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.

8. Matt Not In AZ


Now we have entered the quarter final rounds. The top 8 will battle it out to be the saddest victor. Coming in at 8th place is Matt Not in AZ.

Let me give you some context for this story. It was October 2017 and I had recently gone through a breakup. I was visiting my friend Clara in northern California. Before heading her way, she convinced me to download Tinder again. You know… just for giggles. I wasn’t genuinely looking, I’ll be honest. But the potential to break my mind away from the thought of my previous relationship was tempting. So, I downloaded Tinder and began swiping.

Now, Tinder in my opinion is a game in its own right. But, the game we played was far more dangerous. One night while out on the town, we swapped phones to swipe for the other person. Clara and I are really close friends. But, although we have similar interests in food, movies and books, our taste in men has never been an area our interests overlapped. So this was going to be fun.

It probably did not help that we were out bar hopping. As fun as it sounds, I rarely recommending Tindering under the influence. Clara got several matches for me with conversations flowing shortly after. She is also an opportunist, though. So if a previous match sent a message, Clara had no qualms diving into a conversation with them either. Matt was one such conversation.

Just a friendly reminder that when the conversation doesn’t sound like my typical cadence, you can bet that Clara is responding.


Tinder, might I add, is a location based dating app used to connect people based on geographic positioning. I must have matched with Matt prior to leaving for California since his distance was much, much further than the “within 20 miles” metric in my settings–a distance difference he clearly did not notice.


Clara and I agreed– he had no business knowing where I was. All he needed to know was that his request was physically impossible.


Not entirely sure how he jumped from getting Mexican food to spending the night… Let’s even say that I wasn’t completely turned off by the idea of meeting a stranger at 2:30am. Let’s go a step further to assume I am not repulsed and terrified by the idea of spending the night with said stranger. His request still does not grasp the fact that I am still not in Arizona!


We did have quite a bit to drink that night. While walking the streets of the lively downtown, we ran into some of Clara’s coworkers who dragged us into a nearby dive bar. My first gin and tonic–heavy on the gin, light on the tonic– was served in a pint glass! And the drinks kept coming. Note the alcohol intake and still Clara had excellent grammar! Bravo!


Alas, Matt still did not comprehend the fact that I was not in Arizona.


Nobody says it better than Katarina Stratford in 10 Things I Hate About You. Her eye roll says it all. But, alas, I was not the one responding.


Instead, Clara gave him some pretty practical advice.


Thunderbird School of Global Management was listed as Matt’s education on his profile.


Ouch. His entire point was to defend his intelligence. Then, he uses the wrong homophones instead of “than” and “they’re” all in the same sentence.


Oh good! Clara is just as sassy as I would have been! Excellent.


What do you mean you “just noticed the distance”?? It was repeatedly pointed out to you in your quest to invite me over.


Or perhaps both. I do not believe those two situations are mutually exclusive.


Buddy… we had been asking ourselves the same. exact. thing.


Clara is getting feisty at this point. She has had it with Matt and his perceived level of intelligence.


Goodnight, Matt. And goodbye. Clearly.

10. Murdering Mormon


Up next in the top 16 countdown is number 10… The Murdering Mormon. I realize that this nickname is just as odd as it is unnerving. But, allow me to explain. If you have read some of my other posts, you know that I tend to start conversations with the same telling question: If you had to describe yourself using only one word, what would it be? I get answers like “driven”, “motivated”, “funny”, “exciting”… Usually adjectives that would entice further conversation. Rarely do I get nouns and even more rarely are they scary. But, along came Jacob…


Hm. Interesting first impression.


And alarmed I was. Who opens up a conversation with someone online and immediately jokes (or at least I hope it was a joke) about being a murderer? His response turned into the world’s worst segues.


At this point I am incredibly confused. I am not Mormon, but I am friends with many. It just comes with the territory of growing up in Mesa, AZ. Is being Mormon good for him? Is it bad? Do I meet some really creepy murder checklist if I say yes? Is it worse if I say no? Either way, the thread of conversation is splitting awfully thin.


He had a totally reasonable chance to explain his question. In fact, the connection with a mutual friend actually made sense. But he had to go and ruin it with the line “Good cause I don’t murder Mormons.” And that answered my earlier questions. Being Mormon would have kept me out of the line of danger. No was apparently the wrong answer if I wanted to keep my life. So, I guess that puts me back on the hit-list. And once again, in an attempt to change the topic, we are hit with a totally unnatural transition in conversation. I ignored the inquiry into my weekend and doubled-back to his murdering comments.



I don’t have any doubts in my mind why this man was single.


The mere fact that I am uncertain if he’s actually joking or just really disturbed should be telling. Perhaps if I had better survival instincts, I wouldn’t goad a potentially psychotic (let’s be fair, he self-described as a murderer before saying anything else) individual. But I cannot help it. My thoughts will be told, consequences be damned.

