Who doesn’t love a good awkward situation…I mean, as long as it happens to other people, of course! So sit back, read up, and enjoy living vicariously through these intensely awkward moments.
#15. I’ll never get that image out of my head.
“In college I lived really close to my grandparent’s house so they gave me a key and told me to “Stop on by anytime, don’t worry about calling.” So I did. My grandma was giving my grandpa a bj in the living room. I ALWAYS call now. It’s been 10 years. My grandma’s favorite marriage advice is to “keep it spicy”. More power to them I guess but I’ll never get that image out of my head.”
#14. She cut the cake right there.
“Oh boy, oh boy do I have a story. My cousin was turning 30, so we were all(uncles, cousins etc, about 30 people) meeting at my grand parents house to celebrate and cut cake. An hour or two before we all made our way there, some of us coming from that far away, my grandfather had a heart attack. Before I got there, EMTS had come and gone and grandpa was pronounced dead. While waiting for the funeral home to come and collect the body, we all crowded around and left offerings/said prayers (traditional in my culture) and it was all very sombre. My 30 year old cousins mum(eldest daughter of the deceased), however, has some problems with narcissism, so while we’re all praying she insists that we must still cut her daughters cake and sing happy birthday. She set up a stool to hold the cake OVER MY GRANDFATHER’S CORPSE and made her protesting daughter cut the cake right there while we all sit around the body and cake singing happy birthday through barely contained tears. They used this big-ass butcher knife too and the whole time all I could imagine was somebody slipping and impaling grandpa. Honestly the absurdity of it all kind of distracted from the sting of grieving, so all in all it kind of worked out alright.”
#13. While working on math homework.
“my junior year of high school i was at my tutor’s house. in the middle of the session her husband called her to tell her their dog had died while he and his friends were camping. she started profusely crying on the phone and, once she hung up, instead of asking me to leave said that she was glad i was there to take her mind off of it. i guess i’m glad i could help, but god i’ve never been so uncomfortable while working on math homework.”
#12. The last time I went there.
“I would go to a 2nd language tutor once a week & she was married to a cop. One day I arrived for my session & it was very clear that they were in the middle of an argument & she had been crying but urged me inside anyways & started going over the lesson. He then walked into the room, stood over me & told me to leave whilst she told me to stay. They then started arguing over me. It was very, very uncomfortable.
I left & that was the last time I went there. To be completely honest I have often thought back & wondered if I should have said something to someone… but to who? And what..? That something ‘felt’ off? I’ve been curious if they stayed together or if they broke up.”
#11. Alarmed and horrified.
“A group of three ladies that I recognized as regular customers were shopping. Three of the ladies are sisters but there is a significant age gap between oldest and youngest, maybe 10-15 years. The youngest sister was carrying her newborn who was a bit fussy, and at various points, she would hand the baby off to the oldest sister.
My newish coworker came up to chat with/help them and to fuss over the baby. Not knowing these women, she assumed that the oldest sister who was helping with the baby was actually the baby’s grandmother (rather than aunt) and commented good-naturedly on how sometimes babies just want their grandmas and grandmas know best sometimes.
This was, of course, the exact wrong thing to say because:
Oldest sister was of course dismayed at being an aunt being mistaken for a grandma
All three sisters were shopping for something for the youngest sister (who was still adjusting to her post-pregnancy body) to wear to their mother’s funeral. The baby would never see their grandma and here’s this saleslady waxing on about how important grandmas are.
The three sisters burst into tears which of course set the baby off as well, which caused everyone around to stare. They were still staring when the middle sister (not being flooded with post partum hormones or the adrenaline that comes from being mistaken for your sister’s mom) eventually was able to explain the situation to my very alarmed and horrified coworker.”
#10. They just looked shocked.
“Not my story but a family friend.
He’s a school principle, and he goes to a wine festival and on his way home (slightly drunk) on the train he runs into the parents of a boy he used to teach. They get to talking this and that when my family friends asks how the boy is…
The parents just look shocked and say “he passed away last year… you were at the funeral… you spoke” .
He apologised profusely, but I think that’s the most awkward story I’ve ever heard.”
#9. We slowly and quietly left.
“Went into my girlfriend’s dorm to chill. We saw that her roommate was fully under her covers probably watching some TV show, so we said “hi” and laid down and chat for a bit.
She probably had her headphones on really loud or something because then we hear a vibrating sound while we were talking.
Neither of us address it and just go “ah ha ha, what’s that sound?” After 10 minutes or so it gets heavier and it looks like she’s moving under the covers. Then we addressed it to each other and decided rather than letting her know loud and clear that we’re in the room, we just slowly and quietly left.”
#8. Teenage me.
“Teenage me didn’t have a car yet. I went to go ask my mom if I could take it to go get ice cream with my sister. Got to my mom’s room and she was crying really hard. Her best friend’s son who was my age and I had been familiar with growing up had just committed suicide by stepping in front of a train. I don’t know how I could’ve been that heartless, but I still asked to go get ice cream.
Edit: spelling”
#7. The stink eye.
“Attended a memorial/funeral in Japan for an American sailor. His wife was there, and his ex-wife was there also, and his Japanese “wife” was there as well. It was rumored that there was also another girlfriend but if there was, she didn’t show. The best part was the poor dude giving the eulogy talking about what a great person this guy was while these three women are giving each other the stink eye.”
