Worst date ever contest: Entry #1

Hi, friends. Did you wake up this morning with a post-holiday weekend case of the Mondays? Do your pants no longer fit after four days of carbo-loading? Are you still recovering from the trauma of attending your 10 year high school reunion? Or is that just me and L?

romy and michele

Never fear. We’ve got the cure here at Stucu, and that cure is other people’s misery. Schadenfreude FTW!

We LOVED reading your submissions to our ‘worst date ever’ contest: between the picture fraud, money drama, tooth issues, sexual harassment and general soul crushing awkwardness you shared, the three of us are (for once) feeling like our dating lives are not the bleakest on the planet. And for that, dear readers, we will be eternally grateful.

We’ve picked five worst date tales to share with you. We’ll post one story each day this week for your enjoyment, and on Friday when we post the last story you’ll be able to vote for your favorite. The three winners will receive some swanky Stucu swag (say that five times fast–dare you) but more importantly, the honor and glory of being pitied most grievously by their internet peers. Thanks to all who participated and happy reading!

Entry #1—Dental Drama

So when we say “worst date ever” contest, the original interpretation is quite obvious, but how about “worst date ever” when you are in fact the culprit?  Let us begin.

Years ago I went on my first date with my now husband. We went figure skating and out to a pizza place I had never tried. To provide some very important and oh-so-embarrassing context, I have tooth implants. I have two fake teeth right up front in my mouth, and at that time, I was wearing one of those Invisalign retainers with two fake teeth in them. This retainer was quite old, and if you think food didn’t get stuck between the plastic and the fake teeth, think again. This led to some pretty unique food filled smiles (I could literally write a book).

So post pizza, my nerves high and wondering if there would be a kiss, I did what any toothless gal would do and waited for my date to become preoccupied.  When he was searching around for the waiter to ask for the check (we split, #firstdatedebate), I pulled out my teeth to do an inspection. My gut was right: pasta sauce and cheese had manifested itself in my retainer in front of my teeth.  Again, thinking my date was preoccupied, I did what at the time seemed logical (missing teeth = missing part of one’s brain), and started swirling my retainer around in a glass of water on the table like it was a god damn dishwasher.

The horror and curiosity on my date’s face was unparalleled. I knew I had absolutely blown it.  It’s hard to really laugh at the whole “pulled out my dentures to clean them at the table while in a restaurant” routine, so the check came and we headed out. I was mortified at my own dental date behavior and thought that was it.  My crush that I was obsessing over for 6 months was going to walk away. But obviously, since I’ve mentioned him as my husband, this story ends well. The true moral of the story here is: go to the bathroom to deal with your teeth issues, girls!

Message Monday: Unsolved Mystery

Hey there, loyal readers. Just a heads up, LSD are busy ladies at the moment. Between moving, vacays, bridal showers and bdays, we may be a bit light on posts this week. Thanks for your patience 🙂 (L, I know how much you appreciated that emoticon).

Anyway, happy Message Monday! This one hits close to home for me–literally.

message monday ht

The part of the message that I blacked out? You guessed it: my high school.

Running into someone you know on okcupid is a very real fear of mine, much like being murdered by a date and becoming the subject of a Lifetime movie. You put your profile out there, and sure it’s “anonymous”, but your picture is still attached to it. And it’s the f-cking internet; nothing is really anonymous (except, we hope, this blog!). So yes, sometimes I worry that my boss could stumble upon my profile and read the sex questions I answered. Or a co-worker. Or a family member. Or a crush or hook up from back in the day. Basically anyone I’ve met, ever. Because of this fear, the number of questions about sex (there are hundreds) that I’ve actually answered basically amount to:

liz lemon treat

Also at the top of this list: former classmates. And don’t worry, this isn’t the first time this has happened to me, or even the second. TWICE before I’ve run into dudes I went to high school with, I guess hardly surprising given the fact that my hometown is less than 10 miles outside of Philly. L and I went to a pretty small high school, though; I believe our graduating class was 175-ish people. We literally know every single person in our class and in the classes 1-2 grades below and above. So I honestly wasn’t expecting to have to play the ‘who the eff is that?’ game until this fall at my (drumroll please) ten year reunion. (F-ck, I’m old). And I figured at least then I’d be with my friends, we’d be drunk, and possibly decide to perform an impromptu interpretive dance:

So when this dude messaged me and I didn’t recognize him at all, I figured I was just having a brain fart and that my friends would ID him immediately. I sent out the appropriate mass text with that screen cap, plus his full profile picture which it’s worth noting is a legitimate head shot/glamour shot (which you may recall is on my list of profile pic no no’s from back in the day). 

ht head shot

Can’t say it any better than my friend did:


Anyway, no one had ANY IDEA who this terrifying 29 year old bisexual claiming to be our classmate was. So I responded to him, curious now about this mystery:

ht convo

Ummm okay.

1. ‘We probably never crossed paths in school’–Creepy, slash you’re obviously right since I have NO IDEA who you are.

2, ‘You clearly appear to be the best looking’

donna excuse me

Hey, asshole. First of all, that’s not even true. My friends are mad cute. And since you claim to have such a stellar memory, they were also adorable in high school, even though we all had slightly more questionable fashion sense back then.


Second, based on your picture I would bet that you’re probably on a registered sex offenders list somewhere, so I’m not really sure you’re in the position to judge anyone on their looks. Third, do you think that I’m actually pathetic enough to fall for this blatantly disingenuous, totally lame attempt at flattery? Oh gee, a creepy stranger on okcupid claiming to know me from 10 years ago insulted my friends, but he thinks I’m cute! BE STILL MY HEART.


I was officially grossed out by this mystery acquaintance, but now it was basically my mission in life to figure out who he was. I was this close to making my mom go into our attic, find one of my yearbooks and flip through the entire class of 2002 over the phone with me, but I figured I’d save her that trip if I could and check with some other friends from high school first (you’re welcome, mom).

I saw some of those friends on Saturday night, and the search continued. We named every kid we could think of with that first name, but nothing checked out. We texted another friend who lives in NYC and put her on the task force. She thought she had a guess, but then someone actually did consult a yearbook upon returning home and ruled it out:


So as of Monday, July 29th at 12:30 pm, the case of the creepy classmate remains open. If anyone from my high school has any leads, they can leave an anonymous tip in the comments section. We’ll see you next time on…