Embarrassing Teacher Moments: Awkward Dates and Break-Ups


Erika Ackley, Managing Editor

Amidst the love-filled atmosphere of Valentine’s Day one can’t help but remember all the awkward and embarrassing moments that can happen to just about anyone when it comes to relationships. From horrifying to uncomfortable, these teacher experiences are sure to make you reconsider the dating world and Valentine’s Day altogether.

Grace Lee

Bad first dates? Too easy.

His name was Christian. First, he stiffed our waitress on tip. Then, when asked about the last time he was in a relationship, he said, “I’ve pretty much never been single since I was sixteen years old. Think of me like Tarzan swinging through the jungle – I never let go of one branch until I grab hold of another one.”

Horrified, I made an excuse to leave: “A friend is moving into a new apartment tonight and I promised to help.” It was obviously a lie – who moves apartments at 9pm on a Friday? I excused myself and escaped to my car, where I could safely text my friends and brief them on my ridiculous date.

Seconds later I heard a knock on my car. It was Christian, pressing his face into the window. I cracked it open half an inch, and he said, “Do you want any help moving?”


  1. What a clinger.
  2. He really couldn’t tell I was lying?
  3. Even if I liked him, I don’t introduce boys to my friends until we’ve been dating at least six weeks!

I shrieked, “HEE HEE NO THANKS” and peeled out of the parking spot. May or may not have run over his foot in the process.


Jordan Wang

Story #1

I once picked up a blind date from her house and said, “I heard about this really nice steakhouse right around the corner, so I got us reservations.”

She said, “I’m a vegetarian.”

Story #2

I was talking to my roommate in college about how I thought I should break up with my then girlfriend.  I didn’t know she was listening at the door.


Monica Stampfl

My worst first date was a date that ended before it really got started.  I can’t remember the guy’s name, I think it was Steve.  My co-worker had set us up on a blind date.  She had talked about what a nice guy he was, how he loved animals and trained his dogs, and how we had so much in common.  I had him pick me up at my house so my roommates could meet him and check him out. When the doorbell rang, I saw that he was pretty cute, dressed nice and drove a nice car.  I invited him in and tried to introduce him to my roommate’s dog, Rugby.  She was a dog who loved everyone and gave out kisses and snuggles freely.  When he walked into the living room, Rugby, a lab shepherd mix, ran out of the room, under the bed and started whimpering.  I told him that I was going to have to cancel the date because I couldn’t date anyone that my dog didn’t like.  He didn’t like that too much and left pretty upset.

Katy Lemon

We were second semester seniors, it was a first date and we went to a movie and the cashier asked us if we were under 12.  We were both short and looked young, but seriously, this was at night and we did look as though we were on a date.  I do not remember the rest of the evening, but it went downhill from there as you can imagine.  There was not a second date.  I did see him at our 20 year reunion and he made a special point to come up and tell me that he had grown.  His wife thought the whole thing was pretty stupid, as I recall.  She was bored (she did not go to our high school and did not know anyone) and went and sat in the car, I think.  Anyway, he asked me to dance which was nice because although he was taller, he was a nice height–shorter than my husband who is much too tall to dance with.  During our dance he told me that he had intended to ask me to the prom but after the disastrous date, he chickened out.  I said I was not surprised.  It took 20 years, but we ended our date on a happier note.  


Marisa Cozort

As a bright eyed 17 year old going off to college, my grandmother taught me to always get a date for Sunday night since no dinner was served in the dorms that night.

The first week of college, I passed time between classes by visiting the tables giving out freebies to sign up for clubs, credit cards and student activities. I had all the pens, frisbees and t-shirts a gal could ever want! I also got my first Sunday dinner date at the ROTC table (military folks on campus.) Captain, General, Lieutenant… I didn’t know what he was except in charge of the program and he had a car to take me off campus to dinner. After two dates, he asked me to marry him.  I finished my dinner, asked him to take me to a party where my friends were and hid under a table the rest of the night. Oh, and he was 25. He shipped out a few days later. A military wife I am not!