Once again, an excellent conversationalist. Knows when to transition in an out of topics seamlessly…


Perhaps I am beating a dead horse. Perhaps I should let it go. But I just cannot wrap my mind around the fact that this guy described himself as a murderer.


Curiosity may have killed the cat, but it could save the life of an unsuspecting internet dater.


Ohhh okay. He is joking. Totally just messing around. Making a mockery of the fact that women are always needing to be vigilant. Alright. I can sort of get behind that. Maybe he is just not very socially aware.


“Serial killers fascinate me” is definitely not how that explanation should have ended. At least he thinks they are evil?


Texting typos aside, it’s true. If a girl thinks that someone is a murderer or serial killer, she certainly will not swipe right just to tempt fate. I went out with, and ended up in a good relationship with, a guy whose profile listed 10 things about him. Number 1 was “won’t murder you.” Alright, playful insight. Addressing the situation in a joking way. I totally get it. Beyond that though, the topic of whether he would murder me just never came up. Just the fact that someone has matched with you indicates they show at least a little bit of interest. Don’t start a conversation with something that will instantly create a barrier between you and the other person. Especially if you already know that this is a common concern of the weary online dater.


Weird may have been boring, but I think I would have preferred that to the persistent thought of his murdering past. I never did risk my life to meet him in person. We would have never worked, anyway. There are too many differences between our schools of thought and brands of humor.

The search continues

14. Bad Teacher


In fourteenth place… we have the Bad Teacher story brought to you by Andrew. It started as a normal conversation. Certainly nothing to write home about.



Nothing out of the ordinary. Just regular small talk to wade into conversation intended to get to know someone.


“Thanks.” I acknowledged the compliment. In general, this is something with which I tend to struggle. I don’t know how to take a compliment and in that regard I’ve always felt socially awkward. Perhaps it’s social programming or widely held societal standards or just my inherent awkwardness at times. But it’s there. So, I acknowledged the compliment and tried to move on.



I wasn’t buying his story, but I wasn’t intending to call him out on it. I had barely started talking to the guy. Back then, when I first started the online dating venture, I wasn’t nearly as bold. Before I could even ask him clarifying details about that particularly ambitious line of work, Andrew once again redirected the conversation.


It was at this point my sassy side started to shine through. In general, I think this type of conversation is frustrating. There are so many implications with the “hot teacher” archetype. Regardless of my students’ assessment of my appearance (by the way, gross and I don’t want to know), they learn. I am just as vivacious with speech in my classroom as I am online. I really don’t accept any nonsense in my class. But the implication that is perpetuated by the “hot teacher” role, especially when used to flirt here, is that a student may have a chance to be with that teacher. Absolutely unacceptable, unprofessional and uncalled-for. And so icky. My profession is my passion and my livelihood. It is not some sick, twisted fantasy.



And once again here, accept the compliment and move on. My frustration is building, though. I clearly am not engaging in this line of conversation. So, once again I try to pivot to a more appropriate topic.


Yes! Okay! Now we have something in common. I love Game of Thrones– a show on which I could spend hours discussing. This will be perfect to expand our conversation.


Annnnnnnd… there it is. Again. I grew up playing baseball (no, not softball–perhaps a rant for a different post). Three strikes and you’re out, buddy. It’s time to shut this down. Clearly he isn’t picking up the fact that this raunchy teacher-talk isn’t going to happen.


Thanks, Andrew, for the conversation. Hopefully he learned at least one thing from this teacher: pick up better on social cues. On to the next…


15. No Chill Logan


In 15th place… No Chill Logan.

Logan has this name because he literally has no chill.

Logan, like many others, initiated contact by utilizing my love of mathematics. Typically, my profile always has a math quote from some professor. This accomplishes two tasks: 1) communicates my passion for mathematics and 2) scares away (some of) those who aren’t the brightest bulbs. Logan, however, was not dissuade by my passive assertion of my intellect.


All things considered, he probably would have been better off to just go for the pick-up line. Clearly there is one from Google buried in his opener. And pointing out that he “isn’t smart enough for it” wasn’t going to be doing him any favors. But, this is not why Logan made the cut in the tournament…

No, Logan made it to the Battle Royale of the top 16 because he has no chill. Note the time stamp on the Tinder message? 10:36pm.

I do not know what made Logan believe that responses to Tinder messages needed to be favorable and immediate. Somewhere in his mind, though, he believed that I should have responded to his message right away. Not even 12 hours later, he sent a follow up message… on a completely different dating app!

no chill logan 3

Seriously…? No wonder this lad is single. He has no chill and some control issues to say the least. I don’t appreciate guilt or negative communication being used against me to try to manipulate a conversation. I cannot imagine it works in his favor very often, either.


He apologized, in case you were wondering. And while I appreciate someone taking some ownership over their actions, I have no interest in associating with someone who instinctively jumps to hateful speech or manipulative tactics.

In fourteenth place is… Bad Teacher.