31 of the Funniest ‘Well… This Is Awkward’ Moments

‘I threw up on myself during a haircut when I was 15’
31 of the Funniest ‘Well… This Is Awkward’ Moments

We all have horrifyingly awkward moments that we will never recover from. Like the Redditor who offered his date a ride home before remembering that he hadn’t cleaned out his car. On top of the car being messy, it included an array of questionable items — namely, a chainsaw, one glove and three feet of rope. Just what every girl likes to see after meeting a guy from a dating app

To that end, Redditors have recalled the times all they could do was shake their head, laugh and say, “Well… this is awkward,” and boy, is there plenty of cringe to go around. 

 11y I was walking to class and some girl comes up behind me and smacks my ass and says 'tighter than ever'. Then she realizes i wasn't her boyfriend and sprints away. ... 3.1k
 . 11y I am a director of a child care and preschool center. I was giving a tour to a Mom and Dad that wanted to enroll their infant child. Turns out the Dad used to date the infant teacher until he had an affair and knocked up the Mom.....
sprucay . 11y My mum's friend was in line at the post office with her husband. She decided to reach behind and have a fondle of her husbands bollocks. She turned around 30 seconds later to realise it wasn't her husband. Не left quickly.
JasAkiko . 11y My doctor was doing an examination. Breathing in and out, it came time to take off my coat so he go listen to my chest. Alright, and big breasts... We both remained silent. I had the hardest time not laughing. It felt like I was in a movie. My whole life is awkward though. 2.1k
Cory_mathews.1 11y I threw up on myself during a haircut when i was 15. It was super awkward because i was halfway through my haircut so they threw away the bib, got me some water, and finished the haircut as fast as they could. ... 888
 11y At a party I told my wife's friend she looked good - for once. I have absolutely no idea why I added for once and trying to talk my way out of it just made it worse. She was cool about it, but still I felt like an ass. ... 2.5k
 11y Me: Hey, coworker! Looking snazzy today in your suit. What's the occasion? Coworker: Funeral. Me: Ooooohh.. ... 2.4k
DreadedScott. 1 11y I'm a teacher. I went to get a vasectomy and the mother of a student, with whom I had recently had a conference, was the nurse who shaved my ball-sack. ... 3.4k
poorpinto . 1 11y Was once at a restaurant with a vegetarian girlfriend. Our server asked us if we'd like to try something or other. My reply was no thanks, she's a vagina. ... 2.1k
 . 1 11y Recognized this guy i knew from middle school on campus in college. Не had grown this shitty handlebar mustache so I walk up to him and say What's up with your face?! It wasn't that guy, and i walked away backwards saying cause i dig it!! While doing pistol fingers. ... 526
Cog_Blocker . 11y I was sitting at the dinner table with my brother, mom, dad, and their friend. My dad and his friend were having a conversation and for some reason the friend said something about bukakke, but he says it wrong... My brother, being the 14 year old kid who browses 4chan, decides to correct him. This was followed by awkward silence and glares from my parents. ... 332
deilan 11y I was on my way back in to town after having been at home visiting my parents for a week and was obviously excited to see my girlfriend. After I got back in I was texting both my mom to let her know I made it in safely and my gf to let her know I was back and ready to fuck. Guess who got which text? ... 1.3k
Workat5AM . 11y Went out for drinks with some friends, and the girl I was seeing at the time. She ended up staying over. The next morning as we were leaving for brunch I went into the bathroom and it smelled awful...I immediatly turned and yelled across the house to my room mate. TURN THE FUCKING FAN ON! Later that day my room mate informed me it wasnt him. It was the girl I was seeing who neglected to own it...Needless to say I felt like a jerk ... 947
foreverwithyou . 11y Once in high school a guy passed me a note saying he couldn't stop thinking about me and at the very end it said something along the lines of look over here. Mind you, the guy was sitting next to me and there was a movie playing in class. All I see is the guy holding his erect penis and my initial reaction was to turn away immediately and watch the movie. Well that was awkward. ... 334
fairlyodd922 11y When we were in high school my friend was trying to convince this goth girl to go to summer camp with us. The camp in question was on the beach. Her: I don't think I should be in the sun that long. Him: (jokingly) What are you, a vampire? Her: No, I have skin cancer. There's no coming back from that. ... 2.1k
Dashu . 11y As a kid I was invited to a birthday party. I prepared the good old boxception packaging so of course everybody was watching with anticipation when the host was unpacking to reveal... nothing at all. I forgot to put the present into the last box. ... 520
 11y Once during a move I labeled a huge box Stacey's dildos (half of them) as a joke for my wife to see. Years later we were moving again and I had totally forgotten about it. My father in law was helping us and he came walking into the room with it, placed it down, and we made uncomfortable eye contact. Nothing was said. ... 2.9k
 . 11y I went to Sonic one afternoon for a burger. The person who brought the food to my car wasn't wearing skates like all the other employees. She seemed to be about my age (late teens) and attractive. To initiate conversation I asked why she wasn't skating to which she replied, I'm pregnant. My only response was, hmm. ... 2.5k
Dovecot 11y Haha! I can't believe this. I had the male equivalent of this. I was getting my balls checked out and she said 'Big cock please' instead of 'Big cough please'. Fucking most awkward thing ever. P.S - they make you cough whilst they cup your balls for those that don't know haha. ... 1.8k
