27 Of My Most Cringeworthy Moments From My Early Twenties I Will Recount Here For Your Entertainment

If you are my mother or my father or are in any way affiliated with them, please stop reading right here. Unless you’re Aunt Julie. Because you can hang, Jules.

James Garcia
James Garcia

1. I once locked myself into a bathroom with several cases of beer, because the cops showed up to a college party. I declared it my throne and proceeded to continue to drink cans of Coors Light for over an hour BY MYSELF until I decided it was safe to emerge.

2. After my 21st birthday party, I fell asleep on my staircase with my tights midway down my legs cradling my then baby dog and assuring her over and over, “You’re so beautiful.” I woke up to her chewing on my hair.

3. I played Peter Pan in college and had some sort of weird virus that resulted in 85% of my body being covered in hives. I was released from the ER after my school’s health center sent me there post thinking I was going into anaphylactic shock, but I had to do press and several photo shoots for the show. So now, there are photos of me (that yes, you can find) dressed as Peter Pan, flying around, while on several milligrams of Valium. Gives a whole new meaning to “flying high.” (sorry I had to.)

4. Once I got drunk in a field solely so I could hang out with a goat named Penelope. Here’s a picture:

Also had an angled bob and a nose piercing. It was a LOOK.
Also had an angled bob and a nose piercing. It was a LOOK.

5. My boyfriend for the latter half of my early twenties was around a year younger than me. So he couldn’t drink with me (in public anyway) at my 22nd and instead had to take care of me, bless his heart. On my 21st birthday a friend had challenged me to take a shot of SUPER cheap whiskey and I’d managed to do it. On my 22nd I tried to complete that same challenge and ended up puking into a cloth napkin, and sneakily throwing it away in the trash. My boyfriend promptly took me home after.

6. Another throw up story (let’s just stick with the theme) involved a pint glass. A party was being thrown at my ex’s house and naturally, I didn’t want to attend. One of my best guyfriend’s offered to accompany me to a bar near said ex’s place called “The Town And Country Lounge” which is a bar in a refurbished double wide. We sat there for approximately two to three hours, drinking cheap beer and shooting whiskey. The last shot of Jameson I did didn’t sit well, and I ended up methodically vomitting into the pint glass next to me, filling it straight to the brim. Surprisingly though, I didn’t spill.

7. At 25 I got so heated with a cab driver after a long night that he ended up calling the police on me. From my own phone. Saving that whole story for my eventual Lifetime movie. But it happened.

8. I went to a One Direction concert and a stranger who was drunk and talking animatedly with his hands clocked me straight in the face. I told him it was okay, I missed Zayn too. Again here’s a photo from said evening:

We definitely know, oh oh oh, we know that we're beautiful.
We definitely know, oh oh oh, we know that we’re beautiful.

9. At 25 I sent presents to some dude who wrote for the same website as me, because I thought it meant we’d be friends. Now I’m pretty sure he just wanted to have phone sex (never did) because he was lonely as he stopped talking to me the SECOND there was a possibility of us hanging out IRL. Learn from my mistakes kids: don’t send flat-brims to people just because they’re sad. Save that money.

10. I left my number on more coasters and napkins for cute bartenders than I can even remember. It’s not really a cute move though, and I fully shake my head at myself now.

11. I sort of notoriously trolled a guy on Tinder and wrote about it. It made a lot of people really mad. I still stand by my original intent of writing the piece, which was/is that it’s kind of fucked up that we laugh when people threaten us or harass us or even just get rude, but I didn’t execute this well at all. Like honestly, I am linking to it and saying, “I think this is poorly written and I am the one who wrote it.” BUT – I don’t believe in deleting work even when I don’t really relate to it anymore or even when it doesn’t garner the reaction I was hoping for. Instead I just shake my head when I get random messages about this piece (yes, even over a year later) and use it as a reminder to always do better.

12. After my first big breakup I decided to get out of a dodge for a bit and flew home to be with my parents and my childhood best friends. Only problem, I was flying out of my college town on my ex’s birthday. And apparently, his parents were also flying out on the same flight to go on vacation. I was in first class (not bougie – just the only ticket that was available) and they had to awkwardly stand beside me waiting to get to their seats. One of my absolute least favorite memories.

13. I impulsively got a tattoo with a sort of boyfriend one day on my ribs. I didn’t really WANT a rib tattoo but this dude told me it was “so sexy” so I caved. I also made the mistake of not going to a reputable artist, and frankly the tattoo looks like shit now. Eventually I’ll get it covered up but for now, the scratchy Alice in Wonderland quote stays. Here’s another a picture so you can see visual representation of my mistakes!! Yay!


14. Once I went out on a date with a guy who actually, seriously quoted that fucking AWFUL book about picking up women called The Game and I didn’t leave. Not only did I not leave, but I let him stay the night at my apartment (didn’t hook up with him because I maintained SOME level of self-respect) AND let him shower in the morning. He used my brand new, pretty spendy Sephora bubble bath as body wash, and opened brand new shampoo. He wanted to have a “discussion” after I told him I wasn’t interested in seeing him again. Yeah…I pick winners.

