Dates From Hell (Cappuccino Edition #1)

After reading this, you'll never want to go on another date. Ever.

How it’s supposed to go. Photo by the Paris Photographer.

Some people collect stamps; I collect dating stories. I do it with the same grim fascination one sees on the faces of those beholding a car accident, say, or a ritual slaughter.

Elaborate courtship rituals have changed over time and vary according to species (the red velvet spider mite, for instance, builds a “love nest” out of sticks, leaves, and his own sperm in order to lure prospective females), but for humans, the odds for success are especially daunting. Most men are in it for the power and ego. Most women are in it for power and vanity. Both are presenting a face that is not their own, all in hopes of beguiling an emotional and/or sexual response from the other in order to get what they want. A cynical assessment, I know, but more often than not, an accurate one.

Sex may be the ostensible goal, but it’s not the only goal. If it were, prostitutes would be making a lot more money. No, it’s actually conquest. And conquest is all wrapped up in ego, vanity, power, and the desire for twenty seconds of neurochemical transcendence.

With those dynamics at play, is it any wonder that I find the horrors of dating so irresistible?

Here then is a starter pack of three hopelessly heteronormative dating stories to get you feeling better about yourself and your status, whether single or coupled. Are they cautionary tales? A damning indictment of the Way of Things Today? The end of chivalry? You decide.

Jason, 32, New York, New York.

Dating in Manhattan is hard. Everybody’s got an agenda, and there’s a whole lot of people looking for the BBD (Bigger Better Deal). My aunt suggested I try one of the online dating sites, and since I was feeling adventurous at the time, I dove in.

My first date was with a woman named Doreen from Long Island. No one looks like their profile pictures, but damn. We agreed to meet at the Grand Central Terminal on 42nd Street, and I was … is surprised the right word? She had lots of wavy brown hair, a ton of makeup, and was pretty in that hard-ish Long Island way. But I probably wouldn’t have worn the crop top. I’m not into rail thin women, but a flabby midsection isn’t the first thing you want to show on a date, right?

I thought, okay, maybe she’s got a great personality or a wonderful soul. This restaurant called Pershing Square was right across the street, so I suggested we grab a bite. Doreen gave me the side eye and shrugged. She was sipping on a Big Gulp and decided to offer me some.

“What is it?” I asked.

“Beer.”

I’m thinking, beer? In a Big Gulp? I said no.

After taking one last draw, she mumbled, “Let me get rid of this,” and literally threw the Big Gulp like a football in the middle of 42nd Street. What a classless, awful thing to do. But I’d already invited her to eat with me. I was stuck.

She ordered the most expensive thing on the menu: a dozen oysters and two glasses of white wine. After her second glass, to say nothing of all the beer she drank previously, she slitted her eyes at me and said, “You think you know me, don’t you?”

“What?” I replied.

“You don’t know me. You think you do, but you don’t. And you’re not my type anyway.”

“Uh, okay.” What are you supposed to say to that? I kept eating and looking out the window. This date couldn’t be over fast enough.

Ten minutes—or was it ten hours?—later, Doreen stood up. “I gotta pee.” She traipsed off to the bathroom, and I felt my shoulders deflate. Across the table from me was her crumpled napkin, drained glass, and empty oyster shells, a metaphor for my state of mind.

The waiter stopped by to bus our dishes. “Date from hell?” he muttered.

Nothing could have broken the tension better than that one sly comment. We both laughed. I kept laughing even when it became obvious that Doreen had climbed through the bathroom window and wasn’t going to return. I paid the bill and went outside, glad I’d brought an umbrella. Rain came down in torrents. Then I decided the only thing that might cheer me up was a Ben & Jerry’s ice cream, so I got two scoops with sprinkles, took one bite, and half the ice cream plopped on the floor.

Some days, you should never get out of bed, let alone go on a date.

Your date. Photo by Alessio Zaccaria

Shannon, 23, College Park, Maryland.

I was walking with a friend across this store/restaurant/pedestrian complex in Baltimore called the Inner Harbor, and this gorgeous man came toward me. After we passed each other, we both turned around and stared.

His name was Mike. He asked me for my name and phone number, and of course I gave them. We talked on the phone. He told me he was a competitive bodybuilder and had won the title “Mr. Maryland.” Sure enough, I saw his photos online, and could actually feel the heat in my face. Mike didn’t seem like a brain trust, but when a guy is that good looking, who cares? He also worked as a male dancer at a ladies’ club, which made perfect sense.

