14 People Share Awkward Stories That Turned Into Hilarious Memories

Just when everything seems to be going according to plan, something completely unexpected happens — and rarely in a graceful way. These stories capture the moments when situations spiral into extreme awkwardness, leaving people with nothing to do but wish they could hit an “undo” button.

• I heard a coworker of mine was leaving, so I went up to her and was like “Omg, congratulations on your retirement!! What are you going to do?”
  Turns out she was 34 years old... © Sn***BorkGnork / Reddit

• I was at the waterpark with my new boyfriend when a man suddenly approached me and whispered, “You need help. Come with me. How could your man not warn you about this?”
  Surprised, I followed him. I knew it wasn’t my period. He took me to the bathroom and asked me to turn around. I did, confused.
  Then he pointed at the back of my swimsuit. There was a huge smear of chocolate ice cream — completely melted from the heat — right across my lower back and bottom. My boyfriend had been eating it earlier, and I must’ve leaned against him.
  I felt mortified, but the man handed me some wet wipes and said, “Happens all the time. Just didn’t want you walking around like that.”

• I once accidentally sent my grocery list to my tuition group, and later, in panic, I tapped the “Delete only for me” button instead of “Delete for everyone.” There was nothing I could do now. © Im_a_PeakyBlinder / Reddit

• Quite a few years ago, I was spending an afternoon with my best friend, who was house-sitting for a wealthy family with a pool. We were tanning topless. And I decided to send a pic to a guy I was dating at the time.
  About an hour later, a friend messaged and said he was surprised that I’d “have the courage to post something like that on my FB profile.” I wasn’t sure what he was talking about... and then it clicked. The photo I thought I had sent through text to my guy at the time... had in fact been posted to my Facebook profile, where everyone, including my grandparents, could see it.
  To make matters worse, I couldn’t for the life of me get connected to the Wi-Fi and was having a very hard time deleting said picture. Won’t likely ever live that one down. © carrmu / Reddit

• At the vet’s office, my dog decided to let out the loudest fart possible while everyone was silent. Everyone turned to look at me instead of her. © dailyfunfacts / Reddit

• As I left the beauty salon feeling fabulous and walked to my car, I noticed people staring and men checking me out. I thought, “Wow, that’s some main-character energy.” Then, at the crosswalk, a stranger casually said, “Miss, you forgot to take off your shoe covers.”

• When I was in my early 20s, I worked in a grocery store in a small town. A guy who worked there has parents who are VERY attractive. They were divorcing at the time. I made a comment one day about how hot his dad is and said, “Better watch out, I’m gonna be your mom soon.”
  He told his dad what I said, and a couple of days later, when his dad was in the store, he looked me dead in the face and said, “Sup, mama?” The dude was behind him, hyperventilating with laughter, and I wanted to absolutely die. © IngyJoToeBeans / Reddit

• I went to the Museum of Illusions in Miami while on vacation with my son. The guy who took our pictures had to text me for something after the session.
  Later, I was trying to text my son to come down from the hotel room and walk on the beach with me. I didn’t look at the recipient of my texts and accidentally sent a bunch of texts to the guy from the museum earlier that day. I realized my mistake when he texted back saying who he was.
  He didn’t seem too annoyed by it, but I felt VERY embarrassed and deleted the whole message thread from my phone, so I wouldn’t make that mistake again. © giraffemoo / Reddit

• Let me tell you something that happened once that embarrassed me. I had liked my senior for three years, and one day I finally got up the courage to smile, slip the letter into his shirt pocket, and leave in a hurry. When I came back, I realized that the letter to him was still in my pocket, and the tampon was gone! © Agreeable_Storm9400 / Reddit

• At work, I accidentally got an email clearly not meant for me. It said, “Meet me in the storage room at 3. Don’t tell anyone.” I stared at it for ten minutes, debating whether to ignore it or go check.
  At exactly 3:00, I walked toward the storage room, opened the door slowly, and the first thing I saw was someone holding confetti cannons and a birthday cake. All of them pointed at me. Someone shouted, “WRONG PERSON!” But it was too late — they all went off.

• We were in the pet food aisle of a grocery store and talking about how our dog was very old when he died and how our cat was quite old, and we weren’t sure how much longer he would have to live.
  This older woman was sharing the aisle with us, and my 4-year-old son turned to point at her and said, “So this lady...” and I had to scoop him up very quickly before he could finish his sentence. © huggle-snuggle / Reddit

• I saw my husband at the mall, ran up behind him, hugged him tight, and said, “Guess who?” He didn’t respond. Because it wasn’t him. It was a man who looked terrified.
  His wife came out of the store and said, “So this is the ‘coworker’ you keep mentioning?” At this moment, my brain decided that the best thing to do was to double down and say, “Oh great, you’re both here! Let’s all talk about this!”
  The wife blinked. The man blinked. I kept going. “I’m married, I have three kids, I don’t flirt, I barely talk to people, I don’t even go outside most days — your husband is safe, I swear! I’m leaving now because my armpits are sweating.”
  Then I attempted a dramatic exit... and tripped over a mall display of discounted socks. Still feel very uneasy when I think about it.

• I was leaving the grocery store when I heard someone yell, “STOP HIM!” Everyone turned toward me. A guy sprinted in my direction, eyes wide, pointing straight at me like I was the villain. Before I could say anything, he grabbed my cart and said, “Don’t move.”
  Then he looked inside the cart, looked at me, and whispered, “Oh no... you’re not the guy. But now we have a problem because I already yelled at everyone to stop you, and I can’t walk back empty-handed.” He grabbed a cucumber from my cart, loudly said, “This is evidence,” and walked away confidently. While everyone was staring at me.

• Kissing my boyfriend before leaving is a daily ritual. So when I fell asleep in a taxi and the driver said, “We’re here,” muscle memory kicked in — I kissed him, said, “Thank you, darling,” and walked off. The driver stayed silent. Five minutes later, the realization hit. I called to apologize and added a tip.

And here come the romantic moments that went off the rails, reminding us that love has a weird sense of humor. Ouch!