15. For my 20th birthday party I threw a joint birthday party with my friend Nicki that was “P” themed. This meant everyone who came to the party had to come dressed as something that started with the letter P. (Best costume was this dude Kyle who came as the preamble. It was gold.) The only other rule was that no one could come as a princess because that’s what Nicki and I were being. I dressed like this:

seriously how did i have a boyfriend then but I'm single AF now
seriously how did i have a boyfriend then but I’m single AF now

16. I was so in love with a boy that I bought him Decemberists tickets for literally no reason. Actually, come to think of it, a lot of the moments where I look at my younger self and go, “What the actual fuck were you thinking?!” have to do with spending money on boys who didn’t appreciate me. My therapist told me that I show affection through material goods because I have difficulty expressing emotions. Whatever, I’m working on it.

17. I have written so many prose pieces about guys who I knew were pulling away from me in a sad, pathetic attempt to try and make them see that I was worth their time and attention. Spoiler alert: If a guy doesn’t even read your stuff to begin with, this will literally never work.

18. At 23 I went to Las Vegas for my best friend’s 21st birthday and the two of us go so lit up before going to the wax museum that we found a karaoke machine (it’s next to the was figure of Simon Cowell) and started serenading the entire museum with renditions of Celine Dion hits like “Taking Chances” and “The Power of Love.” We attempted to shake his hand after. We cleared the room of 70+ people. What I’m saying is, it was embarrassing.

19. I was really bad about remembering to renew my tags for my car in college and was pulled over for said offense one summer, and still didn’t renew my tags. 7 months (yes I know, I was/am the worst) later I was pulled over AGAIN for the same thing. Apparently there was a warrant out for my arrest and the officer decided midnight was the appropriate time to lecture me about this. Catch? I had just finished a performance of The Mikado which, if you’re not familiar, is set in Japan. So I was in FULL kabuki makeup while this policeman decided to lecture me about my fuck up. I was sobbing, Ben Nye makeup was smearing everywhere, he felt pretty bad. It was overall just a mess. But I didn’t go to jail. Thanks, Missoula Cop who didn’t take me in while I was still rocking the geisha makeup. I really appreciate it.

20. I was feeling vulnerable and sad one Halloween and decided the cure to this was hooking up with my friend’s much younger, VERY hot, trying to be a stripper friend. It was fine, it was whatever. But we hooked up on the floor of an apartment which was basically concrete. I ended up slipping a disc, bruising my tailbone, and having to spend the next 3 months getting chiropractic work to make my back okay again. He was hot, but not hot enough to justify that amount of back pain. #srynotsry

21. I got violently ill once from antibiotics and promptly shit in my leggings after trusting the fart. There is more to the story but again, saving it for my future bestseller.

22. I thought this was a good look. And also did this in public.

yep. that's me. form a line, gents.
yep. that’s me. form a line, gents.

23. In college I played Columbia in the live musical version of The Rocky Horror Picture Show where, for the midnight shows only, we were topless. I debated about it, but it was a paid gig and I felt fine about it so I decided sure, why not. My boyfriend at the time was NOT okay with it. I later found out he adamantly REFUSED to let his friends come to the show, even going so far as to pay them back for the tickets they had already purchased. I didn’t find this out for years and it still makes me super embarrassed for his behavior.

24. A guy broke up with me when I was 25 because I didn’t make enough eye contact. That was his honest to god reason. (Still bitter.)

25. I went on a mini vacation with some friends to Austin, Texas for my 26th birthday and decided to really just GO for it when I was there. This meant doing one of the ultimate “why not” moments: the Tinder one night stand. Only problem? We didn’t know our way around Texas and I didn’t bring any condoms. So my solution was to have Postmates deliver them. I didn’t even try to play it off and ordered like, chips and gum to make it better. I straight up just ordered a box of 16 Trojan’s to the AirBnb. The delivery man was loling, my “date” was loling, my friends were loling. It was lols all around. 10/10 recommend.

26. A friend of mine came to Seattle for an audition and I took her out one night to blow off some steam/show her the city. We ended up drinking all night with a professional indoor soccer team from Vegas, and I definitely got naked in a photobooth with a bunch of them. Somehow though, I still didn’t get laid. Only I could be one of two girls surrounded by a bunch of guys who were hot, professional athletes, show them all of my tattoos that required me taking my clothes off, and end up going home to eat queso in bed.

27. I lived. I made memories. Or I had those memories told back to me because I didn’t really…well…remember them. And even though sometimes that makes me all “god dammit smdh” I honestly think it’s pretty dope that I have all of these stories – cringeworthy or what have you.

Plus I once peed on my neighbor’s lawn furniture because she was threatening to call the cops on my Harry Potter themed party. And you can’t pay money for those kinds of stories. Thought Catalog Logo Mark

About the author

Kendra Syrdal


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