Thank God for AskReddit. AskReddit is like playing a game of Never Have I Ever, except you’ve never done any of the things people are asking, and all of your friends are psychopaths. Okay, so maybe not at all like never-have-I-ever. But we digress.
Recently, user OmarFromtheWire2 asked for people’s most awkward stories, and we compiled our favorites for your reading pleasure.
Get ready. It’s about to get embarrassing.
So curl into that awkward ball you know and love, because this first one is a real doozy.
The Parental Secret
I’m about to go for supper with my mom’s new boyfriend, she’s 50. I didn’t know my parents were divorced.
The Third-Wheel Gone Wrong
I was driving, third Wheeling with a buddy and his girlfriend and the broke up after a heavy argument during dinner, before the movie. I had to drive them to their own houses and I dropped the girl off last and got a whole ear full of what my buddy was like to her.
“Can I please delete this knowledge from my brain?”
I caught my sister cheating on her husband. I introduced them to each other, and I had worked with him for a few years. We weren’t really close at the time, but it sucked because he was a really good guy. She was having coffee with him at a cafe near my apartment. When she saw me she turned away immediately and tried to hide her face. I asked her about it later and she admitted it. I didn’t do anything, she begged me not to tell him and said they would be getting divorced soon. It took longer than I would have liked (3-4 months) for her to tell him and start the divorce proceedings.
This story literally makes me want to run away from my computer.
I matched with a girl on a dating app recently. She was gorgeous, really nice and funny all seemed well. We went on a few dates and finally, she invites me back to her apartment to spend the night. She told me her roommate would be gone for most of the night because the roommate’s fiancé was in town visiting and they were going to the city to spend time together.
We spend the night doing fun stuff and eventually go to sleep. I wake up in the middle of the night and need to use the restroom. Walking to the bathroom there is a dude on the couch playing Madden. I introduced myself and find out it’s the roommate’s fiancé. He couldn’t sleep either so he invited me for a quick game of Madden. We are playing a game and then his fiancé comes out in the living room obviously looking for him.
Okay, not too bad so far. But it gets way worse.
The awkward portion? The roommate is my ex that I dated for 4 years and I just bitch slapped her man in Madden. Super awkward to explain to my date why I wasn’t comfortable coming around anymore.
After the awkward stares and silence and mass confusion, she told her man to come back to bed and he listened. I returned to my dates room and, laid back in bed unable to sleep of the pure awkwardness of the entire situation. When the girl was awake I explained to her the situation and apparently they were not just roommates, but friends (did not know each other when we dated). So it was a betrayal to continue to see me on her part, and too awkward and semi-hilarious for me.
My mom sent me an “invoice” for raising me; called her to see what was up. Says that if I don’t pay the amount she’s gonna lose the house she’s living in. Lamented that I was an expensive child (read: health issues), and how she was owed this money. I hadn’t spoken to her in 4 years prior to that. Real tough situation.
God, I hope the poor woman in this next one was joking…
Was getting a drink at work and when I turned around my female coworker trapped me in a corner. She demanded to know why I don’t look at her like the other guys. “I know I’m older than you but am I not pretty?” Luckily another coworker saw us and I just walked away laughing like she just told a joke.
The Awkward Text Message
The time my sister and her boyfriend moved back in with our parents and one night he texted me from their bedroom that he was starting to have feelings for me. Since then, they broke up, worked out their differences and figured out what was going wrong in their relationship, got back together. They are now doing very well, they have two sons and are engaged. We never talk about that text.
How about an awkward story in front of someone’s mom!
This chick asked me to be her BF while her mom was driving me home and we were in the back seat, it was really awkward when I said no….
The Irish Twins
I went to school with a set of twin girls. The first one got pregnant super young. Then, after her baby was born, her twin got pregnant. At the baby shower for the second twin, the twins’ Mom is saying something about both of them having learned their lesson and not having any more babies for a long time. She noticed the look on the first twin’s face and started freaking out. Twin one was pregnant again. The mom was standing between the guests and the door yelling at her two teenage pregnant daughters. Super awkward.
The… *ahem* “Adult” English Teacher
My high school English teacher read us erotic poetry she wrote about her husband… who happened to be our History teacher.
No, I don’t remember any of the poetry- it was too painfully awkward to absorb. A few more interesting tidbits though:
- She was significantly older than him. When they got married he took her last name.
- He used to sweat through the armpits and bellybutton areas of his shirt every day. Like buckets of sweat.
- Much later, when I was pregnant with my son, they were sitting in the OB’s waiting room across from me at one of my monthly visit. Trying not to make eye contact was as painful as the poetry reading.
They were nice people, just very strange and possibly too progressive for our small town.
The Crude Couch Surfer
My old roommate offered a dude our couch to sleep on if he paid for the cab home. I got in the cab not knowing their little deal.
We get home, she then staggers up the stairs, completely shitfaced. I hear him pacing around downstairs and ask if she had made him a bed or like, wtf is he doing here? She tells me about their deal, and I make her give him a pillow. Whatever. He sleeps. She ends up falling asleep on the couch opposite him.
