Upton's 5 Gay Dating Rules (Navigating Dating Dealbreakers)
- Upton Rand
- 5 days ago
- 7 min read
Updated: 2 days ago
A friend recently confided in me that the guys he was dating weren’t meeting his “checklist,” and I couldn’t help but reminisce about my 20s. Back then, I was that arrogant guy—drunk, armed with a comprehensive list of dating prerequisites. My “Maxims of Attraction”? “No cops, Republicans, closeted men, bisexuals, or military.” Classic wasted college senior confidence. It wasn’t until my early 30s that I realized how these absurd limitations had prevented me from forming meaningful connections, leaving me alone. Even now, whenever I look back at the men in this post, I can’t help but feel a sense of connection with them, as if they were/are ghosts clinging to me for dear life still to this day.
My coping mechanism became dark humor—laughing at my missteps. It’s a tricky art: balancing chuckles with the sting of missed chances. The humor is organic, absurdity speaking for itself, rooted in honesty. These five stories aren't just cautionary tales; they’re odes to the ridiculous limits we set before meeting someone worth loving. Before I jump into things just a quick reminder that the field guide is currently running a fundraiser to help cover expenses during pride month, please consider swinging by our store and picking up one of our limited edition fundraiser shirts. It helps keep the lights on and means the world to me and Max. Now let’s get into my dumbass in my 20s and my unreasonable dating dealbreakers.
🔹 The Rules - and Dating Dealbreakers sI used to Swear by.
My freshman-year DUI disaster at Michigan State set the stage. Eighteen, alone, reckless. One freezing night, wasted at a party, I wandered coatless into an East Lansing cornfield. A farmer found me naked and lost. I woke up in jail.
My parents clueless, phone dead, I expected disownment so I was partially relieved, but mostly crying and terrified. My only call was to Nick, a family friend and former small-town patrol officer where I grew up. He showed up like a renegade hero. His kindness, despite his past badge, should’ve floored me. Instead, it fed my shame. Though now a corporate lawyer, he bailed me out, handled officials like a pro. Grateful? No, too mortified. I only saw his law-enforcement past, even when he made me pancakes later. That "no cops" rule was already tattooed on my brain.
Years later in San Diego, swiping on Grindr, I matched with a campus police officer. The moment he said "cop," I deleted his number. Haunted by the cornfield, I couldn't face a uniform; it meant reliving shame.
Childish, I know. He could’ve been stable, honest—balancing my chaos. But shame and Nick’s past blinded me. My embarrassment wrote the rule: "No cops ever."
If "Rule 1" showed up today? I'd slame the door right in the rules face.
Back in Cleveland, scrolling profiles, I saw Jack’s grin. He messaged; we met for coffee near Playhouse Square. I was hungover; he, magazine-cover perfect. We clicked, trading post-grad woes. I felt alive.
Lazy Sunday mornings and takeout burger evenings watching the Cavs followed. Conversations deepened from beers to politics. One night, Cavs losing, Jack confessed: "I’m a registered Republican." Time froze. My Cleveland-raised fire ignited—"Republicans want to snatch my rights!" My upbringing had cemented a tribal us-versus-them mantra. The name Jack is rare, everytime I hear it I still feel his hand on my leg.
"I can’t—" I mumbled, bolting before he could react, half-eaten burger in hand, high on "political purity." A darkly comedic exit. Walking down Euclid Avenue, Playhouse Square lights mocked my narrow-mindedness. Was Jack perfect, sans party? Hell yes. Funny, generous, easy company. But "No Republicans" was carved into my DNA.
Absurd self-sabotage. Jack deserved better; I deserved a reality check. Voting isn't a crime scene. Love isn't an ideology. If "Rule 2" reappeared, I’d remember: human sides are the only ones worth choosing. Another connection sacrificed to tribalism.
Before the guide, my marriage and my slow slide into demisexuality, I never met guys organically. All filters, JPEG preening. True connection seemed like a unicorn. Then, David, at the NMU gym back in Marquette—no filters. His "Run Python, Not People" tee screamed "unfiltered."
Our bond was a slow burn, fueled by muscle reps and code. Weekends jogging Lake Superior's shores, his hatchback’s EDM rattling my teeth, his cluttered apartment our sanctuary. We collaborated on apps, tasted possibility. Evenings: takeout burgers, Python library debates—TensorFlow vs. PyTorch—laughter over my sloppy scripts. Something real stirred.
Then that night. He paused our show: "Upton, I’m not out. My family won’t accept me." Low, raw. My chest tightened—faulty code loop. Fear sparked a shutdown. "I…this isn’t going to work," I managed, turning away.
Out into the Marquette night, mind rewinding. 99% sure I loved him, but he fit my box. I ghosted him—silence like an unsent pull request. For days, his laugh, his relaxed shoulders, his hand on the wheel—all replayed. A neon sign flashed regret. Brilliant, kind, stunning—and I let an arbitrary rule cage us.
I should’ve stepped closer, let the slow burn become a wildfire. Instead, I locked my door, leaving him unacknowledged. That cage still creaks, an ache for unfinished code and unclaimed love. Fear of his "complications" complicated my own life more. I can still feel David with me to this day despite not speaking for years. He was an amazing person.
