Years ago, I was in a ‘roid-rage meathead gym when a man loudly declared “I might be the skinniest guy here, but I bet I’m the biggest lawyer!!!” It was such a cringe moment (it was 1984) that I’ll never forget it. Tell me your best real-life dialog fails.
The guy in question was working out with his girlfriend, a beautiful younger woman who was obviously checking out the beefier guys. His outburst made even her cringe.
How about a self imposed one, and not just because it involves you 🙃
You were at a Elliot Bay Book Company in Seattle, and some how I landed a moment where not many people had been in line yet. I happened to have a really awesome conversation with you about Fight Club 2 and those "big reveal" page turn moments and it was such a great conversation. You asked me if I was a writer by chance based off my responses or understanding I suppose but when I'm nervous around folks I admire, I laugh uncontrollably like some mad person 😂 no matter what is being said or what we're talking about. I *knew* I was doing it too, and you signed one of my books "Thanks Joe, for laughing *AT* me" 🤡 I know you meant well, and I really do always reflect back to how awesome that conversation was to have that rare quiet moment with you compared to other signings I've been to! But man do I feel like a fucking idiot harkening back to it 😂
Around eight years ago I was at a bar with a buddy. This was a cool, young people bar on Queen St W in Toronto, hipster area and me and my friend (32-33) were almost too old to be there. Early on a couple of attractive young women approached us and started chatting us up. I was getting to know the one I was talking to and at some point she asked me to guess her age. I said I'd go one better and guess her date of birth.
Looking at her all David Blaine-y, I said, "September... 15... 1985."
She went absolutely blank, then after a long pause, she said "September 15, *1989*."
So I guessed her birthday, a 1/365 chance, but I made the classic blunder of telling a woman she looks older than she does. This is me in a nutshell.
A young guy assaulted an elderly friend of mine in a road rage incident.
My friend had only just started driving again after recovering from a quadruple bypass operation and he was left quite shaken.
So I tracked down the young driver and knocked on his front door.
When he opened, I didn't say a word, I just stepped forward and punched him in the mouth and he landed backwards flat on his ass.
With a look of disbelief he bleated "You can't hit me, I'm educated."
I have no idea what that meant, and I'm still puzzled to this day.
OH! When I worked as an I.T. advisor....After a few years all calls get extremely routine, formulaic...boring. Well this morning I was a bit tired but not super out of it. I answer the call "Hello. How are you? How can I help you today?" The customer introduces himself. He's quite nice. He explains his issue and when it's my turn to speak I say "Hello. How are you? How can I help you today?" And as the words come out of my mouth for a second time I'm so shocked but can't stop myself. The customer is beside himself. LOL " I say "OMG! I'm so sorry! I guess I need more coffee! A terrible case of auto-pilot!" Luckily we got through the call pretty well. It was a very strange experience. Fuuuuuuuck...
My freshman year of college I had an English class with the Dean of Feminist Studies or Feminist Literature or something like that. Bottom line is that she was the head person at the university when it came to the topic of feminism. She had a reputation of being nasty with almost everyone. Anyway, my first day I walk in with this shirt on that I found in the attic of my house. Very basic -- yellow with screen printed red letters: WE GOT BEAT BY GIRLS.
She sees it and stomps her way up to the lectern. For a while she starts with introducing the course and sort of huffing and puffing. Finally she stops mid sentence and berates me with, “You know that shirt is sexist right?” The class sits there a couple of seconds in silence and then I explain “Well, the girls made the shirt. So, I guess it’s sexist towards me?” She sort of gasped and then quickly moved on. I felt kinda bad about it actually.
I ended up having a lot of respect for her by the end of the course even though she was pretty damn mean to everyone. I remember she pulled me into her office one time to talk about a paper I wrote and said something to the effect of -- “Almost nobody understands the concepts I’m going after here, but you get it. But you don’t care. It’s very frustrating.” She was right that I didn’t care. I didn’t care about much except partying in college, but it was a nice compliment that stuck with me and made me realize maybe I was sharp enough to write someday when I decided to care.
