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How People Turned Awkward Moments Into Total Awesomeness


No matter how cool we are, we’ve all been awkward situations. Maybe you addressed an acquaintance by the wrong name, maybe you waved back at someone when they weren’t waving at you, maybe you decided it would be cool to blow up balloons with your nose on stage at the Grade 8 talent show and only realized halfway through that it would make you a social pariah…The point is, we’ve all gotten into situations we’d have preferred not to be in.

But sometimes, people are able to turn that embarrassment around and get something good out of it.

Here are twenty-five tales of awkward situations turned awesome.

1. Kiss Kiss Fall In Love: “My best mate invited his close childhood friend along to the beach with me and my girlfriend. They secretly had been crushing on each other for years, unbeknownst to me and each other. Long story short, I was taking pictures of them at sunset and jokingly told them to kiss. They did. That night they spilled their guts to each other and now they’ve been dating for 4 months with plans to marry. I have a beautiful shot of their first kiss on my computer.” (HumbleSuperGod )


2. Lucky Break: “I played coed soccer when I was 10. Collided with a girl and broke her arm in an accident. She had a piano duet the next week. Felt horrible. Turns out her partner also broke her other arm. They ended up playing their recital together on the same bench. (slingithajime )

3. Four’s A Crowd: “I wound up interrupting a threesome on my way home from work. They were in the car next to mine with one of their windows down, so I could hear everything that was going on. As I open my door, the girl freaks out and gets everyone to stop for a second. I get in my car, one of the guys pops out and gives me a nervous smile. I told him it’s all cool. Later that week, I was working until closing and had a party of 8 come in for a reservation. One of them recognized me as that guy who made things really awkward. They ended up buying me dessert at work, which was pretty nice of them.” (stevexr1p)

4. I Guess So?: “I was hanging out an awful lot with a girl I fancied. One night her sister looked at the two of us and asked, “Are you two dating, or what?” We both looked at each other. I said, “Would you like to be?” She said, “I guess so, you?” I said “Sure!” And, eight years later, we are happier than ever.” (Simbamatic)

5. Baby Blunder: “When I was 17, I was pregnant and planning on giving the baby up for adoption. Everyone knew this and tried to be supportive. At about 8 months, I went to a party and this guy that I didn’t know was drunk and got really excited that I was going to be a mom. He was gushing about his new baby and how amazing it is and how wonderful it was going to be for me, and how even if it seems scary it will work out and be the best thing that ever happened to me. I didn’t really say much and he was mortified the next day when a mutual friend told him that I was not planning on keeping the baby. It had literally never occurred to me that having a baby could be nice. That drunken angel was the reason I kept my daughter. She is now 14 and incredibly awesome. And we have not only made it worked, we have excelled at life and I couldn’t possibly be happier that someone’s awkward gaffe changed my entire world forever.” (MyDaddyTaughtMeWell)

6. Hey, Mr. President: “When I was about 8, my people and I went to a baseball game for the home team, and we got into that whole fancy club. My dad bends down and tells my two older brothers and me to be on our best behavior because former President Jimmy Carter was there. After we got our food and sat down, he walked over with all his bodyguards to say hello to all of us. We all politely stood up and greeted him one by one. My oldest brother walked up to him confidently, held out a hand and said “Good afternoon, Mr. President.” I walked over with my mom and said, “Hello, Mr. President,” then proceeded to hide behind my mom. My dad was grinning because of his well-behaved kids, and then my middle brother sauntered in, hand extended in the goofiest handshake he could manage, and yelled, “Hiya Jimmy!” My father’s face turned from pure joy to utter horror in a blink of an eye. Mr. Carter, along with the rest of his guards, was laughing. He simply took my bro’s hand, shook it, and walked over to my dad. He patted him on the back and said, “You did a fine job raising your family.” (jennah101)

7. Kissing Cousins: “I was the only one in my genetics lab who knew that, in some states, it’s legal for first cousins to get married. It was because of a book I’d read a few months earlier, but the rest of the students were really awkward about the fact that I know it. Still, the professor gave me candy for knowing it.” (nln4)

8. Bridal Bafflement: “When my college best friend and my cousin started dating, I joked that they’d have to make me the maid of honor if they ever got married. A few years later, they actually did get engaged and I was asked to be one of the bridesmaids. I throw her a shower, they ask me to give a speech at their wedding, etc. but here’s the thing: I don’t know whether I’m the maid of honor. And because it was based on a joke, I don’t want to ask and make it awkward. So I write two speeches, a Maid of Honor speech and a shorter, nice, bridesmaid/family member speech. The night before the wedding, my friend goes for a hair ‘trial run’ and I’m like “Hey, I’ll go with you”.  We walk in, and she introduces me as her Maid of Honour.  Glad I wrote the long speech. To this day, my friend hasn’t a clue.” (meeooww)