It’s the morning, and I wake up to her coming into my room to tell me he woke up and immediately whipped his dick out and started beating off. She tells him it’s fine and to “not cum on the couch”, despite it not being fine.
She’s obviously uncomfortable, hence why she came into my room to announce what had taken place downstairs. So I was assigned the job of telling the dude to gtfo of our house and that I don’t generally take kindly to randoms coming over and [masturbating] all over our living room.
The Creepy Roommate’s Date
My ex housemate dated this creep of a guy who once walked into my room in the middle of the night while I was getting ready for bed. Obviously I started yelling at him and my housemate went “he was just looking for the bathroom, calm down”.
They’d been dating for 6 months he knew very damn well where the bathroom was and it was not upstairs.
How about a Good Samaritan?
I repeatedly saw the church sexton stealing communion wine from the sacristy supply closet and sometimes drinking heavily on the job.
I didn’t want him to lose his employment, but also knew that I had a responsibility to report it to the pastor before things got worse.
Thankfully, the pastor listened to my request to deal kindly with the problem and decided to pardon the sexton – giving him the help (therapy sessions) he needed to overcome the stealing and getting intoxicated on the job.
The next page gets even more awkward.
All eyes on this next one…
During high school, a girl who was in my group for a class asked me publicly if I hated her bf at the time. The entire class heard and felt like everyone was staring at me.
This next one is rage inducing.
My dad told his then girlfriend he paid for my student loan and downpayment of my house because she kept begging him for money and he needed to make it look like he had none. He also figured it would make him look good. Gave my daughter all my money to help her kinda thing.
The way I found out he told her this was when she called me SCREAMING that I was selfish for taking all of my dad’s money. He’ll have nothing left for retirement you selfish piece of shit child! If you were my daughter I would DISOWN you. Good, bye. My dad didn’t defend me or anything. Never said a word.
What bothered me most though was the fact that my dad never, and I mean never gave me a dime for anything my entire life. He had to lie to make himself look good but never ever actually did anything to make himself good.
The Uncomfortable Job Interview
I was waiting in a school office to be interviewed for an Art teaching position in a middle school 7 years ago.
There was another art teacher who already worked at the school in the office and she was trying to be friendly and make conversation with me.
She pulls out her cellphone and asks me my name. I tell her and she immediately logs into Facebook and finds my profile (which I left open to the public at the time) and immediately starts reading my profile out loud for everyone in the office to hear.
“I’m sorry, what now?”
Sophomore year of uni, some random dude starts talking to me in the student lounge. He’s amusing enough, so we converse until I go to class.
After I left, Dude started telling everyone we were going to hang out later and he couldn’t wait to take me to bed.
One of the people he told this to was a male (toxic) friend of mine who had major hangups about my not being interested in him romantically.
I had to deal with the fallout of toxic friend’s hurt feelings, outrage, and anger because some stupid dude I never saw again decided to lie about me.
This poor girl didn’t know how to pray.
I grew up not actively doing religious stuff and I lived in the middle of an aggressively Mormon neighborhood. One day when I was in the third grade I was invited to one of my super Mormon friend’s house for dinner. I went and her mother asked me to say grace. Being a stupid 10-year-old with no idea how to say I didn’t know how, I clasped my hands together and mumbled under my breath for five minutes. *five minutes *. I probably would have gone longer if the mom didn’t stop me.
I didn’t have dinner with them again.
We ain’t done yet. Keep reading for more awkward stories!
The Scooby-Doo Sneak Out
When I was at college, I was in a group of three best friends – let’s call them Pete and Carl. We were super close, all three of us, but Pete and I lived together and Carl lived with other friends. In our first year, both Pete and Carl had serious-ish girlfriends. Seemed very happy. A couple of years later, they both break up with their respective gfs. Then, not very long later, Pete started secretly hooking up with Carl’s ex. I obviously found out as we lived together and saw her around our place, but Carl didn’t know and I had to lie and keep it from her. Super awkward and almost lost Carl because of it. Also, there was a lot of movie style sneaking around that now looking back is hilarious, but was very stressful at the time. As an example, Carl came over to hang out and I hadn’t realized Pete and the girl were in his room. So I let Carl in and then I hear them. So I offer Carl a drink, then proceed to purposely spill it on him so he goes to my room and I run and tell Pete to sneak her out while Carl is drying off.
It was a happy ending tho, mostly. When it looked like it was getting serious, I convinced Pete to tell Carl, and he did, and Carl gave them his blessing. 8 years later, and Pete and the girl got married and just had a baby. But Pete and Carl stopped being friends not long after college, and they say it’s because they moved away and drifted apart, but I know it’s because of this. I moved away from them both and it’s been nearly a decade and they’re still two of my best friends, so they could have stayed friends if they really wanted to.
Every awkward story compilation needs a good one-night stand story.
This one has a twist!
