Awkward: I sold my teacher what?!!!

You may have already read this story on my other blog a few years back. But I wanted to breath new life into it and add some illustrations.

I sold my teacher what


It was around March or April of 1991. I was in 6th grade. I was 11 years old. I had the misfortune of having the same math teacher two years in a row. He wasn’t all that bad and still I wasn’t very fond of him. Maybe because Math was my least favorite subject and my grades were slipping that year.

(Look at that face of innocence! And also that sa-weeeeet outfit ;))

Middle School was the time when we learned what “going together” was all about (sorta). Kids were “going together” and breaking up every week. “Going together” more than 2 weeks was rare and nearly unheard of during these formative years. I myself had already had one other “going together” and breaking up experience so far that year. Now I found myself “going with” another boy. I don’t remember much about our “relationship”. I don’t remember how we got together or how we broke up…I only remember that it happened and was, in the scheme of things, quite an uneventful period of time in my life. The only mention of the “relationship” in my diary was short, cryptic and written 3 months after the fact.

(Names were erased to protect the privacy of those mentioned in my diary ;))
The spelling is literally killing me. 3 “mounths”, wow!

There’s probably more I don’t remember about this experience than what I do remember and I regret that I can’t provide you with all of the compelling details. All I know is that the halls had recently emptied, I’m guessing that the bell was about to ring for the start of class. My boyfriend was in the hall with me and before he left he gave me a quick peck. I’m fairly certain that this was the first time that had happened, yet it happened so quickly it almost seemed routine. I’m not even sure the kiss hit my lips although I know it had intended to.


Then he came walking up to me…my math teacher. Tall (in comparison to me), round, balding, and bearded he towered over me with his eyes narrowing at me through his round glasses. He informed me that he had just seen what had happened and would be calling my mother. I wanted to yell that he had kissed me and that I was the innocent victim of a hit and run (which was the truth), but I said nothing and walked with my head down, red-faced and embarrassed into class.


I don’t think my math teacher ever bothered calling my mother because she never talked to me about it, and believe me, she definitely would’ve talked to me about it. I suppose there was nothing to worry about, yet I still couldn’t help feeling embarrassed that my teacher thought me a naughty girl. In fact this very incident may have been what led to the ultimate demise of my “relationship” with Mr. Kiss-and-Run. I bet you’re thinking that this is rather a boring story and so far you’re right. Little did 11 year old me know the irony that awaited me 7 years later…


It was around September or October of 1998. I was 19 years old. I was working in the lingerie department of a very newly opened department store in the mall. Half of our department’s merchandise consisted of respectable sleepwear and robes, the other half of bras and panties and other foundations. Far from being Fredrick’s of Hollywood or even Victoria’s Secret we only carried a few racks of “special occasion” lingerie, otherwise known as…the sexy stuff.

(Me 1998, still the picture of innocence.)

Because the store had recently opened I was scheduled to work with several other cashiers, something that would be unheard of in the future as many resignations and lay-offs would occur. I was standing near the register talking with another girl when I happened to glance over towards the “special occasion” lingerie…
And then I saw him. Looking through the racks of sexy lingerie was my 5th-6th grade math teacher. He didn’t appear as tall since I was now (a little) taller than my 1991 counterpart, but he was still round (although perhaps more round), still balding (although more bald), still bearded (although more gray), and still wearing round glasses.


Before I had a chance to tell my co-worker and then flee from the scene…horror of all horrors he came walking up to the cash register. Suddenly I found myself alone. Where did my co-worker go so quickly?! I took my long hair and threw it in front of my face to hide my features and turned my name badge around to hide my name. I was hoping he would quickly purchase a nice tasteful negligee for his wife (?) without recognizing me. Well, he didn’t recognize me…at least he didn’t acknowledge that he recognized me. In fact I’m not sure he even looked directly at me as I’m sure he may have been quite embarrassed of himself.

