Chronicling my mis-dates isn’t something I’ve aspired to do in my adult life. It just happened because I’m single and I date — a lot — in the city of New York. And over the course of a few years, eventually I’ve found myself baffled by all the buffoonery; indignant at the fact that all these unbelievably ludicrous things occur, particularly on what are supposed to be romantic rendezvous.

That’s right, I’m the keeper of The Bad Date Files: a document housed on my MacBook in which I chronicle exactly that — very bad dates. But, while some girls might return from a night out complaining about how they were (gasp!) asked to split the bill, they have nothing on me. I like to think that the egregious behavior of a few of these men will go down in infamy.

Following are 10 highlights. Maybe you can commiserate (but hopefully not.) Regardless, these files are a constant source of entertainment and delight for me, so let’s share the wealth, shall we? Here goes:

The Conspiracy Theorist

Testing the chemistry between two friends isn’t always easy, but we were giving it a try. We’d been flirting openly amid our group of friends, and this evening it was finally going to be just us and a movie, at his place. Make-out time, right? Wrong. Wrong because he opted to pop in a documentary about 9/11 conspiracy theories. The date ended in the following manner:

Him: “I can’t believe you’re not grasping this! Don’t you understand? AMERICA IS A COUNTRY FULL OF P*SSIES!!”
Me: (crickets)
Him: (voice much softer now) “Oh, no. Did I just ruin the mood?”


The Drug Dealer

After being picked up by this extremely attractive, charming (wait, did he just call me “baby girl?”) gentleman at Rite Aid and storing his number in my phone as Drug Store Guy (foreshadowing!), we set up a time to meet at a local lounge. The bubble burst five minutes into our first date, when he told me, quietly, that he “hustles” for a living. I wasn’t sure I fully understood what that meant — I don’t even smoke pot — but I kept on gamely sipping my cocktail. Until he proceeded to excuse himself numerous times to go outside and “work,” then paid the check with a huge wad of cash that he threw on the bar and didn’t even bother to count. (I know, at least he paid it.) Apologies to my pot-smoking friends who would have appreciated the hook-up.

Prince Charming–Turned-Cad

This guy joined a friend and me on a double date at my friend’s beach house. The first night we went out, he literally saved a man’s life, holding an elderly stroke victim upright to help him avoid a concussion. I watched this take place while filled with amazement and wonder, hyper-aware of the “Dreamweaver” song I was hearing on loop in my head. The next night at a local bar, he got into an argument with a girl who was rude to him while walking by. Not great, but people are rude; it happens. Well, this argument culminated with my Prince Charming actually slapping this girl in the face! To make matters worse, I find out later that he had slapped a bachelorette — at her own bachelorette party. So much for gallant.

Dirtbag in Disguise

After dating an unbelievable line up of degenerates, liars and losers, I’d decided to play it safe and date someone I’d known a long time. Someone with that nostalgia-inducing (OK, actually ridiculous) mushroom haircut, someone who was a middle-school math teacher. On Long Island. I was convinced he had all the makings of the ever-elusive nice guy. But as it turned out, I’d been grossly misled. After having gone out on one lovely L.I.-based date, Mr. Nice Guy came into NYC on a Saturday evening, hit on my roommate and one of my best friends, crashed at my apartment in my bed but didn’t even make out with me, “borrowed” from me a movie and my most favorite, treasured rock album ever, kept both, then moved to Virginia — all without ever talking to me again.

The Guy With a Girlfriend

We made plans to meet up after having not spoken in years. We opted for a candle-lit wine bar. We talked, flirtatiously, for almost three hours. He bought me my drinks. As we were leaving, he mentioned that his girlfriend had a similar shirt. Yep, his girlfriend. Attention, boys: Your being coupled up is information you should share early on in conversation, especially if the conversation is taking place in a date-like setting, with date-like occurrences taking place. Thanks! 

The Religious Zealot

We’d spent a lovely, rainy evening in, drinking boxed wine at my apartment. Everything was grand — he was handsome; the conversation was intelligent and thoughtful. There was palpable chemistry. Chemistry that combusted the moment he asked me, “Do you accept the Lord Jesus Christ as your savior? I remember looking at my glass of box-bred wine and thinking, God (no pun intended), I wish someone were filming this right now

The Accidental Exhibitionist

After a night out with a very cute guy, I went back to his place that he shared with a truly raucous group of guy friends. I vividly recall noticing a penis that had been drawn with a Sharpie on a kitchen appliance, and an entire room — an entire room, people — devoted to empty beer cans. Needless to say, I stayed over and things got pretty steamy in his room overnight. In the morning, I stood up to get dressed, and heard someone cough. I glanced at my date; he was sound asleep. I looked across the room. There he was, the source of the coughing. It was one of the dude’s friends, sitting up on the couch in the same room as us, where he then proceeded to tell me he’d been — all night long. 

The Potty Mouth

All my friends know that I hate bathroom talk. There’s nothing that turns me off more, which is why one particularly button-pushing ex once sent a chocolate cake to my office on my birthday with the words “Happy Poop Day!” written in pink frosting. (Stories about that guy live in another file entirely.) Anyway, while on a date with a guy I’d had a thing for since college, it became clear that he did not share my distaste for all things scatological. On the contrary, this dude had nothing to talk about that wasn’t utterly disgusting. In fact, he spoke so loudly about farting, barfing and sh**ting all through our meal that I couldn’t work up an appetite for my food, let alone Date Two. 

The Undercover Professor

I met this one online. After several days of texting and online messaging, we planned a date. Well, rather, he planned a date. And, I thought — at least initially — that he’d planned it well. He took me to an obscure Japanese restaurant where there was no English on the menu. He ordered my beer for me (a minor offense, given I hadn’t really wanted a Sapporo, but I drank it). He also ordered food to share (in Japanese, the show-off) without asking my opinion about what I might want. The food came, and we indulged in some truly bizarre fare: The fish flakes were swaying left to right in unison. The pork we ordered moved like Jell-O. After being a good sport and not saying a word about the weirdness, my date happily announced that I’d “passed.” Yep. He’d secretly put me through his First Date Test, wherein he takes girls to this particular restaurant to see if they’re down with adventure and quirk. As it turned out, I was most definitely down with quirk, I just was no longer down with him. 

The Phantom Menace

We met online. Our first date went surprisingly well. All fluttery kinds of well. He was sweet, though somewhat of a lost soul, and a gentleman who didn’t even kiss me until the third date, declaring afterward that the evening had been a “whole lot of good goodness.” Wow, I thought, this is a real, live good guy. Unfortunately, after a few months of spending almost every weekend together, it became clear that he was also A) legitimately depressed, and B) really, truly afraid of ghosts. But, given all that “good goodness” between us, I decided I was going to make this work. Then, one night over beers, he announced he wasn’t ready for anything serious. Huh? I thought we already were! I cried, he swore it would kill him if I disappeared from his life. Then he vanished. He finally resurfaced a week later, via email, when he sent … a forward. The original email was from his mom, asking me to join some pyramid scheme she described as “an awesome opportunity.” He hadn’t added his own note.