9. You Got Served: “When I was a young guy, I worked in this restaurant where I also was dating the banquet manager. One day I come into the office, where my girlfriend was complaining to this guy about what a turd I was being (I deserved it). His back was to me, and he was totally hitting on her, while also telling her she deserved better (she did). She went white, and he realized that something was up. He turns around, sees me, and I give him the steely look, but inside I’m cracking up at the awkwardness of the whole thing. I said something (I forget what) and turned around and left before I started laughing. She and I broke up not long after, but that guy went on to be my best friend.” (deleted)

10. Harmony: “One night, my friends went to a pub that does karaoke every Sunday. I was drunk and butchering ‘Yellow’ by Coldplay. I was hitting notes that didn’t exist, it was bad. But  I saw two people slow dancing as I sang. When it finished, I wobbled down from the stage and towards my booth when the couple raced over to me to tell me that ‘Yellow’ was their wedding song. They had been having a bad night or a fight – something like that – and heard me start to sing this and fell in love all over again.” (duhdine)

11. Ringing the Rejection Hotline: “So there was this creepy guy who was a friend of a friend of a friend, and he kept hitting me on a party. Like, he knew I had a boyfriend, but he didn’t stop.  So my love-machine scoops me up and sneakily moves my favorite ring to my left hand while our backs were turned. He proudly and quietly announces that we are engaged. Mr. Creepy skulks away, not to be seen for some time. We have been together since, and we were truly engaged five months later.” (Rooniebob)

12. Second Time’s The Charm?: “I responded to a personal ad in a newspaper. When we started trading particulars over the phone, things started to sound familiar. I realized that I had responded to another ad he’d placed 18 months earlier. Back then we had met for a coffee date, after which he said he’d call, but then never did. I brought this to his attention and then he remembered me too. AWKWARD. I was ready to hang up but he said maybe we should meet again, give it another go. We’ll be celebrating our 15th wedding anniversary this year.” (FeatofClay)

13. On The Money: “The only one I have is from when I worked at a convenience store. I sold this guy his lottery tickets but managed to screw up his numbers. We didn’t find out until he checked them the next day, and he won 300 bucks with my bad numbers.” (MrChunkz)

14. Oops: “I was spending July 4th, 2009 in a little condo in Steamboat Springs, Colo. with some good friends. The first night that we were there we started playing “Circle of Death”. We made up our own rules as we always did. As one of my questions, I asked everyone, “When was the last time you had intercourse.” The girl sitting to my right said May. Next up was her boyfriend who took a long pause, looked right at her, and said “February”. The awkwardness filled the room immediately. He stood up, walked down the hall and closed the door to their bedroom. She eventually followed. We proceeded to make road drinks and walk up the mountain, while the two figured it out. But now, 18 months later, they are one of the happiest couples I know.”

15. Don’t Play Games With My Heart: “I was hanging out with a friend of a friend when I asked if I could play her racing game with her, a game I’d never played before.She said that I absolutely could, but she’d probably “stomp me into the ground,” because she’d been playing it for the last few weeks.I was fully expecting to get destroyed by her. As we came to find out, I was better than I thought. We play about half a dozen races and I win all of them. I think I even lapped her once. She was obviously pretty peeved at the fact that, despite her weeks of playing, I had beaten her. I don’t know why I didn’t go easy on her! But a few days later, I get a message from her. We end up chatting all night, then all week, then longer. Six years later, we’re living together and living happily ever after.” (Lack_of_Wit)

16. Putting the Awww In Awkward: “My parents found gay adult videos on the computer when I was a teenager. At the time it was mortifying, but they made it clear that they didn’t care if I was gay, that they had suspected for a long time and that they still loved me. Awkward at the time, but great in the long run as I never had to have the coming out conversation with my parents.” (kank84)

17. Bait n’ Switch: “I was hanging out at my friend’s house and we were playing some video games. We were in front of the TV and right next to each other (He was sitting on the left and I was sitting on the right). His grandma came over and said hi to me and kissed him on the cheek. After a couple hours went by, she decided to leave. Little did she know, we changed seats after our split screen sides switched. She leaned over from behind me and kissed me on the cheek. I immediately blushed and turned around to see his grandmother. I felt completely awkward, but we laughed for a long time after.” (Hovik4)

