Adventures in Dating: Vignettes from Dates Gone Wrong

Written by Heather Waldorf & Laura Pedemonti

Edited by Kathleen Morris & Tara Sanders

Three brave women came forward to tell us about their hilarious dating mishaps, misunderstandings, and misadventures. The great thing is that we can (almost) all relate to them and laugh with them about it now. This is all in good jest, so we hope you have fun reading them!

Story #1: The Ride of My Life and "The Allergy"

Fact: On a first date, one should refrain from bathroom talk.

Many years ago, I used Match.com, right when it first came out, before it was actually a reputable thing.  I'm pretty sure their filter system could have used a few more tweaks to it.

A certain young man and I discovered we were a “match” and chatted back and forth via email for about a week before deciding to meet for dinner. Since he only lived about 45 minutes from me, we figured, “Why waste time on email?”  Looking back, “wasting” a little more time might have actually been a good thing and could have spared me a great deal of embarrassment.


When he picked me up, I was pleasantly surprised by his “easy on the eyes” appearance.  My mind did not have long to wonder about why he was still single.  Within 5 minutes of being in the car with him, I knew.  His driving. Not kidding. For some reason, he found it necessary to make eye contact with me as he proceeded to ask me about 50 questions while driving in a straight line down a curvy road during rush hour traffic. I am pretty sure my life flashed before my eyes a few times and I screamed "Dear Jesus!" at least a dozen times. Luckily, the restaurant he chose was only five minutes from my apartment, or I am sure I would have actually met Jesus that night.

As the night went on, I came to fully understand why he was still single (and his driving was only a small part of it). Before we even ordered our dinners, he was mouthing off very rudely to the waitress. As she walked away, he continued to make fun of her. I was cringing on the inside hoping no one around heard him because he was loud.

At that time, I was not much of a drinker, even socially, but that night it was clear that a huge glass of sangria was necessary.  When he offered to order something, I very eagerly accepted. After we ordered dinner, he excused himself to go to the bathroom. I think, no joke, he was gone for ten minutes. I ordered a second glass of sangria and started eating my dinner, praying that maybe I was not what he was looking for and he had left.  Maybe I was going to have a nice night alone! But no, he eventually returned. After he sat down, he apologized and proceeded to tell me he was lactose intolerant and something he had eaten caused some “potty problems.” He proceeded to talk, in detail, about his experience. I must have been five shades of red and was totally ready to throw up my bang bang shrimp.

The evening did not improve.  He was, of course, unhappy with his meal and made a big stink about it, totally embarrassing the waitress and me. I’m not sure if it's because my memory was trying to forget about this night or if I had too much to drink, but I think I ordered a third glass of sangria as dessert – but only because I knew I had a terrifying five-minute drive back to my apartment and thought taking the edge off with another drink was my key to survival.

Obviously, I lived to tell this story. And I'm glad that online dating sites have since become a reputable way of meeting someone; however, that night I decided, as I disabled my match.com account, that I would simply stick to the old-fashioned way of meeting men – getting set up! At least then I could have someone else to blame if it turned out bad! This experience? Well, this experience was totally my doing.

~Heather

Story #2: Dinner and a Tournament (of Sorts)

Fact: Italians take their food (and dating) very seriously

I dated this guy several years back.  One night, he asked me over to his house for dinner.  While I definitely thought it was a wee premature to invite me, practically a stranger, into his house for our third date, I knew he was harmless.  Well, kind of…

Let me just start off by telling you that, as an Italian with two parents who are very competent cooks, the only jarred sauce we ever had was sauce they’d made (and jarred) themselves with tomatoes from their organic garden.  And if the jar did have a label, it was a homemade, masking tape one that said something like “Marinara - July 1999."

Full disclosure: my expectations were definitely high going into the dinner.  

As I watched him "make" dinner, my heart sank a little bit when I noticed he was making me pasta….with jarred sauce…that had a label. He said he "made" me garlic bread, but it turned out to be bread from a foil bag that had been under UV lights at a grocery store all day. Ugh! (Take note, my non-Italian friends, this is indeed not garlic bread. And even if the bag says “Garlic Bread,” be warned, it’s not what it professes! It’s more like oily dough with green, fake parsley flecks and burnt, granulated garlic-like grit.)  Next was bottled Italian dressing on a salad that came in a bag. And honestly, this would not have been an offensive meal (to a red-blooded Italian) had he just said that he didn’t really MAKE anything but rather "arranged" everything. Needless to say, it was an awkward dinner at best. But something in me kept wanting to give him the benefit of the doubt, though; I may have been wrong.