We got together a few times. I won’t lie. It was sexy. Then he called me really late one night and said, “I need a place to crash for a few days.”

Barely awake, I said, “Are you in trouble?”

“I’ll explain when I get there,” he replied. “But I can’t f*** you because there’s something wrong with my d***.”

Now I was really alarmed. Something wrong as in something contagious? Was there a medical problem here I needed to know about? Mike showed up looking pretty sweaty and disheveled, which made me think he had more to worry about than his sexual apparatus. He was carrying a black satchel, almost like a large medical bag, that didn’t really “go” with him. Mike was more of a backpack kind of guy.

“I broke my d***,” he told me. “I was working at the club last night. You know how we tie off before we go on stage, right? I forgot it was on. After the show, we all went out and got hammered. The next morning, my d*** looked like a purple Tootsie Roll. I had to go to the ER to get the rubber band cut off.”

Previously, Mike had explained to me that male dancers often aroused themselves before going on stage and then wrapped a rubber band around their respective members to keep them engorged. I’d just accepted this information as part of the preening peacock that was Mike. Clearly, I wasn’t thinking properly. Or at all.

“Oh,” I said, not sure whether it was okay to ask if the damage was permanent. “But why do you need a place to stay?”

Mike fidgeted, but didn’t answer. Glancing at the bathroom, he said, “Mind if I take a shower?”

I sat on the couch and listened to the water run. The black satchel sat to my left. For some reason, I couldn’t take my eyes off it. Whatever Mike was running from, the answer was in that bag. I knew it. And I knew it was probably going to be bad. Heart pounding, I lifted the bag onto the couch and undid the latch. The entire satchel was full of money. Banded money, like you see in bank robbery shows. Most likely drug money.

I took Mike’s clothes, shoes, phone, and satchel and placed them out on my outside doormat. I marched into the bathroom and cranked off the water. “Get out,” I said, handing him a towel. “Don’t come around here anymore.”

He didn’t argue, which was kind of amazing when I look back. Fortunately, I never saw him again. Moral of the story? The handsomer the guy, the more likely he’s up to something. Don’t be a fool.

Margaret, 53, Phoenix, Arizona.

On his dating profile, he said he was a widower. I was very new to the dating scene, having been married for twenty-three years and divorced for six months, so like an idiot, I believed him. We got together for dinner and drinks at a nice restaurant, which he paid for. I appreciated the gesture. Afterward, he said, “There’s this nice little tavern nearby where everybody knows me. Let’s stop off for a nightcap.”

I don’t usually do that much drinking, but I knew how to use Uber, and said okay. We went inside, and sure enough, all eyes were on us. Not in a cheerful way. More like shock. That should have been my cue to go home, but Ted seemed so legit, at least to this dating newbie. We sat down and ordered Bailey’s.

I stopped with one, but Ted didn’t. He had four or five. I grew increasingly alarmed. Sure, he was heartbroken about his dead wife, but I wasn’t going to get involved with an alcoholic. That was why I divorced my last husband.

Hours went by. We had a sizable bar tab by this point, but I was perfectly sober because Ted did all the drinking. He tried to pay, but his card was declined. While he was arguing with the bartender, a woman came storming into the bar. She was a beautiful woman about twenty years younger than me. My first thought was she must have been his daughter, but then she started yelling at him, calling him a “cheating a***hole,” and threatening to divorce him. Someone from the bar had obviously tipped her off. Looking at her, all I kept thinking was, why on earth was he trying to cheat on her with me?

He was so cowed and contrite and pathetic, I ended up feeling sorry for him. I paid the bar tab, even though I didn’t want to. Then I put him in the passenger seat of his own car and drove him to a motel where I planned on Ubering home. Halfway there, he vomited all over the front seat. There was barf on my handbag and my sweater. I had to throw both of them away.

I never did figure out why he was dating or why he was dating me. But that was enough to put a damper on my dating ambitions for quite a few months. Dating is like going to an animal shelter to find a pet. Sure, there are some great dogs and cats in there, but you’re going to come across the biters and pee-ers, too.

At this point, if it happens for me, it happens. If it doesn’t, it doesn’t. Either way, I’m pretty Zen about it.

And there you have it. Cappuccino’s first of what will hopefully be many war stories from those who have the courage to go looking for love. Do you have any “date from hell” stories? If so, your story could be featured (anonymously, if you wish) in Cappuccino’s future edition. Feel free to comment below or drop me a line here.

Amor vincit omnia!