4. 10 Things I Hate About You

The ongoing bracket of the top 16 weirdest online dating experiences I had to date.

I realize it has been a long time since I hopped onto this site to jam out some of my dating impressions. With the whirlwind that was the most recent teaching year, I made plenty of excuses to prioritize other things. But, now that I am back, we enter the semi-final rounds of the not-so-sweet 16. Coming in 4th place is a story I like to call 10 Things I Hate About You.

This isn’t a story of me rattling of 10 traits I really hated about a guy but ended up loving. This also isn’t a story of a guy telling me 10 things he hates about me before ever meeting (though I wouldn’t put it past some of the people with which I have interacted). This, instead, is a story of boredom.

Honestly, I had reached a breaking point in online dating. I was seldom introduced to decent conversation and even less frequently met decent men. Throwing my hands up in the air, I resigned to treating the endeavor like a joke. What better face-saving tactic than to approach everything as if I didn’t care? And, if I am being completely honest, it turned out to be one of the most entertaining 24 hours I experienced with online dating in general.

See, I got the idea from plenty of BuzzFeed articles of women channeling their inner character and quoting from famous movies or TV shows. Some of my favorites include Sex and the City’s Carrie Bradshaw and questions from her sex column and lyrics from Taylor Swift songs.

My family constantly talks in movie quotes. We could carry conversations for hours just reciting lines to our repertoire of family-classics. So I was up for the challenge. But what movie would I pick? One of the movies I quote the most is the 1999 teen rom-com 10 Things I Hate About You. What can I say? I deeply relate to Kat’s sassy, quick-witted attitude. The results were amazing. Later I will share all of the conversations threads that resulted from my little experiment. For now, though, I’ll introduce you to just one.

Joseph and I had already exchanged a few words at the point I decided to start my game. Not much of a conversation had occurred. To give context to the first message, he knew I taught and it was the middle of August. School had just gotten underway.

Oh, Joseph… I wish I had.

Three question marks almost halted the entire conversation. So, I had to pivot the conversation using a line from one of the more serious scenes of 10 Things. Kat Stratford (Julia Stiles) is opening up and trying to connect with Patrick Verona (Heath Ledger). He pivots away from that question to a complement. Joseph, too, diverts the serious nature of the question, but not nearly as successfully.

At quick glance, you might be impressed that he took his “random facts” to somethings so math-related. Upon actually reading the response, it is easy to be floored by his lack of concept of size. Seventy-nine square meters?? That’s huge! Perhaps he just has an “engorged” perception of objects. Or, more likely, perhaps he just misspoke. Being in my 10 Things experiment, though, I had no room to call him out on his misjudgment.

Once again, a complete diversion of something serious. Though, how deep do you go in a conversation with a stranger online?

If the most real thing he had to share was about cracking his ankle, he has clearly lived a tough life.

“Am I that transparent” is typically followed by “I want you, I need you. Oh baby, oh baby,” but I didn’t want to give Joseph the wrong idea.

And, to be fair, many people find me to be intimidating. I wouldn’t go so far as to say afraid, though.

This is exactly why I did not want to continue with the previous quote. I’ll admit, I probably should have interjected with a new question or quote. However, this was the longest conversation drawn from my favorite movie and at this point I could not think of another line that would naturally flow with the conversation. I did my best to rein it back in an effort to redirect the conversation.

Okay. Now I almost feel bad for the guy.

Yup. Definitely feel bad. I have no idea how to respond with my limited choices.

Perfect. Laughter. So we have diffused the situation but once again pivoted to a conversational direction down a dead-end street. Let’s try a new path, then.

Here was my thought. Maybe he would interpret this exclamation as my need to vent about my circumstances. That, however, was not how he responded.

Aw man… this just really hammered the nail into the coffin. At this point, how could he possibly think that I am not being an asshole? I fully admit that I was being an asshole.

Why?! Are you not?!

fem·i·nism (noun) the theory of the political, economic, and social equality of the sexes

as defined by Merriam-Webster dictionary

But, that’s not what I could say, is it? Instead I went with my favorite response to “Hello, Katarina. Make anyone cry today?”

And with that, Joseph bowed out of the conversation. I truly hope it is because he found someone special and decided to end unresolved conversations with other women online. Something tells me that’s not the case, but we can only hope.

5. Telling Voice

While this story is not accompanied by many screenshots, the nature of the conversation was a bit chilling. That is how “Telling Voice” made it to fifth place in the Battle Royale of weirdest dating experiences.

It started relatively normal. He typed first and off we went.

“Guyfishn” had an interesting tactic, I’ll give him that. His photos were decent to look at as well. So, I temporarily took the bait. He was quite proud of himself.

I am about to launch into my patented sassiness. Tell him that opening with a fun question or silly quote is usually more interesting. While he did illicit a response, it is not as if the conversation was going to great places yet.