An acquaintance was crashing at my place for a night. We went out and he ends up bringing someone home. I crash. They’re enjoying each other’s company. Middle of the night I hear the front door open and close. Figure she left for home. Morning comes and acquaintance is sleeping in… noon rolls around and his door finally opens and hear him walking down the hallway toward where I am in the kitchen. I’m pouring a cup of coffee for him when a female voice says, “hello”. Turns out it was the acquaintance that left in the middle of the night, left the hung-over bar-girl in my house. She and I had an awkward conversation while she drank a coffee then left.
The Silent Commute
My coworker lived 40 minutes away from work, I live 15 mins in the other direction. My manager asked me if I could give the guy a ride home because his car wouldn’t start, in front of him, right after I said my only plans for tonight were the gym. The guy was incredibly nice and I got along with him really well. I didn’t want to make my 15 minute commute into an hour and a half commute and miss my workout. But I wasn’t going to make him call a cab.
Getting Trained to be Awkward:
[I was] being trained to do my job by the guy [I was] replacing. He had no idea. Three weeks of hanging with the guy, talking, learning that he thought he was going to be able to go on vacation after I finished training and how thankful he was for them hiring me.
The next person in the comments chimed in.
Ugh, I had this and she didn’t know I was replacing her until I turned up for my first day. Found out after she’d gone that the owner of the company had been sleeping with her for a year and had surprise fired her because she was too guilty about the cheating on his fiancé and had asked to call things off.
He was a real winner.
I was surprise fired in the same way because his friend had moved to our city and he wanted to give them my job.
NEVER WORK FOR A RICH KID’S STARTUP.
But do click next, because we saved some of the best ones for last.
The worst night out ever.
When I was in the military, I had just arrived to my first duty station. I was like an E-3 which is a pretty low rank. We were out at the club for one of the Sergeants going away party. My whole platoon was there, drinking, having a good time. I saw the Sergeant dirty dancing with some girl. It struck me as odd because I remember he was married. But okay, dancing is dancing I guess. I went downstairs to order some food. As I go down and I’m standing in line, I see ALL of the Sergeants wives come in giggling and laughing. They had let the boys stay out and have fun, well I guess they came out to party too. They recognized me from the actual going away party (the club was the afterparty I guess). They asked me where their husbands were. My brain kinda shit itself because I knew what was about to transpire. I said, “Uh…upstairs somewhere, I think”. They thanked me and went upstairs. I got my food and stepped outside for a second, making my way towards the other entrance to go up to the tables and eat.
Go to the next page to find out what happened.
The wives all showed up!
I was completely alone. As I’m approaching the doors, suddenly it swings open and the wives come rushing out. One of them was crying. Yep, you guessed it, she saw her husband dancing with that girl. She proceeded to hand me her fucking wedding band and engagement ring and told me to deliver them to him. Now, being a brand new member to the platoon and a low ranking Marine who didn’t really know anyone that well, I was like holy fuck this isn’t real. Before I said anything, the rings were in my hand and the wives were across the parking lot. That walk up the stairs was the longest walk ever. I get to the club entrance and bam, a fucking gaggle of sergeants all walked out like it was a movie scene. They all looked at me. I said “Uh…sergeant…your wife told me to give you these…?” He said “Okay, thanks”. To make matters worse when I went to hand him the rings, one of them fell to the ground resulting in an awkward “It’s now both our jobs to pick it up”. Then they all walked away.
The Not-So-Classic Divorce
My sister married my best mate from college, it kinda made sense at the time because he had always been around at our house, spending time with my family etc. There were no hard feelings from me, I thought they were kinda cute and a couple. Anyhoo they got married had a huge reception where my parent spent an absolute fortune inviting probably close to 300 people, not just friends of my sister and her hubby but friends of my parents to show off to at how perfect the happy couple were.. Fast forward a couple of years and my sister and her husband had emigrated to a different country and out of the blue she calls me and asks if I can visit. So I pack my bags and go on holiday. When I arrive my sister tells me that she is getting a divorce from my mate and that she has been in a relationship with a lady on the sly for a year. So I’ve got my sister who now wants me to stay with her and support her through the divorce process and on the other hand I now have my best mate who is absolutely crushed as a male doubting his masculinity (as you would if your wife of 10 years just upped sticks and declared herself lesbian) who wants me to live with him and play video games and smoke pot with him every night.
Caught between two strangers.
My brother was about 14 at the time and he rode his bike to a nearby gas station to buy a soda. On his way in, a homeless guy sitting on the curb asked him for some change. As my brother went to give it to him a guy parked in the parking lot rolled down his window and said “Hey kid, don’t give him your money!” Then someone else rolled their window down and yelled “Don’t listen to him! He can give him money if he wants to!” Then my brother had to awkwardly stand there with the homeless guy while being pressured from both sides by the onlookers while the homeless guy just stared at my brother waiting for him to decide what he was going to do.
We hope you thought those were as funny as we did. There’s nothing we love more than those weird moments that keep us up late 10 years down the line.