Mortified People Share The Dumbest Thing They've Said On A Date.

First dates are always awkward, but they can be made much worse if you say something totally stupid...

Many thanks to all those who responded. You can check out more answers from the source at the end of this article.

1. 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"

It was very awkward.


2. Me and this girl (cousin of a friend from school) were on a date, I had just finished telling her a story about a dramatic event that happened to me when I was younger.

She said "wow, that's how serial killers are made."

A very dumb comment but I thought it opened up the door for me to say "how do you know I'm not."

Apparently it didn't come off as light hearted as I thought.

The rest of the night was just downhill and awkward. The goodbye was "see ya".

I called her 2 days later and left a message, she never called back and I just left it alone.


3. I was on a date with a lovely girl, we'd been out a few times before and really hit it off. I had a notion that this was going to be the first night we'd have sex (she asked if she could stay the night at my place since she lived across town and we were drinking) so I was more nervous than normal.

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.


4. I got this fellas, sit back. I asked a blind date if she had any cute single friends.


5. This was more just me 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."


6. I was at my ex-girlfriend's house and she broke up with me.

I pretty much begged, and while begging, used a phrase that will haunt my manhood and the manhood of every man in existence. I used a phrase that should only be used for the most manly of times.

"Put me back in the game coach!"

I've since grown bigger balls.


7. When I was 16 I was on a date and in an attempt to be funny (because you know, girls like funny guys) I racked my brain trying to come up with a funny story.

The first thing to popup in my mind was a story a friend had once told me, about a jacket he had seen one of his girl friends wearing. The brand was Identity, and the name was displayed centered on the front of the jacket, with the zip splitting the word in half. Iden | tity. Now, to a 16 year old guy's mind, that is hilarious. A girl walking around with the word "tity", basically labelling her tity's?

So I told the story and started laughing! She looks up at me with a completely numb face, and then looks down at her jacket.

This was 2 hours or so into the date. I hadn't noticed that she was wearing the exact jacket I was making fun of.



8. "So, your profile picture, was that your sister or something?"


9. This was said to me, but it fits.

Met a guy on vacation. Chatted online for a while, liked each other. Decided to have our first "real" date. While eating, guy told me a story about the time his father shoved a cat in a pillowcase and slammed it into the pavement. Told him his story was horrible and to stop talking. He apologized. Tried to make me feel better by reassuring me that afterwards, his father bashed it's head in with a shovel.


10. It wasn't a date per se, but very early on in my relationship with my ex we were on the train from CT to NY and sitting across the aisle from us was a young woman with an adorable puppy. After my ex let out an audible "aww," I somehow managed to say "I love f-----g dogs" instead of "I ... love dogs."

His response was "Do I need to hold you back?"


11. Wanting to compliment on my date's intelligence I said:

"I have met stupider girls than you, so you are really ok".


12. "Hey look you have a nervous tic.... oh, it's getting worse"


13. One time I was kind of 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" ...later I found out that she was, in fact, a virgin.


14. Visiting Manhattan, watching a Rangers game in a bar by myself. Cute girl comes up and starts chatting with me, mentions that she's Dominican. I don't remember my exact words but I somehow brought up Cholera in the first 30 seconds and that was that.


15. My date was telling me how she had mono a year or two prior, and I replied "Yeah, I thought I had mono for an entire year, turns out I was just really bored" ala Wayne's World. We are engaged now.


16. Not something I said, but was said to me.

I am taking the dude home after a somewhat awkward first date. I wasn't too into him and he was just so obviously nervous. As I am turning into the parking lot where his car is he mentions he wants to tell me something, but it too embarrassed/nervous.

"Um, I should tell you something."


"No, nevermind."

"Just tell me. I hate when people do that. Go ahead."

"Well... I just thought you should know that... I'm uncircumcised."

"Oh... ok."

In my head: WHAT THE HECK. I don't care that your uncircumcised and I'm kind of offended that you feel the need to tell me anything about your penis on our first date. I doubted very much that I would be seeing that penis anytime soon. I was so embarrassed for him!

10 months later... We live together and I see that penis far too often.