Embarrassed because, no…he was not in fact buying a nice tasteful negligee. Instead I found myself ringing up a pair of crotchless panties…in size 2XL…for my 6th grade math teacher! (*shudder*)
Paying with a credit card confirmed my suspicions that it was indeed him. Aside from me mumbling the purchase total I’m quite sure that neither of us spoke during the whole transaction including any hellos or goodbyes.


He left and I pulled my hair back out of my face which was much redder than it had been 7 years ago in the hallway at school. Once I had a moment to recover from the horror of what had just happened, a smile broke across my face and I found myself wishing that I had his mother’s phone number…that naughty, naughty boy!


Do you have an awkward story to share?
Let me know in the comments!

This was linked to Mama’s Kat Writer’s Workshop for the prompt:
1.) Describe a time you made things…awkward.

Related Posts:
*Dear Diary: I’m kind of a stalker

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About Jenn Rian

Jenn Rian is a mom, blogger, actress, yoga instructor, and cosplayer. She blogs about as often as she showers, which isn't very often. Author of and (

Posted on June 6, 2013, in About Me, Awkward, Humor, Kinda Sketchy, Old School, True Stories, Undergutchies, Writer's Workshop and tagged , , . Bookmark the permalink. 50 Comments.

  1. LOL, now there is a GREAT story! Thanks for the chuckles!


  2. You know what I’m thinking? Those were probably for HIM!!! LOL. It’s possible that your math teacher was sporting a little sump’in sump’in under his khakis while you were still in his class. Uh oh…did I just make it more awkward? LOL


    • Don’t think that didn’t cross my mind…I need to bleach my brain 😉
      And yes…you just made it more awkward…

      🙂 Thanks for visiting!


  3. Your illustrations are marvelous! And I, too, kind of wondered if the panties were for him. Ewwww.


    • Thanks, Dyanne! I had to keep reminding myself to keep it simple, I stink at Pictionary 😉
      Gah, I’m not sure whether or not that’s creepier than the alternative, blech.


  4. I WISH he had heard you say that. The illustration of the panties is outstanding.


    • Oh my gosh, I would’ve died!!! I don’t really get embarrassed but that situation was just a little too creepy for me.
      Thank you. I spent a ridiculous amount of time around panties 😉


  5. That is hilarious. I would have died. Your math teacher was much like mine in Jr High, rather round, always wore a blue shirt and was very annoying.


    • 🙂 I can laugh about it now but it was definitely so awkward then. I probably wouldn’t have batted an eye if it had been a female teacher, but honestly any male presence in the lingerie dept would put us all on edge! This was just too much! 😉


  6. This post was great! I am still smiling. I am quite sure I would have been horrified at 19 and to sell one of my old teachers something so…………. no word comes to mind but gross. lol. Wonderful drawings. I wish I had kept my diaries from middle school. It would be great to read them now. Loved your hair in the photo. Great curls……… coming from someone with naturally curly/frizzy hair!


    • Seriously, it was so weird. Honestly it was awkward selling anyone crotchless panties, but your male 6th grade math teacher? Kill. Me. Now. 😉

      I’m finding a lot of people saying they didn’t keep their diaries. I couldn’t imagine. I save everything. In fact one of my diary entries mentions a boy giving me chocolate for Valentine’s day…and I still have one of the candy wrappers! I’m a freaking hoarder!!! You should check out my other diary story here: Dear Diary: I’m kind of a stalker

      It looks great, right? My hair actually refuses to hold a curl because it is so ridiculously thick. In that photo I had just removed my hair from an “up-do” because I had went to a formal dance. I told my boyfriend, “My hair looks amazing…take a picture!” 10 minutes later it was a hot mess 😉


  7. LOVE IT! But it’s HIM who should’ve felt awkward, not YOU. You should’ve pulled your hair back and smiled big at him and said, “Hi, Mr. XXX. Have special plans this evening?” Watch that big bald head turn beet red. 🙂


  8. That is absolutely mortifying! I grew up in the same town my whole life and now reading this I’m soooo glad I moved away. I just couldn’t deal with seeing any of my beloved teachers buying unmentionables!


