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 SecretI'm about to go for supper with my mom's new boyfriend, she's 50. I didn't know my parents were divorced. -JustDax2341
The Third-Wheel Gone WrongI 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. -The_CreamPaisano
"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. -interestingdeer
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.
So awkward...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. -Notoriousjx
The InvoiceMy 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. -pockyhockeysticks
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. -BigMilk0
The Awkward Text MessageThe 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. -VeryAngryBubbles
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.... -augustusglooponface
The Irish TwinsI 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. -UnattractiveUnicorn
The... *ahem* "Adult" English TeacherMy 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.