In my twenties: Vicodin went down like Pez, vodka like water. In that haze, I had another stupid rule: no bisexual men. Childishly, I saw them as closeted cheaters juggling wives, kids, Grindr. Bisexuality, to me, meant betrayal: "He's bi, he'll leave me for a woman."
Dating was a digital cage match. Then Chris, at MSU's student lounge. Hungover, I saw him with political science books, flipping a bilingual text, he was dual lingual in Russian. Dark eyes met mine. "Shit," I thought, "not in my league."
Stale coffee, shared cigarettes, bonding over skipped classes. A local, his conservative Catholic-Latino family made "coming out" a nonstarter. His quiet insistence, "one day, people will understand," disarmed me. Summer drives in his Honda, Beethoven rattling, the engine composing symphonies.
Nearing graduation, Chris was different. He saw past my ego, my fear of labels. Late-night study: he debugged my scripts, I helped with his Cyrillic. Greasy pizza, laughter. Something real stirred, lost since childhood shame over a first crush.
Fall finals, his confession: "Upton, I’m bisexual. Dated women and men. I exist between worlds." My heart, a server on fire. Stereotypes echoed: bisexuals can't be trusted. Panicked, I stepped back, muttered about "space," brick walling my heart.
An insincere smile, chest tight with regret. I told myself I was preventing competition with Women™—that phantom third party. Truth: terrified his closet would be my cage. Ghosted. Weeks of replaying library laughter, his bright eyes, his hand on my laptop. 99% in love, crushed I’d walked away from someone who didn't fit my mold. Maybe bisexuality was a bridge, not a barrier—an invitation to unlearn biphobic lines.
A quiet ache remains. Where is he? Georgetown, last I heard, weaving policy magic. I hope he’s free, knows he deserved braver. My own biphobia, masked as self-preservation, cost me.
Eighteen, slinging espresso at my family’s Marquette roastery when Jason, an NMU summer student, waltzed in. I used to do this thing where I judged guys on their coffee orders. For example— My coffee judgment: double espresso—tough; but if you ordered decaf or sweet blends—no chance. The first order I ever took for John, a double espresso. He caught his double like a lifeline. Different. Crisp ROTC fatigues, polished boots, oak jawline. Each morning: espresso, a dare of a grin.
Weeks later, he asked me to teach him to use his home espresso machine. I agreed, expecting incompetence. One sunday afternoon when he returned from field training he summoned me over. As we stood in his disheveled college kitchen we locked eyes. "Show me," he said. I demoed grind, tamp, froth. His smirk: "My turn. White Russian?" Never had one. The smooth vodka-Kahlúa-cream mix erased inhibitions. Soon, daily espresso lessons, nightly whispered promises—our bedroom routine.
Sacred Sundays: John returned from field exercises—dusty, buzz-cut, orders I couldn’t fathom—pulling into the roastery lot. He'd drive us to our cathedral, his small college apartment. He’d shed his uniform top; I’d trace his ribs—my GPS from loneliness to lust. Fatigues like a second skin, pine and adrenaline. For that hour, nothing else mattered.
One afternoon I got a text: "We need to talk." He rushed over and sat me down. "I might have to deploy soon," were the words I heard next. It was like aftershocks from a mortar shell—sudden, painful. His world: an assignment. Mine: apocalypse. His face flickered—pride, fear. My heart seized. "I’m not built for that," I blurted. His uniform and dignity cracked. I could instantly see the pain. This man loved me; he'd never loved another man, he said, but he loved me.
First light, my friend Sierra and I dumped his gear on his lawn—our breakup piñata exploding with shame. I said I spared him my fear; really, I unloaded terror of empty hallways, unanswered calls.
Mature? No. Regret it? With every espresso, every whiff of pine. Did he find someone who didn’t flinch? Darker than missing his uniform is the guilt of not saying, "I’ll face whatever—just stay." These rules, self-imposed prisons, created a gallery of ghosts.
Conclusion: Beyond the Bullshit Boundaries
Why the self-sabotage? Those rules shielded a bruised ego when I felt like fresh steak for a world eager to pick me apart. Each rule—fear, biphobia, homophobia, political tribalism—masqueraded as "protection," but was an excuse to shun differences. Cop meant judgment; Republican, healthcare debates; closeted, a cage; bi, phantom women; soldier, panic.
The price? Connections lost, and loves faded. Returning to my friend, we started the blog on who had lamented he wasn't finding men that checked all his boxes —"boxes don’t matter for the right one". Those were the 5 lessons I learned from these 5 men. I will never repeat these mistakes again. They cost me dearly.
Today, I’m tearing down those checkpoints. The lesson from my bullshit hit list. Love doesn’t offer a checklist. It’s rarely what you script; it’s often the one who ticks no boxes but sees you. Whether a cop or a Russian poly-sci student, if it feels genuine, I’m open today. Growing up means admitting real connection arrives in unexpected, goofy, messy packages—often the best kind. These were painful lessons from my past. Echos I can still feel in my soul.
I don’t know what love will look like. But if it’s real, I’ll ditch the pretenses, open the door, and thank whatever cosmic force for finally dismantling my ridiculous boundaries and for sending someone worth the risk.
My reminder— keep looking forward, keep looking up. Love doesn't always fit neatly into a box, and often will break every rule you thought you were sure of. Lean into it, because in my experience when love comes calling you shouldn't send it to voicemail.
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- Upton and Max
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