My Worst Date Ever – A Tragicomedy

A few years ago, I had a bad date. And not just any bad date; a ridiculously bad date. So, of course, I documented it. I suppose this is the lemonade I made from the giant lemon life handed me. Apologies for the dated material, but I think that while I hated it, you will enjoy my terrible, horrible, no-good, very bad date.


January 2011

I was working out at the gym, and was having trouble adjusting the settings on a machine due to my lack of strength and/or coordination. A kindly meathead noted my struggle and gave me a hand. Later, as I was leaving the gym, he followed me out. Apparently he had been calling out to me for quite some time without me realizing, since I had my headphones in with Michael Jackson “hee-heeing” at full blast. When it finally registered that I was being pursued, I reluctantly engaged in some small talk. Was I new here? He hadn’t seen me here before. Did I work out a lot? I seemed like a nice person.

This guy, let’s call him “Johnny,” was somewhat stocky and beefy, with a look in the same category as Ronnie from Jersey Shore. I think they call them “gorillas.” He didn’t look bad per se, but he wasn’t my usual type at all; I associate that kind of guy with ‘roid rage, low intelligence, and general douchebaggery. Was I stereotyping? Perhaps. But I was trying to be less judgmental. And my friends had been telling me that I needed to give chances to different types of guys without judging them from the get-go. So when this nice-enough-seeming Johnny asked me if I wanted to hang out some time, and my initial/gut instinct was a quick and decisive No, I second-guessed myself.

Fast forward to our first date. I wouldn’t let him pick me up because, thankfully, I had the foresight to not let him know where I lived. It was just going to be low key – drinks and a movie. I got to the theater first. After waiting on him for quite some time (he was running late in his effort to “freshen up”), he appeared in the dark of night bearing a single red rose, with a tiny toy bear clinging desperately to the stem. I suppose this was a sweet gesture, right? So I dismissed my “Uh…” moment and thanked him graciously before awkwardly stuffing the rose – which turned out to be fake – into my purse. It continued to hang out at a weird angle, knocking into my elbow for the rest of the night.

After embracing me in a hug and stamping a kiss on my cheek, Johnny looked at me worriedly. “Hey, so, I have to ask you something. Does my hair looks ok?  Because, you know, when you saw me at the gym it was all slicked back, but now I spiked it. I don’t know if you like it spiked. Like, what do you think? Is it ok? Or did you like it better slicked back? What do you think?”

“It’s fine,” I assured him. Oh no. This wasn’t a very good start, but I tried to be optimistic.

He made me pick out a late movie so we would have time to get to know each other at the bar/pool hall beforehand. I exacerbated the awfulness of the date by picking “The Tourist.”  But I digress. The bar was literally next door to the theater. So when we went outside to make those six steps to the bar, I was surprised and slightly uncomfortable that he grabbed my hand. It didn’t help that he had these clammy, meaty hands. I found some excuse to shift away and we went inside.

Johnny ordered us a couple of beers and then the real fun began.

“Do you mind if I ask how old you are?” I inquired. He looked twenty-eightish to thirty.

“Twenty-seven,” Johnny said. “You?”


“So…what are you?” he asked.

I assumed he meant my ethnicity since I thought it clear I was human. I explained that my parents were from Sri Lanka.

“Is that in Africa?” he asked.

I cringed slightly, but tried to give him a break. After all, Sri Lanka is not as well known as, say, India.

“No,” I replied. “Sri Lanka is an island south of India.”

“So you’re Indian?”

“No. Sri Lanka is it’s own country. It’s just near India.”

“But what country is it by?”


“No, what country?” he asked with slight exasperation. “Like, Africa?”

I blinked and patiently explained that Sri Lanka was located south of India, which was a country, and that Africa was, in fact, a continent. Then I switched gears and asked him what he did for a living.

“I’m a security guard at a blood bank.”

“Oh really? Do people try to steal blood or something?” I asked curiously.

“No. But, you know, sometimes the people who donate blood get into fights.”

This struck me as odd. “Really? Why?”

He shrugged. “Oh, you know. Sometimes they get impatient when they try to give blood and they pick fights.”

“Ah.” Of course.

“But that’s not my real job. I used to be an apartment manager, before the economy got bad. Then I lost my job.” Suddenly he fixed his eyes on me in an intense gaze. “But you know, everything happens for a reason.”

I nodded encouragingly, not wanting him to feel bad about his job situation.

“I mean, because I lost my job as an apartment manager, I got a job as a security guard. And because I got that job, I switched to a closer gym. And because I switched to a closer gym, I met you!”

Uh oh. I tried to diffuse the statement as best as I could. “Yeah, I bet you meet tons of people at the gym! The gym is a great place to make friends.”

