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Gay Dating Patterns: My Shadow Journey to Vulnerability & Growth

Writer's picture: Upton RandUpton Rand

So my therapist hit me with some truth bombs yesterday that I'm still reeling from. Turns out I've been repeating the same gay dating patterns for years, seeing the same damn guy with different faces. Shocking, I know. I'm basically a clown car of bad decisions with a master's degree in picking emotionally stunted men. The universe's cosmic joke is that I keep attracting exactly what I put out – emotional unavailability wrapped in a nice jacket and the emotional depth of a puddle in the Sahara.


Speaking of putting out the wrong energy, let me confess something truly embarrassing: I never learned that you're supposed to bring a gift when you visit someone's home. Yes, I'm that guy who's been showing up to dinner parties for years with nothing but my sparkling personality and an appetite that could rival a black hole. In my defense, I grew up with male role models who considered emotional intelligence an oxymoron and in a town so isolated that social graces were about as necessary as swimwear in Antarctica. But hey, I found a YouTube channel called "The Male Gentleman" because apparently, I need the internet to teach me how to adult at thirty-something. Just add it to the list of basic human skills I somehow missed, right between "maintaining healthy boundaries" and "not texting exes at 2 AM."


So here's my universal apology to anyone I've neglected this etiquette with over the years: I'm genuinely sorry for being such a clueless idiot. All I can say is I'm trying to do better, and if something slips through the cracks again, please let me know instead of silently judging me (which I totally deserve). But rest assured, I'll never show up open-handed again. Consider this my formal declaration that I've finally joined the ranks of functioning adults who don't arrive at your doorstep like they're entitled to free food and hospitality. Better late than never, though "late" in this case means "embarrassingly behind everyone else who figured this out in their twenties."


If I can't be vulnerable without breaking out in hives and running for the hills, how the hell am I supposed to attract someone who doesn't treat feelings like they're radioactive waste? It's like showing up to a potluck empty-handed then wondering why nobody wants to share their food with your freeloading ass. These therapy insights about my pathetic gay dating patterns have been both painful and necessary for my personal growth, if "growth" is what we're calling this dumpster fire of self-discovery.


Meanwhile, it seems every gay man in Cleveland except me is in a committed relationship. Did I miss a memo? Was there a meeting where they handed out boyfriends and I was busy rewatching Schitt's Creek for the fifth time like the sad sack I am? After dissecting my friends' relationship dynamics like some deranged relationship coroner with nothing better to do on a Friday night, I've identified two types of successful gay dating patterns: the stoic Type A paired with the warm Type B. The revelation that knocked me sideways? I'm the stoic Type A – emotionally constipated but great with spreadsheets and organizing the hell out of a Tupperware drawer – and I need someone who actually knows how to express emotions without requiring an interpreter, a diagram, and three rounds of tequila shots. It's not exactly groundbreaking psychology, but it hit different when I realized I've been fishing in the wrong emotional pond with a net full of holes. The gay dating scene demands this kind of authenticity if I ever hope to find a genuine connection instead of another six-week situationship that ends with me pretending to be busy until they get the hint.


After spending actual paid sessions figuring out what I want in a relationship, I've come to understand that safety and stability top my list, which is hilarious considering my dating history looks like a case study in chaos theory written by a monkey with a crayon. It's like I've been saying I want a calm lake while exclusively dating tsunamis and then wondering why I'm always emotionally drowning. Self-awareness doesn't mean anything without action, though.


So here I am, trying to practice vulnerability (writing this mortifying blog post counts, right? Or is it just another form of self-flagellation?), being upfront about wanting stability (sexy as a pair of tighty-whities, I know!), and remembering to bring thoughtful non-alcoholic gifts when I visit someone's home. Being in recovery has taught me a lot about showing up authentically—both literally and figuratively. The bar is literally on the floor, and I'm still tripping over it like I'm competing in the Olympics of social ineptitude.


The plot twist? I'm actually seeing someone really nice right now. Someone who makes me question all of my cynical observations about dating and relationships—in the best possible way. I find myself constantly second-guessing: Am I being authentic enough? Am I allowing true vulnerability? Am I repeating old patterns? But that questioning itself is growth. The fact that I'm aware enough to ask these questions means I'm not the same person who stumbled obliviously through relationships past.


My journey of social etiquette learning and relationship self-awareness continues, but at least now I've got a roadmap, even if I'm the world's worst navigator with a broken compass and no sense of direction. And maybe that's the most important lesson—growth isn't about having all the answers. It's about being willing to acknowledge when you've been getting it wrong and having the courage to try a different approach. Whether that's bringing a damn gift to a dinner party or allowing myself to be genuinely vulnerable with someone who might actually deserve it.


Speaking of which This is 100% Real- and if I dropped the ball with you please do use it. It's not really limited to housewarming gifts, it's anything.

 

🚨OFFICIAL ETIQUETTE DEBT COLLECTION FORM 🚨


Did I ever show up to your home empty-handed like some kind of etiquette criminal? Instead of awkwardly reaching out to everyone I've ever visited (mortifying), I've created this much less embarrassing public form. Please fill it out and let me ship you out something to make it right, and accept my sincere apologies. 

Upton Rand (Heathen in active reform)






P.S. If you're also socially challenged and somehow made it to adulthood without learning basic etiquette (please tell me I'm not alone 😩), check out The Male Gentleman on YouTube. He's my new etiquette guru, teaching me how to pretend I wasn't raised by wolves. Better late than never, right? 🤦‍♂️ Consider this my public service announcement from one disaster human to another. 🥂 (Mine's sparkling water, but you do you.)





I was on Amazon and looking for a solid male etiquette book. I found it, but I also found this one. It looks super interesting so I picked it up as well.



Blue book cover titled The Gentlemen's Book of Etiquette and Manual of Politeness by Cecil B. Hartley, featuring elegant text. For gay men learning how to be a gentleman late in life. Or social etiquette at any time. dinner parties, conversations ect.
I was on Amazon and looking for a solid male etiquette book. I found it, but I also found this one. It looks super interesting so I picked it up as well.


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