allbrawl . 11y My most embarrassing moment was when I received a phone call from a white coworker (I'm black) screaming at me and telling me he'd cut my balls off. It turns out that his wife just gave birth to a coffee colored kid and I'm the only black guy she knows. Не blamed me for the Halfrican and hasn't talked to me since. We work in the same office, so we have about 5 well this is awkward moments a day. ... 2.1k
Jplopinyourpants . 11y My first final of my college career, I was climbing over some rows of seats to get to an empty one in a huge lecture hall. As I'm passing the last row to get to my seat in the row in front my heel comes up and kicks the desk of a female student already in the middle of her test. Not a big deal, except she had a steaming hot cup of coffee that just exploded all over her lap and her test. She looks at me in horror and pain and my response was an
A_Rusty_Lamp . 11y I was out shopping with my girlfriend at a Victoria's Secret. She had wandered away form me and I saw her looking at some thongs. I came up behind her and kissed her on the neck and whispered, You would look good in that, but a lot better out of them. It was at this time I realized that this was not my girlfriend, but a girl with similar clothing and the exact same hair color. I've never sprinted out of a mall faster in my life. ... 540
ETA_was_here 11y This happened yesterday. At a car park I spot a free spot. I usually prefer to park the car backwards, so I stop the car, put the car in reverse and want to turn backwards into the parking spot. But there is an old lady walking right pass my car, so I wait. As she walked by, she suddenly start trying to open my passenger side door. After a few attempts she finally opens the door and gets in. At the moment I am too surprised to say something. It takes a few seconds before she realizes something
mcfaddon 11y I am on my second date with a girl that I met on okcupid. We were really hitting it off. When it was time to leave I had offered to give her a ride home as she had taken the bus to get there. This was not my plan from the beginning. My car was clean but I had not made it date ready. We are walking to my car and it hits me that I had borrowed a chainsaw from my father for some yard work and it was still in the back of the car, visible
Rumassog . 11y This was back when I played high school football. I got hit really hard on a play where our team fumbled the ball. Hurt and dejected I limped off to the sidelines with my head hung low, grabbed some water from the cooler near the bench and sat down. It was only when I began to sip my water that I realized, Hey, this isn't water! This is Gatorade! But...my team's too cheap to buy Gator--uh oh... Yeah I had limped off to the wrong sideline. The entire opposing team was just watching me sit on their
beefwich 11y In high school, I made out with my ex-girlfriend on her front porch while accidentally leaning against her doorbell. And it was one of those ultra hormone-y make out sessions where we were basically trying to get all of our saliva into the other one's mouth. Apparently, with whatever model doorbell chime she had, if you held the button down, it never gave you the dong part of the ding-dong. Rather, it just continuously DIIIIIIIIIIIIIIIIIIIIINGS. Her dad was, eh, less than thrilled when he opened the door. ... 801
portugueseprawnsoup . . 11y Once I was in a working mans club when all of a sudden I needed to take a massive dump. I proceeded to empty my arse in the only cubicle in the mens toilet. As well as being a huge load of shit, it was a messy wipe so a lot of shit + a lot paper = blocked toilet. After the 3rd attempt to flush it I thought 'fuck it' and I unlocked the door to find a bloke in a wheelchair waiting to use the toilet. Не then wheeled himself in and awkwardly clambered on
thattallone . 11y Working at a village shop and being incredibly socially inept leads to some fun times. Guy comes in with his really spoilt kid. She wants a chocolate bar. The dad says 'let me just check the carbohydrates'. I start giggling because I thought the dad was being awkward and silly like my dad used to be. Не looks up and stares me right in the eyes and says through gritted teeth 'She is diabetic'. I look down at the kid. Realise at this point the child has lost her foot to diabetes. ... 787
Bigpappapunk. 1 11y Co-worker approached me after being out of the office for a few weeks, asking if I knew why she was out. I said No, vacation?. No she says, My son died in a wreck. Holy shit, I had no idea I say, to which she then proceeds to tell me that she knew I had no idea because a sorry for your loss card from the office was sent to her where everyone wrote in it and signed it, including me. The only difference was that I had written Happy Birthday with an enormous smiley face.
darkchill 1 11y Few years ago, would have morning coffee with work colleague in his office. Noticed a picture on the wall... about 15 ft away... of him and what I assumed was a rugby player standing with the Rugby World Cup. Asked him who the guy was... he replied 'That's me!' 'No,' said I. 'The guy on the other side, with you'. Не looked at me and in a very unemotional voice just said 'That's my wife.' ... 2.2k
Blu3j4y 11y When I found out that I had slept with a band member's wife. This is a little convoluted, so bear with my poor story telling skills: I met a cute girl at a bar-gig, and we were attracted to each other. We went back to my place and sexed it up. We had carnal relations a few times after that. No big ideal, just some occasional sex... Fast forward about five years - I'm in a different band, and this same woman walks in. I approach her during the break and give her a hug and make some small talk.


Scroll down for the next article
Forgot Password?