We talked about my job for a minute and then Johnny began the Spiel, which was essentially a long, rambling speech listing all the qualities he thought made him the perfect man. “I treat a girl right. I work out every day. I like long walks on the beach. I can hold my liquor.” Etc., etc. This went on for ten or fifteen minutes, peppered with bad jokes. And every time he cracked a joke – not one of which was memorable enough for me to repeat – he forcefully smacked my leg and went, “HAH! I’m just kiddin’.” “HAH! I’m just kiddin’.” “HAH! I’m just kiddin’.” My leg was red and stinging by the end of the Spiel. The more he talked, the more I drank (well, of my single beer).  Strangely,  I experienced the opposite of the beer-goggles effect…he actually became increasingly unattractive to me. Beady eyes. Rock-hard hair. Syrupy expression. Ew.

At some point Johnny realized he should turn the topic of conversation back to me. He asked me if I lived with roommates. I lived alone, so I told him yes, I had roommates. He gave me the intersection of his residence (which was not too far from my own) and asked me where I lived. I fabricated an intersection much farther away.

The bartender threw me sympathetic – or was it pitiful? – glances throughout this trainwreck. When Johnny excused himself to use the little boy’s room, the bartender tried to make me feel better by juggling a few bottles of beer. He dropped them all, which did elicit a real laugh from me for the first time that night. When Johnny returned, it was my turn to use the restroom, and I took my sweet time.

I didn’t want to go to the movie. Just talking to Johnny had been torturous for me. But he had already bought the tickets – even though I had tried to pay for my own – and I felt bad skipping out. It was just a movie, right? There’s not a lot of interaction necessary with movies. So I thought I’d rough it. It couldn’t be that bad.

When we took our seats, I made sure my body language was crystal clear: my entire body was angled away from Johnny, legs crossed, arms crossed, hair cascading down my right side as a barrier, and armrest down. Johnny yanked up the armrest and scooched right on next to me, getting as cozy as he pleased. Did he not get it, or was it that he just didn’t care?

“So, when I meet your parents, should I wear my hair spiked or flat?” Johnny asked. “I’m guessing they’re kind of conservative, so I probably shouldn’t wear it spiked, right?”

I sneaked an incredulous glance at his face. Was he kidding? Nope. This guy was completely serious, earnest as can be. Meet my parents? What the hell? He continued in this vein, planning our future – “We should go on a cruise!” and so on and so forth. My response to each of these statements was to laugh as though he had told a funny joke and then promptly change the subject.

“Oh look, the movie’s starting!” I nearly shouted.

Johnny talked throughout the movie. And not in particularly hushed tones. And not in any way related to the movie. Mostly he broke down his workout routine and diet for me, just in case I was interested (I wasn’t).

“Do your hands get sore from typing all day?” he asked me at one point.

“Nope. Not at all,” I answered firmly, because I could sense where this was going. No matter; he grabbed my hand anyway and began massaging it with his sausage-fingers. I quickly snatched my hand away and said shortly, “I’m good, thanks.”

“Do you want to give me a massage?”

I did the laugh and subject-switch.

He brought the subject back to himself. “Yeah, I’m really sore from working out. See, feel it!” He held his arm out. I nudged it apprehensively, as though it might explode. “No, feel it!” Once again he grabbed my hand, and this time ran my hand up and down his arm. Once again I retrieved my hand. This guy was too much.

I leaned away as far as I could and focused on the movie, which wasn’t that much better. Johnny scooched in again and rested his head on my tense, angled shoulder. Awkward. When that didn’t get a response, he planted a big, wet kiss on top of my head. I was wildly uncomfortable. I felt as if I was trapped in a ridiculous, exaggerated sketch-comedy of the “Can I have your number?” variety. I couldn’t take it anymore.

For the second time that night, I camped out in the restroom. I paced in front of the mirror, seriously considering leaving. I should have, probably. Either I’m too nice or don’t have enough backbone, depending on who you ask. But I thought it rude to ditch Johnny instead of making it clear I wasn’t interested in him face-to-face. When I returned to the theater, the movie was reaching the twist-ending that I had predicted within the first fifteen minutes of the film. Johnny seemed visibly relieved that I’d come back…maybe previous dates had left him before!

As he walked me to my car, Johnny was musing what we could do on our next date. Bowling? No, we should do a trip! A snowboarding trip! When we reached my car, I was gearing up to say goodbye, but he quickly asked, “Can you give me a ride to my car?” Sigh.

I drove him back to his car with both hands on the steering wheel, body once again veering to the left. When we reached his car and said goodbye, I dodged his kiss, patted him on the back and said, “I hope we can be friends.”