After he cleaned up from dinner, he told me to go into his living room.  He said he'd be right back.  I had no idea what he was doing until I saw him come out of the basement.  He was wearing a brown Jedi cape.  He was holding two light sabers which were full length and fully working. Specifically, the kind that makes the laser sounds when you swing them.  One was for me.  He told me to get up and duel with him.  “Duel with him?” I thought as I scanned the room to find my coat in an effort to miss our first (and what would be our last) Star Wars fencing tournament.  I swore I left my body. My mind tried to understand how I (of ALL of the 7.442 billion people in our non-fantasy world) was literally getting off the couch to take the saber.  I held on tight, and I waved it.  That’s what people do when they hold those things, right?  Had I known he would see this as a mating call of sorts, I would have kept it still and could have also avoided his return swing which left me with a bruise on my right upper thigh.  

I’m not exactly certain of the events that happened next.  I think he actually wanted a kiss?  This was a while ago, and I know the mind tries to forget nights like this one.  But I’m pretty sure I was so flustered that I neglected to thank him for the fake Italian night and for the once in a lifetime chance to cut air with someone.  I’m also pretty sure we went out another time (I mean, someone can’t ALWAYS be THAT weird, can they?), but it just got worse.  Fearing that I would one day have to name my child “Hans” or “Leia,” I decided it was best to use my force and put an end to something that would never, ever be.  

~Laura

Story #3: A Very Unfortunate Event

Fact: A date can go wrong, but still end in matrimony.

It was date night with my (unbeknownst to me at the time) future husband. We had been officially dating for about 6 months, and I was still a bit reserved around him because I was pretty young and new to the whole dating thing. Aunt Flo happened to be in town, and I hadn't had the opportunity to “freshen up” all day at work. The only backup I had came out of its wrapper in my bag, and I thought surely my insides will not appreciate this ratty piece of pen-stained cotton. With no replacement to work with, I had kept in what I was wearing all day long, not unlike a high stakes gambler. 


My beau and I worked together and had an early staff Christmas party at a nice restaurant to start the night. I instinctually (read: I’d done this before) made a makeshift pad to prevent further leakage. You’re hoping that something embarrassing happened there at the holiday party, aren’t you? Well, it didn't, but I needed to get that thing out FAST, or it was going to do it all by itself. My dilemma was that, after dinner, we were going back to his place before we left again for our actual date. (His place being a house full of men.) 

“Hey,” I said as we stood outside waiting for our car, “I need to go to the bathroom again before we leave the restaurant.”

“Why’s that?” he asked. “We're two minutes from my house and the valet driver is about to pull up.”

So I caved, embarrassed to make it seem too urgent, and decided I'd remove the product at his place - with no replacement, mind you, but I am not above wadding up TP to create a temporary solution. I knew, however, that I only had two options for disposing of the used item, and neither were going to work for me. 


Option # 1: Dispose of it, wrapped tightly and neatly, in the [empty] bathroom trashcan shared by two guys. Problem: they had a dog in the house plus cream colored carpets. Dogs love digging through the trash. Also, what bachelor regularly changes out the powder room wastebasket? 

Option # 2: Flush it. Problem: I have lingering trauma from living in a century-old house full of girls who naively flushed their feminine products and created horrific plumbing backup in our house (and consequently, the house full of jocks next door). We are talking MAJOR issues and I will spare you the details. My boyfriend’s house, too, was older and I didn’t know a thing about their plumbing situation. So, do I really need to explain? All I needed was to picture the face of a repulsed college boy discovering a wad of flushed tampons in his yard (that the annoyed plumber had thrown there) and place it on my suitor and his 30-something professional roommate.  

What was I to do? Thinking on my feet in a stark white bathroom merely yards away from the man with whom I was falling in love, my third and only option was to find a fast, clean way to store it temporarily. So, I wrapped the item up extra tight, placed it in the tupperware that I used for lunch that day, and stuck it in my bag and carried it around for the rest of our romantic date. What he didn’t know didn’t hurt him, and I wooed him with my charm and crisis-averting wit instead of scarring him with a plumbing fiasco.  

With several years of marriage now under our belt, I’m confident to say that I’m partnered with a man who would have said yes to me no matter what the disaster had been.

~Anonymous

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