The Best Worst Dates

This is for all of you who’ve just come home from a terrible date. Because…so what? Stop moping. Call up your friends, get a drink, share the story and laugh your ass off.

To help you with that, here’s a small compilation of hilarious, terrible dates from friends, family, and me. I promised everyone I’d keep this anonymous, so I’ll only disclose which disaster was mine…maybe. Lol

Tour-de-France

(man on date with woman)

I met this woman online. I know that for first dates women feel more comfortable in public places and during the day, so I suggested that for our first date we meet at the park. I said that we could go for a relaxing bike ride, get some ice cream, chat somewhere etc.…I wore some slacks and a casual shirt.

This woman shows up at the park in mad-tour-de-France biker gear. We start biking and she just shoots off at full, racing speed! I’m an active guy but I could barely keep up. Plus, you could see from my clothes I wasn’t there for a f%$@ing Olympic race.

I was sweating my ass off, not knowing what the hell was going on here. Not a single word of conversation. Just mad-woman tour-de-France insanity through the entire city for THREE HOURS! No exaggeration. Three hours. I kept checking my watch. At one point I yelled out that we should stop for a snack and actually chat and get to know each other, and she called me wimp. I’ll admit that my man-pride was the only reason I finished that date instead of biking off in a different direction when she wasn’t looking.

Ferrari Bathroom Escape

(woman on date with man)

I was meeting this guy at noon, for lunch. I parked the car and was walking over to the restaurant when he started texting “did you stand me up? I’ve been waiting.” I looked at my phone and it was…12:01.

So, 12:02 I arrived at the patio where he was sitting and he was quite hot to be honest. But, it was that kind of creepy, serial-killer-CEO type of hot — the perfect hair parted in a precise spot, the spotlessly clean Ferrari parked across the street — and he had the personality to match. After requesting the details of my ‘lateness’ for the first ten minutes of the date he then sat silently and stared at me.

We had already ordered food so there was no escape. Not having a clue what to talk to him about I lightly said that I’m new to the online thing but I’ve heard some hilarious stories from my friends and asked him if he had any good tales. He responded in his serial-killer monotone “I once met a woman at a restaurant. She excused herself to go to the bathroom and when I looked outside I saw her climbing out the bathroom window and running away”.

At that point, I was sitting there…holding in my pee… and wondering if I could pull off the same trick.

Lunch mercifully ended, I shook hands with him, turned, and walked away in the opposite direction towards my car. I hadn’t even reached my car (as you remember, it was parked precisely two minutes away), when I received a text from him “So, when are we having sexual intercourse?”

I managed to get to my car in 30 seconds.

‘Whip’ it Gal

(man on date with woman)

I went on a dinner date with a woman. It was our second date and we were hitting it off really well and at the end of the evening she invited me over to her place.

We get to her place and start making out when she stops me and says “hit me”. I was like “huh?”

She says again, “I want you to hit me. I’m really into BDSM. Beat me up.”

So, I say, “Ok. Well, I can be into BDSM too but you know, it’s our first time. We should get to know each other a bit sexually. Like, I’m not sure I’m comfortable with being rough the very first time I’m with you — I don’t know you. I don’t know what’s too much and I don’t want to hurt you.”

And then she tells me that if I’m not at least going to whip her then she doesn’t want to have sex. She won’t have sex unless she gets beat up. Ever.

That was one of the few times I chose to run for my life instead of having sex.

A Pitcher and a Little Lip

(woman on date with man)

A younger guy picked me up online. I generally don’t like younger guys and turned him down but he kept persisting, saying that he felt like we really connected and he was mature beyond his physical years. So, finally I decided that maybe I was being too judgmental and I agreed to meet him for dinner.

First off, he arrived significantly late, at which point he ordered a pitcher of beer and drank the entire thing by himself. After chugging the pitcher and wolfing down his meal he asked me to front the bill. I didn’t really know how to respond and in shock I paid for him and started to say bye.

He then began to whine about how his place was soooo far and asking if I can drop him off. His place was, in fact, on the way to mine and I stupidly said ‘fine’ and agreed to drop him off, just to finish the date. When we got to his place I pulled over and said that it was nice to meet him but I did not feel that we were a good match. He started pouting and whining, and then suddenly he put his arm around my shoulders, brought his face really close to mine and said in a kiddy voice “how about some lippy-lippy?”

I just stared at him, my brain thinking “lippy-lippy?????!!!??? Did he just whisper lippy-lippy in a 2-year-old-wants-to-be-sexy voice???”

Finally, realizing that he had in fact just said ‘lippy-lippy’ in the voice of a toddler, I replied “No. No lippy-lippy.”

After toddler-begging a couple more times for a “little lippy-lippy”, he stormed out of the car, slamming the door behind himself.

***

So, did that cheer you up?

If you have a story that beats the above please share in the comments! I'd love to hear it!

Original published on Medium