18. Surprise!: “I got married just over a month ago. When we’d finally gotten through with everything and were on the elevator up to our hotel room (our family friend actually canceled our reservation and made a new one so we didn’t have to pay for it. He even ordered champagne and strawberries) we were talking about how perfectly everything went.Then we got to our room. The key wasn’t working for a minute, but we finally got the door open. WELL, we get in and there’s our champagne…uncorked. Cork is on the floor. Underwear is on the floor. Strawberries eaten. Naked people in the other room of the suite asking, “Did someone just come in?” So I walk up to the front desk and, when they ask if there’s anything they can do to help, I reply, “Yeah, our room came with naked people already in it.” But we ended up with a hilarious story, and got a voucher for a free stay and dinner for a later date.” (ColdPhone)

19. First Impressions: “I met this girl at a party and she was keeping her phone in her bra and you could see the top of it sticking out. The phone was white and to me, looked like a security tag. So after awkwardly looking in that general direction for a while, I asked her “Hey, did you steal your top?” First words I said to my best friend.” (opiary320)

20. Pass The Peas: “I used to urinate in the vegetable patch, frequently enough that it would be embarrassing if anyone knew. Six weeks later, my parents came over for dinner and complimented me on how good the vegetables tasted.” (Kingofsting11)

21. Dead Awkward: “I was canvassing for a 2008 presidential campaign right before the Iowa caucuses. My walk list said that the registered voter that I was trying to talk with here was an old (90+) lady who had voted in the Democratic caucuses several years in a row. I knock on the door and a 30-something man answered, and invited me into the kitchen. Canvassers aren’t really supposed to go in, but he was friendly, it was cold, and I could see a bunch of people just inside, so I went in. As I stepped in, I gave my introduction very brightly, “Hello, I’m canvassing for Senator Barack Obama. Is <old lady> available?” One of the women at the table looked up, and I saw that she had been crying. She said, “She died this morning.” Stunned, I started backing up to leave, apologizing as I did. I felt incredibly awkward. But as I stepped out, one of the other people said “She was going to vote for Obama, and I was going to vote for Edwards. I’ll vote for Obama for her.” (Manumitany)

22. Premature:  “I used to be a server at a fine dining restaurant.  One day, in a party of 8 or 9, one of the women had strange questions for me.I was asked if our cheese was pasteurized (all cheese that comes into the U.S. is pasteurized) and I noticed she was steering clear of some of my seafood recommendations. She was also the woman who had declined earlier. Since I was also expecting a child at a time, I asked, “I’m sorry, I don’t mean to push, but do you happen to be pregnant? My chef can prepare a nice list of things that are completely safe for you to enjoy!” She and her boyfriend look at each other awkwardly, in front of both their families and her boyfriend says, “Well, we were going to wait until after dinner to announce it but… We are having a baby…” Oops. But when I saw his father a few months later and apologized for ruining his pregnancy announcement, he told me that it was the best story he’d had with his son, and he actually thanked me!” (Philobus)

23. No Woman No Cry:  “I caught my mom cheating on my dad because of a text from a friend, and when I confronted her about it, she told me that my dad knew. Their marriage was failing (she was always a mean-spirited drama queen), and he wanted her to see if someone else could make her happy.  I went to my dad in tears and asked if they were getting a divorce, and he hugged me and said they probably were. He was in his tighty-whities at the time and suddenly breaks into a dance to the beat of “The Heat is On” by Glenn Frey singing, “The woman is gone! The woman is gone!” Sidenote: My dad is 6’5 and about 350lbs. The sight of it all was just so hilarious that I started laughing through my tears. To this day, whenever I think of my parent’s divorce, I think of this funny moment when my dad was being a big goofy man dancing around in his underwear singing his parody version of “The Heat is On.” (TheLastModerate)

24. Sounds Legit:  “I was sitting in my language arts class and doing an analysis of this passage. To pass the time, I text my friend, “I’m bored.” A few minutes later, I look up and see my teacher grinning at me. She says to me, “You do realize who you sent that text to, right?” I was so confused because I thought I had sent it to my friend, but then I realized that I had misdialed and sent the text to my language arts teacher. Thankfully, she just laughed it off. The next day, in physics, I receive a text message from her asking, “Are you bored?” Well-aware that she had a class going on, I replied, “Shouldn’t you be teaching right now?” I got a lot of high fives for that.” (MisterMH)


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