“Oh….oh! Ok.” He finally got it. “Yeah, ok. You seem like you’d be a good friend.” His head hung low like a reprimanded pup.

I drove home with the windows down feeing liberated. Hee-hee!

The next day, Johnny left me a voicemail.

“Hey, it’s me…Johnny. I noticed you said that you just wanted to be friends. I just wanted to know…what did I do wrong? Was I too aggressive? I would just appreciate it if you could tell me what I did wrong so that I could improve myself and be better the next time I date.”

Dammit. He was all subdued and melancholic. I kinda wanted to help the guy. Maybe he really was just hopelessly clueless. My friends heard the voicemail and agreed that he seemed sincere, and didn’t think it would be a horrible idea to call him back.

Later, when I finally got a hold of him, Johnny sought my feedback like a rejected job candidate who had unwittingly botched an interview. I tried to be as tactful as I could. “Yeah, you were a little aggressive for my taste,” I told him. “I mean, maybe some girls are into that…I don’t know. But I just don’t think we’re compatible. You were too aggressive and I’m not comfortable being that affectionate with someone I just met. And you’re not my usual type. I knew that when I met you but I wanted to give you a chance since you seemed nice, but I’m usually more into…um…nerdy guys.” (I didn’t want to say “smarter” and hurt his feelings). “But I know there’s a girl out there who’s right for you; it just isn’t me.”

“Oh, ok. Thanks. I appreciate your honesty.” Pause. “But, you know, when I saw you at the gym…I could just imagine our lips making beautiful music together!”

I kid you not. Verbatim, ‘Our lips making beautiful music together.’

Once again, I did the old laugh-and-switch.

“Ok, well good luck out there,” I said, trying to wrap things up and say goodbye.

“Wait, you said we could be friends, right?”


“Uhh…well friends are a good thing to have,” I hedged.

“Well, you know, I’m always here if you ever want to hang out, or chill out, or make out.”

Or make out. He just slipped it right in there, that sneaky bastard.

“Um, no. No I won’t do that,” I said very deliberately, and proceeded to make it crystal clear that I was not interested in him in any capacity. I said goodbye and breathed a sigh of relief.

Five minutes later, the phone rang.

Ok, what else could he possibly have to say at this point? I was curious. I picked up the phone.

“Hey, sorry to bother you again,” Johnny said. “But I was just wondering about something. Did you believe me when I told you I was 27?”

I froze.

“Um…I don’t usually assume people are lying to me when they talk to me…are you not 27?”

“Naw, I’m a bit older. But, you know, I like to work out and keep fit, stay young.”

“How old are you, exactly?”


Silence on my end.

“But you know,” he continued, unfazed by my shocked repulsion, “I like to stay young. So you believed me, huh? That’s good!”

“You lied to me?” I finally sputtered, incredulous. “I can’t believe you lied to me by eleven years! Who does that?”

Luckily, he had a solid defense. “Well yeah. But I had to. That way I can get younger girls, like you!”

My mind was reeling and my body was cringing and still, Johnny rambled on blithely. “Yep, I like the bodies on younger girls. Like, when I saw you working out at the gym, I really liked your body. I could just put some ice cream on that thang!”

He then made a clean transition into some dirty-talk.

I hung up on him, horrified.

He’d ruined ice cream for me, at least for a while.


11 thoughts on “My Worst Date Ever – A Tragicomedy

  1. I’m sorry, Natasha, but I couldn’t help myself. I laughed my ass off. Do you mind if I reblog this on Ronin. I think some of my readers would get a kick out of this. Sorry you went through that. It was like watching a beautiful train wreck. You just can’t take your eyes off it.

      1. Well rest assured, if I were there, I would’ve thought of an evil and ingenious way to get you out of that date. Maybe I would’ve ran up to you and yelled, “Natasha, your car is on fire! In Sri Lanka, right next to Africa!”

  2. Reblogged this on Ronin Literati and commented:
    Hey everyone. Tonight I bring you the horrific tragicomedy from my good friend over at Cup of Whimsy. Here, Natasha speaks on a bad date that just seemed to get progressively worse and worse and well, worse. While it was a nightmare for her, it’s comedic gold for us. Seriously, this makes an awesome story. So without further ado, here’s My Worst Date EVER – A Tragicomedy. On a side note, Sri Lanka is next to Africa (I know it’s not, but just read the story, you’ll get what I mean).

  3. Hi…just found your blog and clicked on this story since it seemed like it had a lot of potential. It didnt disappoint! Very funny stuff. I will definitely come back and read some of your other stuff.

Penny for your thoughts? :)

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