So back in my internet dating days:
I met a women at the American Museum of Natural History for a date. She was Russian with an extremely thick Russian accent - think Natasha from Rocky and Bullwinkle. While getting on line she says "You are man. You can wait on line.". Now a smarter man would have exited stage left. I got on line and bought tickets.
Neither science, history nor conversation was of any interest to her but I did learn she had a Great Dane. I, having had dogs, made a comment that it must be a lot of work cleaning up after a dog that big, to which she responded:
Man is the most filthy animal.
Well, after seeing a movie about whales or stars or whale shaped constellations, which I paid for, she indicated that she wanted to leave.
To which I responded that I was going to stay and see the exhibits.
At least I got a good anecdote out of it.
My sister died of cancer at 32. Her husband’s boss had offered at the time of her death to pay for the funeral (because at 32- who can afford a funeral?)
After the funeral- the mortician told us the husband's boss had now refused to pay. So my sister’s ashes were in hock at the funeral home. The entire family chipped in to pay the debt down for three months. Then I went to get her urn off the shelve and pay off the remaining balance. When I got to the funeral home- the mortician was shocked. He escorted me to the grieving room. He returned with a file- and not my sister’s urn.
“I’m sorry. But she’s been stolen. Your brother paid off the balance, signed your name, and stole her.”
Horrified I queried where he took her.
“To the deep end, the asshole of the Bay Area. A Catholic graveyard in Livermore.”
Three years ago on a Sunday afternoon my wife and I were in Chinatown in Manhattan to visit our favorite pencil store. I went into a bodega to get matches because I couldn't find my lighter and had to smoke before shopping. At the time, I walked with a cane and being a bigger guy didn't exactly move fast and couldn't change direction quickly or easily.
After I made my purchase and was walking out the door, some guy, approximately the same age, who was clearly in a hurry tried to get by me and almost knocked me over so I responded in a typical New Yorker way with a string of expletives. I didn't think anything of the incident. My wife and I bought some pencils, got a coffee, and went home.
Three days later there was a double book release event at Mysterious Books. I had met one of the authors before but not the other guy. The other guy looked kind of familiar and said, "you look really familiar. have we met before?"
I'm sure you see where this is going. The guy I cussed out was one of the authors I was there to see. I didn't make the connection myself immediately and I don't know if he ever did. We're friendly on social media and I have taken a Lit Reactor class he taught so either he also made the connection and doesn't care or never made the connection.
Sorry that was longer than it needed to be. I'm still working on the whole minimalism writing thing.
I don't know if this applies to your prompt but it's very painful and cringe.
Many years ago, I decided to do something about my low confidence and poor people skills. So I started this 21 day audio-training bootcamp thing. Each day, you had to go up to 30 women and ask something. The first day, you were supposed to ask 30 women for the time. Easy enough, right? Baby steps. So I put a suit on and walked to Kennedy Plaza, a bus station. And I asked a bunch of women for the time and most usually gave it. And then I asked this one girl for the time as she was leaving Wal-Greens. She turned to me and said, "You've already asked me for the time."
"Oh okay," was my mumbled response.
That was the final approach of the day for me. God, I was so focused on getting through these 30 approaches, I never stopped to keep track of who I was asking!
I don't know if this is a dialogue fail, it's more like an ENTIRE fail lol
Oh, and I stopped doing the program after Day 3.
"He just wants another shoe in his pocket!" - My mother, momentarily forgetting the idiom "another feather in one's cap"
The real fun here was that I was in another room and heard my parents laughing like I'd never heard before. When I asked what was so funny, all they could do was gasp out "Shoe! Pocket!" It became one of those family sayings.
This happened in 2016. Reading one of Ann Rule's books about a woman who is murdered by her husband, I said to myself, "Why didn't that woman just do a little research before she married the jerk?" Then I tried googling my new husband and BAM. Up popped his mug shot under a title "sex offender." My husband said, "I didn't tell you about my arrest 20 years earlier because I was afraid you wouldn't marry me." Sad to say I actually gave him 18 months to work this all out. But we got divorced. At least I got a lot of great material for another book - which includes his arrest for inappropriate behavior towards his then 12 year old daughter, her running away to marry a drug dealer, the drug dealer husband over-dosing his 18 year old wife, my husband's efforts to get this son-in-law put away for drug dealing, and the upcoming release of the murderer who would have probably come pounding at my door for revenge. Sigh.