#6. I pretended I was asleep.
“When I was 11, my family had a BBQ & they invited some friends who had kids that imo were “super cute”. I was a hot mess of a tomboy so I high tailed into the shower thinking I had time before they arrived….boy, was I wrong.
I got out of the shower in my towel to hear the boys already serving their plates. I quickly go into my room. Now this room didn’t have a lock & my room was the unspoken-designated kids room to eat in & play, I hear their footsteps coming closer & I duck into closet. I’m in a towel, hair frizzy, water dripping on to closet floor…I hear the boys sit on the bed, turn on tv & eat delicious BBQ.
Then, I guess, my mom & aunt notice I’m not there & that’s not possible since I love food I shoulda been first with my greedy ass. Search begins…The boys don’t even bother to leave when their mom came in to tell them to help find me…instead they open closet door to find me. (Now I assume it was a sarcastic attempt in searching lol) I panicked when they reached the closet and pretended I was asleep…they shook me to ‘wake’ me up and told everyone I was asleep in a towel in the closet. Commence house wide laughter, even the boys were laughing!! I still feel the awkwardness and that was like 30 years ago haha.”
#5. They weren’t taking chances.
“I was visiting my girlfriend (now wife) in college one weekend. We went to a party and I ended up having WAY too much to drink and blacked out. We get back to her dorm room and both fall asleep (I’m definitely in her room next to her at this point).
I wake up on the floor with a bunch of blankets on me and a trash can next to my head. Must have been getting sick? I stand up to crawl back in bed to my girlfriend, but there is a woman with different color hair in her bed, and the sheets are different, and the shit on the walls is different too. That’s when I panic and sprint out of the room, but I’m still super drunk and I tripped on the blankets on the floor and fall flat on my face. I walk out into the hallway with a bloody nose and I’m out of breath. Girlfriends room is right across the hall.
I walk in and she is sitting on the bed pissed. Apparently I got up to pee an hour earlier and never came back. She went looking for me and couldn’t find me. She talked to the girls across the hall the next day and apologized on my behalf. They both apparently just laughed and said it was fine.
Their account (according to my wife): I just barged in the room complaining about something when I sat on the bed and realized that person wasn’t my girlfriend. I apologized to them and said I was lost and that the best thing to do when you’re lost is to stay put. So I sat on the floor waiting for my girlfriend to come find me, fell asleep, and they put blankets on me. Didn’t get sick, but they weren’t taking chances.
Edit: definitely haven’t gotten that drunk since.”
#4. Through the drive-thru.
“I was working as a bank teller. My allergies were going nuts. In fact everyone was. We all came into work eyes red and sneezing. Apparently the pollen count was at a record breaking high. Anyways we opened up and I help the first customer of the day. It went something like this.
Me: “Hi, how are you doing today?”
Her: “ I’m actually not feeling so good”
Me: “oh, I’m sorry. Is it your allergies? I know me and my coworkers are feeling it pretty bad”
Her: “no, I had a miscarriage this morning”
Me: “……..I’m sorry”
This was all through the drive through. I feel bad, I wish I could have comforted her a little bit, but I had no idea what to say.”
#3. Completely uncontrollable.
“I was at a Starbucks on my commute, waiting for my drink and people watching. I watched a young mother and her toddler, clearly justtt started standing holding onto the back of the chair, and had this silent moment of being charmed by them. The mother took her foot off the bottom rung and stood up to get a stir stick and WHAP, the child went slamming face first into the floor.
There was a moment of silence and then SCREAMING. There was a splatter of blood, panic, the mother screaming for an ambulance.
And I.. started laughing??????????????? It was completely uncontrollable. I wasn’t finding anything funny, I was completely horrified and yet I couldn’t stop flat out guffawing. I was covering my mouth, hysterically laughing this throaty laugh nearly in this woman’s face. I couldn’t keep it down, my face was in a horrified expression but it just kept happening. The tension in that room before I left – easily the most awkward experience of my life. I have no idea what the heck happened.”
#2. They failed to mention it.
“One Halloween I was walking with a group of friends to one friend’s apartment. I don’t remember how it happened, but they got a little ahead of me. I figured it was no big deal, we were entering the apartment complex and I had been to their apartment before.
So I get to the apartment door and knock. Nobody answered, but I knew they were expecting me any second so I just opened the door and went in.
There was nobody in the living room, so I headed to the kitchen, where I scared the crap out of some guy I’d never seen before. I turned around and ran out of his apartment, apologizing all the way.
He followed me out a bit slower and asked me what had happened. I explained, and he said he didn’t know my friends, but was just moving in.
And that’s the story of how I barged into a stranger’s apartment dressed like Velma from Scooby Doo. I texted my friends and found they had moved to a larger apartment within the complex recently, and failed to mention it.”
#1. It was my mom.
“I was on a road trip (passenger) and sexting with my girlfriend. During the steamy conversation I got a text saying “Please stop somewhere and get some sleep tonight, don’t try to do the whole trip in one day”. I assumed it was another text from my girlfriend, so I replied “well judging from how horny you made me, I don’t know if I’ll be able to sleep”. It was my mom.”
