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Everyone has been on a bad date. But some of us have been much, much further down the rabbit hole. I’m not talking food in your teeth or something on your shirt. I’m talking full-stop “There’s Something About Mary” hair product horror shows. While that oh-so-memorable scene is a bit farfetched, once you read these confessions of courting gone wrong, you might find yourself thankful that the worst you ever did was get embarrassingly drunk at a sushi place.

Brumbrum21’s attempt to downplay quickly backfired on him:

After a night out with this girl I’ve been courting, we went back to my place and started fooling around. We got into my room where she knelt down and began to take my pants off. Once I was naked she said, “Wow you’re really big.” Trying to be humble, I responded, “Nah, I’ve seen bigger.”

At least Bendubendubendu had his facts straight:

[I was] hanging out with a girl I had been dating for a little while. We were talking and she brought up the fact that her biological father was a sperm donor. We had already talked about this before and I didn’t really have anything particular to keep that conversation going besides, “That really increases your chances of accidental incest, you know.”

Kiddicus made a classic Freudian slip, but still came out on top:

We finished dinner, ordered some after-dinner drinks and the check came. I prefer to pay on dates, but she didn’t like the fact that I’d paid for everything so she demanded to pick up the check. I was going to offer to pay the tip, but I was thinking about sex (per usual) so I said to her, ”At least let me pay for the sex.”

I didn’t even realize what I’d said, but her face went from a smile to a quizzical half-frown… and then she burst out laughing. She asked me if I knew what I just said and I said that I’d asked to pay for the tip. She informed me of what I’d actually said and I turned beet red, apologizing profusely.

We left the restaurant, I offered to pay her cab fare home if she was uncomfortable. She declined and whispered “The sex is free” in my ear.
We’ll celebrate our 4th anniversary on Thursday.

One can’t help but wonder how ceaRshaf managed to get through the rest of the night:

Wanting to compliment my date’s intelligence I said, “I have met stupider girls than you, so you’re really ok.”

Toastercles learned a lesson in the importance on knowing your audience:

One time I was on a “hang-out” date with a girl and we were watching a movie over at my apartment. We were holding hands and she started innocently stroking my arm. She asks, “how do you get your skin so soft?” Without missing a beat I reply with a whisper, “I bathe in virgin’s blood” I later I found out that she was, in fact, a virgin.

I’m not sure what LissieRae06’s date was thinking:

I met a guy on vacation. We chatted online for a while, liked each other. Decided to have our first “real” date. While eating, the guy told me a story about the time his father shoved a cat in a pillowcase and slammed it into the pavement, “until it went retarded”. I told him his story was horrible and to stop talking. He apologized, then tried to make me feel better by reassuring me that afterwards, his father bashed its head in with a shovel.

Highlet forgot who he was for a moment:

Early on with my now ex. We’re fooling around and she liked to talk dirty. Each time she says something I feel the need to respond. This has been going for awhile and honestly, I’m running out of ideas fast. Long story short, she goes, “I want you inside me.” I, fumbling around trying to quickly think of something to push this perfect moment over the edge, attempted to say something along the lines of, “I want to be inside you.” (Only sexier. OK, not really.) But instead it came out “I want your cock.”
Holy shit, I have never wanted to just die and fade from existence anymore in my entire life. She, on the other hand, pushes me back a bit, stares into my eyes and laughs uncontrollably for a good 20-30 minutes.

Thisiswack gives him a solid “I know that feel”:

You aren’t the only one man. Mine happened mid-coitus. She was talking dirty using the “I love your cock inside me, feels so good, yada yada yada.” I respond with a good old “I love the way your cock feels”. Now, I realize I had fucked up right around the word “cock”, so I quickly spit out a list of expletives that culminated with me just yelling, “VAAAAAAAAAAAGGGGGGGGGGGGGGINNNNNNNNNNNNNNAAAAAAAAAA” at this poor girl.

The award for best recovery goes to oskarwhale:

I went on a matchmaking date this March. The matchmaker was my gay best friend. My best friend, in all his excitedness over how cute he thinks we look together, squealed, “Let me let you in on a secret about her. Her pubic hairs are straight! Isn’t that just lovely?!”

So the guy looked at me and stammered, cup of tea trembling in his hand, “Is th–tha-thaaat tr-true?” As I was in shock over the sheer lack of discretion of my friend (and when I am shocked I always lose control of my responses) I replied, “…giggity.”

Selkies was almost undermined by his posessions:

Took a girl out to dinner, had a few drinks, go back and watch a movie at my place. Midway through the movie, boner jams ensue. After we finish, I reached over to my nightstand for my glasses and missed. I ended up hitting one of those buttons from Staples, “THAT WAS EASY!”.

We’ve been dating for 6 months now.

TheBalance thinks everything is a toy:

So I met a girl, we went on a date, everything was pretty standard. I got wayyyy too drunk, but somehow charmed this girl into bed. We were getting down to business when I felt that she had a Nuva ring, which I then proceeded to pull out of her and throw onto my erection while saying ”throw the ring, win a prize” like some sort of carnival game guy. Needless to say, she was immediately turned off. We didn’t end up completing the deed, she kicked me out, and we never spoke again.
TLDR: Don’t pretend to play carnival games with birth control devices.

The true glory comes from his addendum:

As a follow up to this, another one of the the dumbest things I’ve ever said on a date was repeating this story to my date.


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