The Worst Date I've Ever Been On

I've been on a lot of bad dates. I've had guys ditch me mid-date because of my waist size, I had one date who erupted into a ball of rage at random, and yes, I've also had one date who thought it was appropriate to show up four hours late and drunk.

But, as bad as those dates were, nothing quite was as bad as what happened with this guy. For the purpose of this story, I'm going to call him Richard.

To fully understand what was up with this date, I have to explain what's the deal with me and Richard. Richard and I have history, and that's what makes this such a shitty date.

The Backstory Between Richard And I

Around ten years prior to this date, Richard and I used to date. Back in the day, I was the only girlfriend he ever had that he never slept with. The relationship we had was one that was deeply passionate, but completely and utterly sexless. I was his "pure girl," as he called me.

If you were to have looked at us talking, we seemed like we were just friends. Or, more realistically, it looked more like two heavy drug users talking. Part of this is because we were both deeply insecure about ourselves when we were dating.

You see, Richard was the guy who introduced me to the hard partying lifestyle I am famous for today. When I first started talking to him, no one ever invited me anywhere. So, when he invited me to his first party, I went nuts for the scene—and him.

In my eyes, he had this imposing, edgy vibe about him and I was this stupid nerd who would just tag along, do whatever he said, and just feel honored that he'd let me in his circle of hard-partying friends.

In his eyes, I was a super-hot model who could dance better than anyone else around him. Meanwhile, he was this nerd who only had female interest because he threw parties.

He ended up hiring me as a professional dancer in his clique, and after parties were done, we'd sleep in the same bed. I was fiercely loyal to him, even when everyone around us hated him.

When we broke up, it quickly turned into a cat and mouse game. He'd try to get me back, I'd be dating someone else, he'd throw a shitfit and act like a jealous toddler. When I'd be single, I'd fling myself at him and he'd reject me out of sheer anxiety and run away.

Over the years, we kissed, had oral sex, and definitely shown each other our feelings. At one point, there was even a love triangle between Richard, his best friend Lyle, and me that almost caused an entire music festival to upend itself.

And yet, we never had sex.

Part of me built up this idea that he had to be amazing in bed. To this day, I have yet to see anyone who was as good a kisser, or who could reach first base as well as he did. It just made sense that he'd probably be able to make a person's toes go numb and that he'd be a real-life Christian Grey, right?

How He Asked Me Out

Around three years ago, Richard publicly humiliated me after the worst breakup of my life. I was so embarrassed, so mortified by his behavior, I told him that he would never see me again.

I broke up all contact with him, and even threw out the costumes I'd wear to his events. Six months later, he contacted me with a very heartfelt apology and asked me out on a proper date.

I agreed because of course, I did. Richard isn't the type of guy who dates—ever—and for me, this was my chance to get closure and also fuck his brains out.

The Restaurant

The first thing that happened when I rolled up to his house was that he was stuck inside. His mother came out and said, "Oh hi! You're Richard's friend! I'll go get him, he told me all about you."

Richard came out in a shirt covered in anime girls, a baseball cap, and a pair of silky boxer shorts, with flip flops on his feet. He reeked, and I mean reeked, of sweat. Fear sweat.

Uh, okay then.

He looks at me. I was done up in full makeup, spike heels, and wore a corset. He starts stammering and sweating, then just starts mentioning, "There's a Thai restaurant here, I can show you, uh, yeah. Japanese."

I pick him up and we drive to the Asian(?) restaurant, where we were promptly seated. They brought out fried wontons, and I tried to make some conversation.

"So, did you like the latest Rick and Morty?" I asked.

"You like sushi? I think they got sushi. Look at the tea. Curry?" he asked. He wasn't making much sense. He started to talk about vikings and dragons.

"Are you okay, Richard?"

"I like bunnies," he said.

"Bro, are you nervous or something, what's going on?"

He replied with deep, forced breaths, and staring at the menu. I really thought he was going to throw up on his menu, and so did the couple next to us, who slowly scooted away.

Somehow, I managed to order while he muttered something about "vikings" followed by "cigarettes."

He got sushi, and I complimented him on his choice. His reply was to chug an entire glass of water. Okay, at least he didn't puke it.

At one point, I kinda softened up. I looked at him. This was the man who made me who I am, and he's so nervous. It was like looking back at college-version me, and I just put my hand to show him that it's okay. I liked him regardless.

He managed to start eating after that, and we headed back to his place.

The Big Event

So, we get back to his apartment, and his mom opens the door. A tiny grey French poodle slowly walks out. I pet it and ask her what the dog's name is.

"Oh, that's just Fido, that's Richard's pet. Fido keeps him company and makes him relax when he has panic attacks," she said. Richard didn't look pleased, and quickly brings me to his room.

He popped a pill when he got home, we watched some cartoons together on his couch. Slowly but surely, clothes came off. I was getting excited. I was going to fuck him all night long, and give him a night to remember.

I got on top of him, he gets it in... and then he immediately ejaculates.

"Uh, Richard did you just-?" I asked.

"Y-y-yes," he said.

Richard looked like he was about to cry. I sat there, on top of him, trying hard to maintain a totally nonchalant expression, but failing because I was clearly so disappointed.

This was what I was fantasizing about for years? This was the whole sexual tension finale? Are you fucking kidding me?!

I then burst into laughter, which was probably the worst thing I could have done to that poor man. I then crawled off of him, and tried to think of what to say.

"I'm lame," he said.

"No you're not, it happens to everyone-"

"I'm lame. I'm lame," he said. Somehow, his eyes started to look beedy, kinda like Fred Fredburger after Grim hits him in that one episode of the Grim Adventures of Billy and Mandy.

"No, like, you're alright..."

"I'm lame."

It Gets Worse

For the next 15 minutes, this naked man is doing nothing but crying and telling me that he's lame. I didn't know what to do. I managed to help him get on his boxers and get him to go up for a cigarette.

"I'm lame."

"Yeah, so, Marlboro?"

"I'm lame."

I drag him outside for a cigarette, and wouldn't you know it, Fido is at the door. He picks up the toy poodle, and hugs him.

"I'm lame," he said, hugging the poodle tightly. The poodle whimpered at me, giving me a "save me" look.

"Bro, are you seriously squeezing a poodle?" I asked. "Just mellow the fuck out, it happens to everyone. Have a cigarette."

"I'M LAME!" he shouted.

He then slowly curled up in a ball on a lawn chair and started hugging the poodle tighter. His mom then came out, looked at him, then looked at me. The poodle looked at me, silently begging me to save him from the crying, fetal-positioned man with a deathgrip on him.

"Uh...yeah," I said, gesturing to Richard with a "help me" look in my eyes. I was at a loss at what to do. The poodle looked up at his mom and whimpered.

"Oh, Richard's just getting that way, let him squeeze his poodle and he'll be fine," she said. She then went away inside, leaving me with the smoldering remains of what used to be a man's self-esteem.

"I'm uh, gonna go to a party now," I said. I didn't know what else to do.

"I'm lame," he said.

I drove away, wondering what I could do to try to make him feel better. I decided to send him pictures of bunnies, and after about six months, he started talking to me again.

We're friends now, and the sexual tension is gone, but that doesn't stop this from being the most heinously awkward date I've ever gone on in my life.