive—more “needs improvement” than “exceeds expectations.”

Navigating Beirut’s Queer Quagmire!
You might think that being a successful Arab-American businessman would make me a catch in any city, and you’d be right. I have had dates, hookups, and relationships in almost every major city in the world, of course, villages and small towns too; and oh yeah, and in between, on a train once. But when I relocated to Beirut, it was as if the universe said, “Oh, you think you’ve got it all figured out? Hold my glass of gin basil (A drink that has become my favorite since I moved to Beirut).” Suddenly, I found myself navigating a minefield of culture, closeted desires, and comically bizarre characters, all while trying to maintain a semblance of normalcy in my professional life. I must admit, my track record with closeted and straight-ish men isn’t exactly stellar. We’re like magnets, irresistibly drawn to each other—maybe it’s my DNA’s way of connecting with my roots through a twisted game of romantic roulette?

Curious Connections
As an Arab American, I was well-acquainted with the region’s conservative stance on homosexuality, but I also couldn’t help but notice the curious man-to-man bromance that seemed to flourish here. I mean, you’ve got guys holding hands, sharing motorcycle rides like it’s the most natural thing in the world, and even kissing (Note: Lebanon is a triple-smooch society. Three kisses on the cheek). It left me pondering, with a sly grin and a raised eyebrow: do these bros take their bonding to the next level, too? You know, swapping more than just bike rides and handshakes? Wink, wink.

First-Class Flirting at 30,000 Feet!
As luck would have it, my jaunt to the vibrant city of Beirut commenced with a handsome Lebanese gentleman gracing the seat beside me on the plane. His flirtatious demeanor was a bold proclamation, as if he were the official ambassador of Lebanon, exclaiming, “Welcome to the party!” His eyes twinkled with mischief, and his charm was as intoxicating as the finest arak.

Friendly Banter or Flirty Seduction?
The line between friendly banter and playful flirtation was deliciously blurred, and I found myself questioning his orientation. Was he straight? Gay? Bisexual? No matter the answer, he certainly knew how to enchant and captivate.

As we swapped numbers, I couldn’t help but let my imagination run wild, pondering the unexpected adventures that might be waiting for me in Lebanon. If this chance encounter was any indication, the land of cedars had a few delightful surprises hidden up its sleeve.

Beirut’s Grindr Buffet: Bottom’s Dream Come True!
Stepping off the plane and firing up Grindr, I discovered a buffet of burly, macho men – a feast for the eyes and a tantalizing taste of what Beirut might have to offer. As a proud bottom, I’ve always had a type: tall and preferably larger than life. Scrolling through the grid, it seemed like my fantasies might just come true in this city.

Seductive Welcome!
Enter the immigration officer with his come-hither glances, making me question if flirting between men was a national sport in Lebanon. And then there was the hotel receptionist, exuding an unmistakable gaydar-pinging aura, hinting at escapades yet to come in a later article.

Looks That Can Welcome!
Perhaps my looks played a part in my unexpected Beirut welcome. You see, I’m in my mid-thirties, but people often think I’m younger, thanks to my twinkish charm and brown eyes that seem to have their own gravitational pull. I’m diligent about my daily workouts and eating healthy, with a penchant for my newly regular drink, gin basil. And I don’t smoke; in fact, that’s one of the things that would disqualify a guy for me. As the CEO of a tech company, I’ve developed a taste for dressing in black – it’s sleek, sophisticated, and never goes out of style. Classy bars are my preferred haunts, while crowds are my kryptonite. I take grooming seriously, ensuring that my nails are always immaculate and that my skincare regimen rivals that of a Hollywood starlet. Aging and I are in a constant battle, but so far, I’m winning the war.

Flirting for Escape?
Now, I can’t help but wonder if there’s more to these flirtatious encounters I had been experiencing since arriving in Lebanon. Maybe the locals are eyeing my foreign passport, a golden ticket out of their failing state. Or perhaps they can smell the money in a crumbling economy. Regardless, I can’t deny the thrill of the chase.

The Cheeky Side
I’ve got a little secret to share – I may look proper on the outside, but inside I’m a wild child. There’s no shame in love or sex, and I have an insatiable appetite for it all – relationships, dates, and yes, even sexcapades. Variety is the spice of life, after all! But don’t get the wrong idea, I value quality time with the people I’m with, and when I’m in a relationship, I’m a faithful partner (most of the time). And no, I’m not into quickies or full of myself – I just like to take my time and “assess” (pun very much intended) and perfect each date. After all, life’s too short not to embrace the cheeky side of things and revel in the humor of it all.

A Game for All-Star Players!
So, what’s the deal with Beirut? In a city that seemed determined to break all stereotypes, I quickly learned that “sexo-flexibility” was the local sport of choice, and as it turns out, I’m quite the all-star player in this tantalizing game of twist-and-bend! Join me on this uproarious ride through the passion and peculiarities of Lebanon, starting with a suave Frenchman who stole my heart…and left me saying, “Oh là là!

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