17. One time on the first date between me and this girl the topic of underwear came up. We were talking about which we liked, and which we didn't like. Stupid stuff you only talk about to make conversation. At one I responded to her "You mean the panties your mother laid out for you?"

It was a shotty reference at best, and not very funny. She had never even watched Seinfeld. The next couple minutes were a little awkward, trying to pretend I didn't just say something that stupid.


18. Technically the date had finished, and she'd invited me back to her place.

While in her room, we were slow dancing, solid, deep eye contact. I was going in for the kiss, she was deliberately teasing me by pulling away or brushing my lips with hers, had her fingers in my hair, I had my nails running down her back, the sexual tension was like electricity in the air.

She leans forward, kisses my neck and whispers in my ear "Have you ever had to work this hard before?"



19. I went a date with this guy back in college who was majoring in math. I told him that really stupid joke "Why was 6 afraid of 7? Because 7 8 9."

He didn't laugh.


20. Took a girl out to dinner, had a few drinks, go back and watch a movie at my place. Midway through the movie, boner jam's ensue. After we finish, I reached over to my nightstand for my glasses and missed, ended up hitting one of those buttons from Staples, "THAT WAS EASY!". We've been dating for 6 months now.


21. When I was 17 a girl messaged me on myspace wanting to hang out. I thought she was pretty cute so I agreed to meet her for some games at her place which her family joined in on.

She had on a shirt with really short sleeves revealing a few horizontal, parallel lines just below her shoulder. Wanting to make light conversation and being the "funny" guy that I am, I asked, "Where'd you get those cuts on your arms? Do you cut yourself?"

As soon as I finished cracking that "joke", my sheltered Utah childhood came crashing down around me as I realized that people actually did do that, and I'd just called one out right in front of her family.


22. Early on with my now ex. We're fooling around. She liked to talk dirty. She's really good at it (or maybe I'm just really easy). Anyways, each time she says something I feel the need to respond (it got her going). This has been going for awhile and honestly, I'm running out of ideas fast. Only enough blood to run 1 organ at a time ladies.

Long story short, she goes "I want you inside me." and me fumbling around trying to quickly think of something to push this perfect moment over the edge attempted to say something along the lines "I want to be inside you." (only sexier, ok not really) but instead it came out "I want your c--k.".

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 off her stares into my eyes and laughs uncontrollably for oh I'd say a good 20-30 minutes. That pretty much ended my chances for that night and many to come.


23. I went on a blind double date. My roommate and his gf set me up with one of her friends. We went to Dave & Buster's. After dinner we go to play some games. There's this one game that is a giant electric chair. You sit in it and hold on to these brass handles that vibrate intensely, giving you a very odd sensation. The point is to hold on as long as possible to achieve more tickets.

Anyway, the date was going slowly and we didn't interact much at dinner. I hop on this chair and give it a try. It feels crazy and my roommate and I are laughing our butts off. She just stands about 20 feet away acting aloof. When the chair stops I keep trying to get her to come try it. I try to get a laugh out of her by acting like I'm being shocked. She turns around and leaves. Later that night my roommate tells me that her uncle was put to death in the electric chair the previous month. We live in Texas. /facepalm


24. In college, I had just walked a girl back to her dorm after a night out. We were making out in front of said dorm, I was probably about to get laid, and I said "I had a lot of fun tonight, Heather."

Her name was not Heather. I did not get laid.


25. Senior year of high school I got setup on a date with a girl who was around my age. She was clearly into me, because she'd only really dated university guys, but she'd insisted that her friends set us up on a date. So she's flirting, and I'm flirting, and all is going according to plan. We're on our second drink (legal drinking age is 18 here) and I can see where the night is headed. So I go "so you're all single now hey?" And she smiles coyly and says "yes I am" - I swear she was just shy of doing one of those sexy winks. Then she asks me if I'm single. Well of course I'm single, otherwise I wouldn't be on a date. But in my infinite wisdom, I see that as an opening to moan and complain about my ex. Twenty minutes later the date was over and I phoned my friends to go out and drown the sorrows of my own stupidity. I learnt my lesson, though: never. talk. about. ex's.


26. This is something I said and did, but it definitely fits the theme.

So I met a girl, 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.



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