There was a guy in the early 90’s that went to the bars every night with his friends to pick up girls, let’s call him Ted, no Fred. He was not good at it at all. But one special night Mike, a married friend came out as a wingman and he was great - fun, light and personable. He started talking to these three ladies which was great since there were four of us. So the seven of us laughed and joked. I guess Fred had enough of the small talk so he wedged himself between Mike and the girls and said, “Never mind him, he’s got pussy at home.” Like a bullet hole in a pressurized cabin all the life was sucked out of the room. I think Fred blacked out because that’s the last thing he remembered.
In DC, in the National Press Building (where I worked at the time), celebrities and politicians came and went all the time. One evening, a female co-worker and I waited for the elevator, and when it opened, there was Jack LaLanne (remember him?) coming down from the Press Club on the top floor. He was very polite, although much shorter than I expected, and he was quite old. This was about 2006-8 or so. We all said hello and exchanged pleasantries. After we got out, heading across the lobby to the doors, my friend said, "I didn't know he was still alive." To which Jack, about five feet away, said, "I even still have my hearing."
OK so here's one for music lovers. I'm a violinist. Years ago in a high school orchestra rehearsal, one of my strings broke so I stopped playing to go over and grab another one from my violin case. The teacher/conductor stopped everyone and asked my what I was doing. I told him my G string broke. Everyone cracked up and I think my face turned several shades of red.
In 2011 I walked into a very hip denim store in San Francisco. All I wanted was a keychain, but instead overheard the gem "My dedication to denim knows no bounds." I wish I could drum up the words to describe the sobriety and confidence in the way he spoke. It was stunning.
My wife and I could barely hold our breath long enough to get out the door without cracking the fuck up, and we still somehow find a way to work that phrase into conversation every couple months. It's still hilarious.
This shit blows my mind. Carry on
I have a lot of brain fart real life dialog fails, which normally involve me clumsily using the wrong words. I was going to prepare and iron my stepsons school uniform for the week ahead, but instead declared to my husband that I was “off to go crease some shirts”. I’m also that person who has definitely embarrassingly replied with “thanks you too” when someone says “happy birthday”.
We’ve a friend who also mashed up a saying once of “shaking like a shitting dog” and “shaking like a leaf”. What came out was “shaking like a shitting leaf”!
My friend broke up with her boyfriend who had been a real needy pain in the ass for a long time and when she did, he came to her house and shouted through the letterbox “you can’t be serious about breaking up with me, I’m a fucking 10!!”
Once at university I was standing, waiting to cross the road to the entrance of my department as I did most days of the week every morning same time as soon as the signal sounded it was safe to do so. A girl in my class approached me and launched into a very awkward conversation about my ex and blah and did I know blah and blah and I floated somewhere, mortified, wondering what I could possibly say in response and whether it was her or me or a third party I should be expressing some kind of emotion about it and what was that expected reaction… and next thing I found myself on the other side of the road as the signal finished sounding. She never spoke to me again. Remembering this now, I’m wishing this happened to me more often.
I once stood in a line at a supermarket behind a woman explaining her highly successful new business venture to a friend.
“It’s sooo amazing!” she gushed. “We go right into law firms and teach lawyers how to stand up and move around at their desk.”
I worked as a legal assistant for a few years and the way we denoted which assistant sent out specific letters was with the lawyer’s uppercase initials followed by the assistant’s lowercase initials on the bottom of each letter. So all of the letters I would type would read “AA/th” at the bottom. Now unless someone called the office asking for me by name, calls were typically directed to me on the basis of the “th” initials being on the bottom of the letter they’re phoning about.
So I get a call from a woman who was a little hard of hearing and sounded very confused. I introduced myself and started to try and find out what I could help her with, and she yelled: “Wait, what’s your name?”