    • …and I still live here one block from the house I grew up in. In fact that very block housed 3 different teachers of mine (luckily they were nice and normal and never purchased naughty underwear from me!).


  9. Hahahaha! I love it! Crotchless panties!


    • I know, right? 😉
      Random Fact: The actual crotchless panties that he purchased were black, but it was too difficult to see in the illustration, so I made them red instead.


  10. What a fantastic story!!! I love it. I was cracking up. I can’t even imagine. Great share. Thanks for stopping by and taking the time to read and comment. Glad I came by. I needed a great giggle.


  11. This is so awesome! I understand the awkward-ness of it, but I like that there’s a twist of karma in there, too 🙂


    • I know, I do enjoy that part 🙂 I wish that it wasn’t all so creepy so that I could’ve just “owned” it and maybe embarrassed him a little. But I didn’t want to welcome any strange comments, so…


  12. That is so fabulously awful, it’s hysterical!


  13. So funny! Thanks for the morning laugh 🙂

    I would like to think that my teenage self would have said something witty and snarky to him, but I know that I would have done the same as you and been mortified ~ hiding behind my hair.


    • When you find out your former teacher is kinda creepy you just don’t want to take the chance that he may get even more creepy with you. So you hide 😉


  14. So funny! I have to admit that I was wondering if he was buying them for himself…which is even more awkwardly EWWW!


  15. Ahahahahahahaha!!!!! This is the funniest thing ever! I can’t believe this actually happened for real! Sounds like a comedy show episode! Aw man. Thanks for the laugh. 😉


  16. Jenn, I love the drawing of the crotchless panties. Your art really makes it all come to life. You are right that there is no way you could make up something as awkward as that. Thanks for sharing.


  17. So, so awkward! That story was so funny. I would have disguised myself, too. How embarrassing for him… if he only knew! Crotch-less panties!! BTW, your drawings were perfect!

    Thanks for visiting my blog. Leslie (another commenter) made a nice comment to your comment… you can go back to read.


    • I really thought having a visual would bring the entire awkward story to life 😉

      Thanks so much for letting me know, Carol, I’ve revisited and commented 🙂


  18. Totally awkward! I would have felt just like you at the time. Your math teacher sounds so nasty. How embarrassing for him! You do have the last laugh. But… I wouldn’t like to think about it too much. eeewwww! Thanks for the good laugh today.


  19. 31millionseconds

    That is hilarious! Do you think they were for him or was his wife rather, ahem, large?


  20. Hilarious! This whole story was great. I love the picture of you in 6th grade. We’re the same age (yay) and I totally had those same overalls (or pretty close) and I wore them all the time!! Have to love those early 90s styles. Love your illustrations. 🙂


    • Thanks, Kara! In 7th grade I had a big thing for “bibs” (that’s what we called overalls) and we would always wear one strap hanging down…because that was cool (?)! Mine never looked as cool as they were supposed to.

      I was born in September ’79 so I was actually about 11.5 when this happened 😉


  21. Haha How ironic! At least yours wasn’t your doing. Every teacher has a secret right? Love your illustrations btw.


  22. That is hilarious. I worked at the mall when I was in high school but I never remember my teachers coming into the store to shop.


  23. BWAHAHAHAHA! That is pure gold! I have never had anything happen to me like that!


  24. Oh, my – so funny! I don’t think I can touch this story for overall awesome awkwardness.


    • Seriously, I still can’t believe that it happened. Sometimes I just want to go on Facebook and actually use his name and tell my school friends, “Ew, guess what Mr. Math Teacher did!” in hopes they may have horror stories of their own!


  25. This makes the illustration in VBAC to the Future that much more funny! This is Sparta, over & out.


    • Right? I was just going to include the picture of him at first and then I thought, no I definitely have to add the panties, even if no one picks up on the reference!
      P.S. SPARTA RULES!!!


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