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Worst Date Stories

February 13, 2020

Typically, when Valentine’s Day comes up, people think of a super romantic date with the stereotypical package of roses, chocolates, and expensive restaurants. On the flip side, people may think of an absolutely awful date experience they’ve had. While romantic dates have their great stories, people’s worst date stories are far more interesting to talk about, and that is exactly the direction we are taking here.

Starting off we have Kaitlyn, a dear friend and fellow coworker with a date story that not many people encounter:

“It was the summer before my junior year of high school when I had a very interesting date. Leading up to this “date” I thought we were just friends grabbing dinner, but I soon realized that his intention was a little different than mine. The telltale sign was him picking me up from my front door while also persisting to meet my parents. I had told my parents I was going out with the youth group because I did not want them to think I was going on a date, but they obviously realized that wasn’t the case once he got to my front door. After he proceeded to meet my parents, I got really nervous because I realized we did not have the same intentions. We had a plan to go get a casual dinner and I was more than ready to eat because I hadn’t eaten all day. Once we got in the car, he completely switched the plan and decided to go mini golfing. My grumbling stomach had another thought in mind, but I decided to let it slide and go with the flow. As soon as we arrived at mini golfing, the clear, blue skies quickly subsided and were replaced with stormy, cloudy ones. Our plan to go mini golfing was squashed with the unrelenting rain. So, we decided to plan yet another idea. Our second-best idea was to go bowling and I was excited because I am kind of stellar at bowling. After two games of ruthlessly beating him, I decided I needed to probably let him win at least one game. During the “date”, I was texting my two best friends giving them short updates with what we were doing so I could keep their curiosity peaked.

After bowling, we quickly grabbed ice cream from McDonalds (so romantic) and then he drove me home. My best friends were constantly texting me pawning for details, but at one point they just stopped. When he dropped me off, he walked me up to my front door to say goodnight to me. As we got to my front steps, I heard what I thought was an animal in my bushes wrestling around but I ignored it. As he hugged me goodnight, I then thought I heard whispering from the same bushes, but again ignored it. Immediately after I got into my house, I got a text from my friends asking how the date was which came to a shock because they were spot-on with the timing. As I texted them back with the details of the date, they sent another text saying that we needed to go out to coffee the next morning because they had something important to tell me, which instantly made me nervous.

The next morning, I got coffee with them and they proceeded to tell me that they were hiding in the bushes waiting for me to get home on my date. In addition to that, they were driving around town trying to figure out what bowling alley and McDonalds we were at. At first, I was appalled and then I couldn’t stop laughing. The guy who I went on a date with that night still has no idea. Overall, the date wasn’t awful, but the story behind it makes me want to cringe and laugh at the same time. The moral of the story is: get yourself friends that will hide in bushes to spy on your first date with a guy.”

Our next worst date story comes from another great comrade of mine, Alex Quan:

“I will be sharing a personal worst date story that I experienced back in high school. Unfortunately, what makes this date story bad was my own actions. It was my junior year of high school and there was this girl that I was starting to talk to. We had finally agreed to go on a date and the plan was for me to pick her up so we could go out to Sonic for milkshakes then head to watch a movie together. I had gotten all ready and even threw on an extra spray of cologne before my car decided to not start. I was so embarrassed, but ended up finding the courage to ask her if she could drive instead.

Soon enough, she picked me up and we made our way to Sonic. If I wasn’t already embarrassed enough, I came to the awful realization that I had forgotten my wallet. While I fumbled to find the words to explain my foolery to her and the Sonic worker, she intervened and paid for both of our shakes. If you thought this couldn’t get any worse, you are wrong. As the worker handed me the milkshakes, I let them slip out of my hands and the milkshakes took a tragic fall and spilled all over the inside of the car. Needless to say, the vibes were completely dead, and the date ended at that point as she dropped me back off to my sad car. Yup…rough times.”

Yikes, Alex! Our final date story is one that some of you may relate to from another friend of mine, Madelyn Mauck:

“It was my freshman year of college when I decided to go home for Thanksgiving. My family was asking the usual annoying questions about whether I’m talking to someone at school and whatnot. Then, the third day of Thanksgiving break, my dad decided to share that he set up a blind date for me. I assured my entire family that I did not want to go, but my parents said I had to. When the day rolled around, I was feeling nervous and uncomfortable, but I decided to be open to it. The person my dad set me up with turned out to be a childhood friend’s brother, which was a little awkward, but I was happy to see a familiar face. He took me to Panera for dinner, and things were going pretty well. I ordered my usual broccoli cheese soup in a bread bowl, and we began to talk about college and our plans for the future. I was just thoughtfully listening to his stories while scooping some bread from the side of my bowl, when the plastic spoon snapped into several pieces and soup splattered in my hair and all over my face. I want to know who told them it was okay to give out plastic spoons??? Anyway, we had a good laugh about it and he ran to grab a new spoon and napkins for me.

Later on, during the dinner, he was telling me a very personal story. I went to take a bite of soup, and then I realized I had just scooped a piece of the plastic spoon into my mouth. At this point, I didn’t want to interrupt his story because I felt really awkward, so I kept the piece of plastic in my mouth. I was awkwardly responding to his stories, with this giant piece of plastic in the side of my cheek, which made my voice sound weird and uncomfortable. Finally, I ended up taking it out really quickly while he wasn’t looking, and the rest of the date went pretty smoothly. I never went out with him again, mainly because I couldn’t get past the awkwardness of everything, but it was a good experience.”

So, if you end up getting that dream Valentine’s date, be sure to be thankful that it didn’t go as poorly as the ones just mentioned. On the flip side, if you do end up on the worst date ever, stay positive because it can only go up from there.

Happy Valentine’s Day from Student Activities!

Date stories by: Kaitlyn Skarstein, Alex Quan and Madelyn Mauck
Written and facilitated by: Mike Tammaro

Kaitlyn loves being able to write for the SA blog because she thinks it is important to share her voice. She loves being able to express her own opinions on important subjects that are relevant for students, faculty, and many others.



Alex is a Junior Business Communications Major and enjoys writing for the blog because of the opportunity to express his thoughts and interests through the medium of a blog! It’s a healthy way to share his opinions with others and hopefully start a dialogue with them.



Madelyn is a Junior studying Business Administration: Project Management. She enjoys writing for the blog, not only because it helps her develop as a creative writer, but because it gives her a chance to share her experiences through a platform she would not have without Student Activities.




Mike is a Junior double majoring in Finance and Economics and writes for the blog in order to expand my skills as a student. As a business major, the curriculum does not allow for a lot of creative writing, so being able to publish written work is freeing from my normal educational routine.