Not an uncommon response to my uncommon name. I told her again that my name is Teal.
“Can you spell that for me?” the woman asked.
I spelled my first name out for her, T-E-A-L, and she commented that it’s an unusual name - a typical call.
“My name’s Ruth, are you th?” she asked.
“Yes, I am th.” I answered as I tried to remember if I had sent anyone named Ruth any correspondence in the weeks prior.
“No... Are you tee aitch?” she asked again, stressing each syllable and sounding even more confused than before.
“Yes, Ruth. I am th, those are my initials on the letter! What can I help you with?”
A few seconds of silence after I asked that.
“What?! No, my name is RUTH... RUTH. R-U-T-H!”
This poor woman was just trying to spell her name for me - the fool on the other end of the call - and her confusion was growing with each ridiculous “answer” I was giving her.
Turns out she just phoned to make an appointment to open a file with the firm, as a prospective client. Needless to say Ruth didn’t end up showing up for her appointment.
"I'm a published author!" Im not going to give any details as to who said this, or how many times I heard it, except that I frequently replied with...
"Youre an embarassment."
They also said "I already have to grease my ego to fit it through the front door." Which was a hilarious win in my book.
When I was younger I had a job interview for a waiter position. The interviewer asked, what was my greatest accomplishment? At that time I had nothing to say, so I replied, "I haven't been to jail yet." I didn't get the job.
I overheard a lady saying “I’m taking my son to the doctor. The school doesn’t want to test my son for ADHD, they think he’s intellectually impaired. I’ll do the test myself, then.”
Shit kinda broke my heart...
I've been dying to ask you this. Where the hell are you finding these weird stock images for your Substack posts? Does this site have a database of them?
At sixteen, I go to an arena concert with my friends. The opening band was Fuel. We’re walking to our seats before the show when I spot the singer and the guitar player walking through the crowd. I yell Fuel! They walk over to us and try chatting us up. We don’t know what to say. There’s an awkward silence after a minute and I fill it by saying “Good to be Fuel?” It started as a comment but trailed off into a squeak of a question. They didn’t respond and walked off. Imagine every silence for the rest of high school filled with your friends saying Good to be Fuel.
Both my parents are pretty big MMA fans. Especially my mom. Growing up she was never a fan of blood and violence. Yet, she has really impressed me in the past with her knowledge of fighters’ names and the names of moves and techniques. Until one Pay-per-view evening, during a female straw-weight bout, she was remarking on the bulkiness of one of the woman’s groin protectors.
“What’s up with her ‘poofta’? Why’s it so big”
“ Poofta? You trying to say FUPA?
“ Yeah!...what is that anyway?”
“Fatty Upper Pubic Area”
“Oh. That’s not what I meant. What did I mean?”
“ I don’t know. You invented Poofta you tell us?”
Laughter ensued. Mom forever lost her coolness points.
On another note, I know in Fight Club it’s no shirt, no shoes, but is there a rule about Pooftas? Are they optional. Just wondering.
As you know, my brain and my mouth are rarely connected. I think one of the worst was when I was working for a very serious elderly couple on their estate in the Hudson Valley. They were traveling, and the wife had gotten out of the car with her credit cards in her lap and hadn’t realized they’d all fallen out on the street and were lost.
After a lot of reassurance that I’d handle it, I said “Ok, love you. Bye.”
I used to work at an ad agency and our Director of Sales Promotion (this was the 80s) had an incredible talent for mixing up common cliches, especially under stress. He had no idea that he did this. Once, I asked him for clarification about a particular client’s project and he shook his head and muttered, “getting more information from that guy is like pulling nails out of your teeth.” And another classic: “this promotion will draw customers like flies on a cheap suit!”
I literally see nothing wrong with meathead gyms. Way better than today's planet fitness where they don't even want you lifting free weights. And it's way more entertaining seeing the roiders with no necks!
I went out on a dinner date with a woman once (I was 22) and we both knew she was older but not sure by how much. To get it out of the way I suggested we say what we were doing when John F Kennedy was shot. She said you go first. I said I had just come in from 3rd grade recess after lunch. She turned red as a beet and said she would buy her own dinner. She was a freshman in college - 10 years older. From then on I acted like a 3rd grader. Dinner did not go well.
