Unveiling Authentic Connections: My Week as a Trans Woman on a Dating App

Due to the number of shares the previous post 7 Days, 156 Matches, and 0 Potential Boyfriends: My Experience as a Dating App Virgin had, I went ahead and explored the bizarre world of dating apps for the second time with a twist.

DISCLAIMER: I am a single bisexual female posing as a trans woman on a dating app for research purposes. Throughout the week, I immersed myself and tried to keep in character with the majority of the folks I interacted with. I discussed writing this article with a wonderful friend, Stephanie, a trans woman. Aside from that, I spent many evenings binge-watching YouTube videos and reading case studies. I want to be as realistic as possible, ensuring that anything I do is appropriate and won’t offend anyone.

Greetings, fellow digital daters! Strap yourselves in for a hilarious journey as I recount my week-long escapade as a trans woman on a dating app. From the absurd pickup lines to the questionable profile bios, join me as I navigate through the maze of online dating in search of authentic connections. Get ready to laugh, cringe, and maybe even find a glimmer of hope in this wacky world of swipes and matches.

The Art of Crafting a Fabulous Profile: Putting the “Fun” in “Fundamentally Awesome”

Creating a captivating dating profile as a trans woman requires just the right blend of glamour and sass. Unfortunately, I failed at that department. At Antiland there was no option to upload selfies; instead, you can select whatever animals are available as your avatar. If you want to write a bio, there is a space available. Mine was rather threatening than inviting. But these two lines undoubtedly warned matches that they were in for an entertaining journey.

Unveiling Authentic Connections: My Week as a Trans Woman on a Dating App
Antiland Profile

The Perils of Swipeville: Where Puns and Pickup Lines Collide

Ah, the land of swipes, where puns and pickup lines reign supreme. As a trans woman, I encountered some unforgettable experiences. One match declared, “Are you a magician? Because whenever I look at your pictures, everyone else disappears.” While I appreciate the effort, my dear suitor, cheesy pickup lines aren’t exactly the key to my heart. But hey, at least it provided a good laugh!

The Unwanted Goods: The Unsolicited Portraits of a Certain Human Body Part

Ah, the unsolicited d*ck pic – an unexpected masterpiece that leaves you wondering if the sender mistook you for an art connoisseur instead of a humble smartphone owner. In this moment of sheer surprise, take a deep breath and embrace your inner curator. First, evaluate the composition: Does it have a proper lighting setup? Next, consider the subject matter: Is it an avant-garde exploration of angles or an accidental landscape photograph? Finally, don’t forget the critical critique stage: Craft a response that will make the sender question their artistic choices while maintaining your dignity. Remember, when life hands you lemons—or in this case, unsolicited lemons—use them to add zest to your ever-expanding collection of bizarre experiences!

Unveiling Authentic Connections: The Good, the Bad, and the Hilariously Bizarre

In the midst of the digital chaos, I stumbled upon a few authentic connections that had me giggling like a schoolgirl. One match shared my love for terrible ’90s movies and insisted on reenacting scenes from “Clueless” over a video clip. It may have been ridiculous, but it was refreshingly genuine. There were also some who were intrigued, and I had to explain how the transition went. Few even asked if I could send them a photo… Nice try, sweetie, but na ah. And then there were the matches who mistook me for a transatlantic pilot because I mentioned “trans” in my introduction. Note to self: clarity is key!

There were times that I broke character as I genuinely wanted to get to know the person. This one though, I swear he’s an absolute daydream (with a very sexy smirk). What? Isn’t there always an exception to the rule?

The Art of Ghostbusting: Adventures in the Mysterious Land of Ghosting

Ah, ghosting — a modern-day vanishing act that would make Houdini proud. As a trans woman, I encountered my fair share of ghostly encounters. It’s like signing up for a haunted house tour, except the ghosts are real and they have a PhD in vanishing without a trace. You start with a hopeful conversation, feeling like you’ve found the yin to your yang, the peanut butter to your jelly. But then, poof—they vanish faster than a magician’s assistant. It’s as if they enrolled in Hogwarts and majored in Disapparition 101. Maybe they were just scared of your dazzling charm or the sheer gravitational pull of your magnetic personality. Whatever the case, remember that when one ghost exits stage left, another potential boo may be lurking in the wings. So chin up, my darling, and keep swiping. After all, love might just be a ghostbuster away!

Lessons Learned: Laughing, Loving, and Embracing Authenticity

My week as a trans woman on a dating app taught me invaluable lessons wrapped in laughter and sprinkled with authenticity. I learned that a witty sense of humor can be the ultimate icebreaker and that true connections go beyond the superficial. Embracing my uniqueness and refusing to settle for anything less than genuine love and acceptance became my guiding principles.


As I bid adieu to my week-long adventure as a trans woman on a dating app, I can’t help but chuckle at the absurdity of it all. Amidst the hilarious encounters and questionable pickup lines, I discovered that authenticity and laughter are the secret ingredients to forming genuine connections. So, my fellow digital daters, embrace the humor, swipe with confidence, and never forget that you are a unicorn in a world of ordinary horses.

pride month banner 001 Unveiling Authentic Connections: My Week as a Trans Woman on a Dating App

Polly Amora

Polly Amora is the señorita behind GoldenIslandSenorita.Net. A corporate warrior by day, and a perpetual explorer by heart. She is a lifelong learner who is very outgoing, speaks four languages, loud & outspoken, and loves to have adventures in the mountains, on the beach, and in the city. You can throw her anywhere, and she'll handle it like a pro. Ice cream and bourbon are two of her weaknesses.


  1. I love the convenience of dating apps, but man, the ghosting is real. It’s like people forget there’s a real person on the other end of the screen.

    1. That’s true, I agree with that. Haha!

  2. I never realized how picky I could be until I started using dating apps. Suddenly, the tiniest details become deal-breakers.

    1. Even though I’ve only used dating apps for research, I still struggle with deciding who to swipe right on or hit the “accept” button for when someone sends me a DM. It’s tough out there, even for us researchers! lmfao

  3. Had my share of bizarre first dates, but hey, at least they make for great stories to share with friends!!!

    1. Absolutely! Bizarre first dates are practically a rite of passage but they make for some epic storytelling. lmao

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