Now, here’s where it gets weird… after a certain point of back and forth communication, the app allows for an extended set of means by which to communicate. You can call through the app, send photos to one another, and apparently even send voice messages. With these new features unlocked, Guyfishn decided on one of those options instead of a regular text. Any guesses?

If your mind immediately went to “dick pic,” as I surely would have with that set-up, you are (luckily for me) incorrect. Nope. Guyfishn sent a voice message.

I’ll be completely honest. At this point, I don’t remember exactly what he sent in that first message. He said something along the lines of being upfront and honest; telling the truth in all situations. He was being a bit pompous, I recall.

But while I do not remember exactly what he said, I can tell you exactly how it felt listening to that voice message on my phone. Have you ever had an immediate, heart-wrenching, gut feeling? As soon as I clicked play, my alarm bells in my entire body went off. Who was this guy? Is he honestly who he claims to be? Why be so obnoxious about honesty and sincerity if he isn’t?

This is ridiculous, right? How can I be so skeptical with just one eighteen second glimpse into his vocal pattern? Still, that feeling wouldn’t leave. So, I dove into what I do best–research. Some reverse image searches and several articles later, I arrived at a reasonable conclusion. This guy is sketch AF.

The results of my research were as follows. I could not initially find any of his photos online in other locations besides this dating site. After a few minor tweaks my search query, I found his main image. It was linked to a comment thread on a random blog about Canadian actors.

Once I could tell that the profile in general felt manufactured, I delved into a search about why I had such an off-putting feeling in the first place. This guy didn’t sound like a 27 year old at all. If I had to guess his age just by listening to his voice, I would put him around 57. Apparently, a person’s voice actually says a lot about them. You can tell things from height to age to weight, just by talking to someone on the phone, with relative accuracy according to an article in The Guardian.

Then he sent another voice message. This time it was much more negative and manipulative. He was, in a sense, egging me on. Partial underhanded comments and partial challenge to give him the time of day. He pointed out that I better be who I say I am. Dude, we haven’t even held a legitimate conversation. Chill out. At this point, I had heard all I needed. The goosebumps were standing on end and the nausea was bubbling in my stomach.

He blocked me moments later. I am not surprised. I was honestly about to do the same. Hopefully he learned his lesson to not hide behind an imposter profile while chastising others who may be doing the same. Let’s be real, though. He probably did not learn that lesson. If anything, he may have learned not to mess with someone who knows how to do her research.

6. Dave and Busters

In 6th place of this Battle Royale of the most cringe-worthy dating experiencing is another classic story from my archives. This one is brought to you by the high-energy adult playground Dave and Busters.

Nick was incredibly awkward, but he seemed so sweet. His profile spoke beautiful poetry of the love he sought in this world. A bit verbose for an initial look at the profile, but still sweet. Maybe I had just jumped to some pre-conceived conclusion.

But between the lag in responses, your lateness to our first date, my migraine and throwing tickets at a child, I have come to a solid conclusion… Nick, you really were As Awkward as You Seemed.

The Beginning.
I wasn’t intending on you being that awkward. Sure, you seemed like you were “playing the game.” Someone must have told you once that responding too quickly meant you had “no chill”, that you would seem too needy and desperate. But there is also a length of time where that response lag is blatantly obvious. And you were blatantly obvious….

–continue reading–

It was best we never went out again. I can buy my own Red Bull, sure. I just shouldn’t need one to get through a date.

Follow the countdown to the top weirdest story on the Battle Royale. We are heading into the top 5 stories soon!

7. Ryan FICO


Coming in at seventh place is the story of Ryan FICO. I’ve told the tale of a Tinder profile often discovered year after year. But for those who have not read the original post, follow the link to see the story.

So… We Swipe Again

“When I first started online dating in 2015, I had some pretty hard and fast rules regarding the profiles I would say “yes” or swipe right on. When it comes to photos specifically, I use some loosely guided rules to govern my interactions.

  • Shirtless photo? Pass.
  • Photo with a bunch of women? Pass.
  • Photo with kids? Pass.
  • No photo at all? Hard pass.


This one particular person had a profile photo that seemed incredibly arrogant.”



Revisiting this story reminds me of some details I had previously neglected. When discussing why our conversation fell by the wayside (I cited his self-given list of flaws), I had mentioned that I didn’t even know what he looked like! It was then that he sent me a picture. It was a photo of him with his sister at her wedding. He even gave me a link to his YouTube channel offering strangers of the internet financial advice. Then it hit me… I had seen this very photo before. It was a deja vu moment that I couldn’t even cop to. Had I dropped off the planet because I just wasn’t attracted to the man behind the FICO score? It’s entirely possible. He wasn’t my type at all socially and the lack of physical attraction could have very well sealed the deal. I hope Ryan ultimately found what he was looking for.