When I was a young boy my Mom went down to the local store to buy supplies to make me poutine. When she got there she asked them where she could find the stuff to make my son poontang.
All these cool stories and I all can think of is the time my mother called me a sonofabitch.
I have trouble recalling such things when put on the spot - but here's one.
First, there are two things you need to know. One - my brother-in-law is an engineer and had, at the time of this story, been working at some sort of rocket facility. Two - the front door to my parents' house had, at the time of this story, been tricky to latch.
So, many moons ago my sister had invited her then-boyfriend over to meet the fam. Ahead of his visit, she said to me, "Kimberly - don't embarrass me."
The time arrived, and in he walked - closing the door behind himself. Or, so he thought. The door, having not latched, began to swing back open. I called out from the other side of the house, "hey, close the door - it doesn't take a rocket scientist to figure that out." Oh, the daggers my sister stared...
I guess it wasn't too much of a fail, though. They did end up married, after all. 🤣
One that always makes me laugh was when I was at a children's beauty pageant (please don't judge, I do all sorts of odd things to people-watch) and all the dolled-up girls were saying what they'd do with a million dollars.
Everything was along the lines of "I'd give it all to cancer victims" or "I'd donate it to a charity for disabled children" and got rounds of applause. Then one girl said "If I had a million dollars I'd use it to go to the beach with my friends every single day and eat loads of ice cream because I love going to the beach and eating ice cream". The silence was deafening and the girl got kicked out at the end of that round. I loved it.
Saw someone in public repeatedly yelling, "I am an adult! I am an adult!." Seems like folks who have to announce something loudly about themselves, we come to find the opposite is true.
“My Mom won’t let me watch How To Train Your Dragon Two because Gobber’s Gay.” said my adolescent cousin.
I replied in confusion. “What do you mean gay? There’s nothing wrong with being happy. I’m gay!” He explained to my thirteen year old self what it meant.
Three years later I realised I’m bisexual. Four years after that, that same cousin came out.
At a food court, saw a 30+ year old who bragged like a 5th grader spread his arms out and in front of his friends say “I’m so fire, I’ve got main character energy.”
When I was young, my mom and brother would drive 17 hours to Florida with her new husband and his four kids. The car was jam packed with luggage, snacks, and hostility. Ross, the step-dad, love to break the tension after an argument by making jokes about things he saw while driving. For example, "look at that dog on the sidewalk there, and look at the one with four legs. Or if my mother exited the car to go into a gas station, he would shout from inside the car "are you wearing a bra?". Both of these comments pailed in comparison to his haymaker.
"OOH," he would shout, "she's fat." This never failed to get a reaction out of the inhabitants of the car, including my young self. As you can probably tell Ross, my step-dad, was a piece of shit. But he embraced it.
Anyway, after 17 hours of non-stop driving we had finally arrived at our hotel. Those moments of checking in at the front desk and walking to your room after a long drive are some of the most rewarding. You are filled with adrenaline and exhaustion.
The eight of us are waiting for the elevator in the hotel lobby, which was no shabby place. A few strangers waited for the doors to open with us. Silence as the seconds ticked away.
Finally the doors opened, revealing a single person. She was more than hefty. Not morbidly obese, but obese. Of course, all eight of us shared the same thought. Sadly only seven of us had a filter.
My little brother was around 6 at the time. He didn't know that Ross shouldn't have been saying what he was saying, he just knew everyone laughed.
"OOH, she's fat." He yelled. People gasped. The lady who had been called fat looked discouraged as she walked away. My mom, my brother and I were the only ones that got onto the elevator, as my step-family made a business decision.
I had the chance to meet a musician I’ve idolized for most of my life. I had tons of conversations in my head over the years about what I’d say to him. I knew I was going to meet him for about 30 seconds to a minute at a signing, and had weeks to prepare, or maybe over prepare. So when I get to see him, I stand there stupidly staring for maybe 20 seconds and blurt out, “You’ve had a really profound impact on my life.” He starts nodding and says, “Well…thanks for sharing that.” And that was it.
I guess it’s not that bad, but it’s the one conversation I wish I could change, way more than all the bad hitting on girls when I was young and dumb.
Don’t meet your idols applies here.
I was on the London Undergound. This is the early noughties. A C-List celebrity was stood in our carriage going so out of his way not to be recognised that he could only draw attention to himself. Hooded top. Jet black Ray Bans. Standing, despite there being plenty of empty seats available. Unfortunately nobody seemed the slightest bit interested. An elderly lady reached out, tugged on his trouser leg and said “it’s alright love, I know who you are.” What was meant as a kindness probably broke the guy’s heart. We all felt it.
Overheard in a library from a group of pre-teens... "Oh my God, no, I love body shaming. I love talking about how much people weigh." Followed by rounds of giggling. I know it made me cringe...
Years ago, a bunch of us teens, all sat in the steps of a building. Smoking Hash and drinking alcohol ( all highly illegal) one of us already passed out-- We're talking about past midnight--then all of a sudden police in front of us. One of the policemen ( in a serious tone, that's what puzzles me) said: '' Look at this guy, all passed out, I can stick my finger up his ass and he wouldn't feel a thing''. Not sure of it's cringe but, it was so funny to hear. We had to hold our laughter. Luckily we were all prepared, had everything hidden well.
Ever since I can remember I've had a habit of getting "stuck" on the second-to-last/last thought in my brain. Sometimes that very thought comes out of my mouth during casual conversation.
"What time is it?"
I got six hours and fifty minutes of sleep so I say, "Six. No--I mean, seven thirty."
When I'm standing at the counter in line at this Mexican diner that's out of business now -- this was a few years ago, in a strip mall next to the local theater -- thinking I'd like a black bean burrito with tomatoes and lettuce and cheese, what comes out is:
"Grilled cheese." My dad was pretty disappointed in me that day. It was a very quiet car ride. I'm pretty sure he has forgotten about it.
I never got a good story out of these incidents, just a lot of short-term embarrassment. Maybe if I embellish the whole "L7, motormouth" angle? I don't have the kind of patience to make it into a whole personality trait.
Mine was recent. I called my fella at work, he’s a barber—- it was rather loud and he had me on speakerphone “accidentally.” I said, “You know how Sassy was constipated this morning? Well, she pooped a dime.” Before Rob could answer back, someone in the shop said, “Well, how the hell did that get there?!” The shop erupted with laughter after another person said, “Did she keep it?” I’ll never tell. However, I am dropping off some rolled change at the bank today. 😬👛💩
Mine was certainly from my late teens. Coffee shop punk/grunge, with a Ministry tee and a flannel around my waist. I was sipping Kenya AA and playing chess when I met eyes with a girl across the room. She smiled, and I returned the smile before nervously looking away. When I looked up again, she was approaching. I froze. She pointed at my shirt and said, “I love Ministry. They’re like my favorite band.” To which I replied, “I like Ministry, too.” All slowly and carefully because I was worried I’d stumble over my words. The redundancy was palpable. I don’t know if I physically smacked my forehead or if it just felt like it. The moment was lost. She said, “Okay.” And I said, “Yup.” Then she walked away. I’m still close with several people who were there to witness, and I am mocked regularly.
It was my toddlers. Any conversation with, "The boys and girls...," they'd say "Hims and hers." Melt my dark heart, Dude! That was ~2003. Now they're grown assholes hitting me up for gas money to "come home." Yeah, I still give it to 'em. Gotta buy their love after 15.
I had a boss that would constantly misquote idioms. He would say them during large staff meetings and we would try to see who hold out the longest from laughing. My favorites were "burning the midnight candle" and "you can lead a horse to water but you can't drink to make him drink".
A chemistry teacher I was working with, whom I thought I knew quite well, was in her second trimester. A conversation between classes turned to baby names, I said, “a religious freak I know just named their child Noah, aren’t these trendy new bible names the worst?”
Months later I met her B’hai husband Joshua and new baby Noah.