We’ve all been there, in an awkward situation, waiting for it to pass so that we can hide our faces and move on with our lives. However, every now and then, we experience a moment that moves from ending on a sour note to a (somewhat) happy ending? The following AskReddit users share their personal “awkward to awesome” moments.
Source list available at the end.
My parents found gay porn on the computer when I was a teenager. At the time, it was mortifying. However, they made it clear that they didn’t care if I was gay. They said that they had suspected it for a long time, but that they would still love me. Awkward at the time, but great in the long run as I never had to have the coming out conversation with my parents.
I went to an NFL game and tailgated with a few of my friends. One of them brought a new girl along that he had been seeing. It was the first time that I was meeting her. I was drunk and while talking to the both of them, I asked if they were “together”. Evidently, they had not had this conversation yet, but they ended up having it on the walk into the stadium. I was invited to their wedding 3 years later.
I was hanging out at my friend’s house, and we were playing some video games. We were in front of the TV and sitting right next to each other (He was on the left, and I was on the right). His grandma came over, greeted me, and kissed him on the cheek. After a couple of hours, she decided to leave. Little did she know, we had changed seats after our split screen sides switched. She leaned over from behind 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.
I used to play co-ed soccer when I was ten. I collided with this girl and broke her arm in an accident. She had a piano duet the next week, and I felt horrible. It turns out, her partner had also broken her other arm. They ended up playing their recital together on the same bench.
I don’t know, mine isn’t exactly ‘awkward’ but it was one of those moments that meant more to two other people than me.
One night, my friends went to a pub that does karaoke every Sunday. I was drunk and butchering ‘Yellow’ by Coldplay when I saw two people slow dancing as I sang.
I was hitting notes that didn’t exist, it was bad. When it finished I wobbled down from the stage and towards my booth full of buds and booze 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.
It was really sweet, all i really remember for sure is that the girl said to me ‘what a wonderful moment, thank you.’
Everyone who was there that night still laughs about it since they know how awful my singing truly was.
I recently finished a humanities class that was basically just community service. We had monthly meetings, and last month, I was asked to be the keynote speaker at our end of the year banquet. I’m not a very confident public speaker. I tend to get the shakes, but I figured I would have no problem giving a speech to 50 or so of my peers, so I accepted the honor (Not quite realizing what I had gotten myself into).
I wrote a short speech a few weeks in advance and showed up a half-hour before the actual ceremony could begin, during socializing hour, and realized immediately that I had made an enormous mistake. The hall was packed with more than 400 students/parents/and staff, even the college president was in attendance. To make matters worse, I didn’t get the memo that it was a formal event. I was wearing jeans, slides, and this obnoxiously bright orange shirt that they had handed out to all of the seniors in the class.
I went weak-kneed as soon as I walked through the door. With 15 minutes until the start of the ceremony, I took off to the local Walmart to buy a shirt and a razor. I proceeded to shave in the Walmart restroom with the limp faucets that only dribble out a couple of tea spoons of water at a time. It took me nearly 10 minutes to eradicate my neck beard, and by the time I showed up, the ceremonies had already started. I walked on stage with a glass of water and a razor burnt face to recant my most recent dilemma as my ice breaker.
The room burst into sidesplitting laughter, and I was able to walk off the stage with my dignity mostly intact.
About 5 years ago, my very good family friend was getting married to her longtime boyfriend, and she asked me to be a bridesmaid. One day, we went bridesmaid dress shopping together and then met her boyfriend and his parents for dinner. His mom asked me what we had been up to all day and I said, “Oh, just looking at bridesmaid’s dresses!” She just gave me this blank stare like “What?” Apparently, this was the dinner where they were going to tell his parents about the engagement. We still laugh about it.
Sometime ago, I was reading about the legal age of consent. Somehow it led to me learning that it was legal in some states for first cousins to get married.
Flash forward several months, I was the only one in my genetics lab who knew this last bit of information. It was extremely awkward, and the rest of the students just stared at me, but the professor gave me candy for knowing.
I told my girlfriend that my nephew was getting a trampoline for Christmas. I spend all night building it. She blew it by mentioning it out loud later that night when one of the kids was around. Anyway, it turned out fine because I still got to jump on it.
This friend of mine was coming back from a one-year study abroad, and I was in charge of inviting people for his surprise party. I accidentally ended up adding his email on the list, so he was invited to his own surprise party. Turns out, he showed up as the pizza delivery guy, and everything went well.
I fired an employee and called the police when that same fired employee attempted to drive his vehicle into the business. I pressed charges to allow the police to arrest him. The same guy came back to the business 6 months later and thanked me for having him arrested. He told me that he needed that blunt authoritative blow to steer him straight.
I was working out of town for the summer when my sister flew in to a nearby city for her cousin-in-law’s wedding. Since the only time I had to visit with her was right after work, on the night of the event, she and I agreed to meet out in the parking lot, hang out for a little bit, and then go on our ways.
Once I arrived, she insisted I come inside and sit down at a table and get something to drink. I blanched at the idea, considering I was in my paint-and-sawdust covered stage carpentry clothes. She insisted it would be fine, and pointed out a few of the most casually attired wedding guests to put me at ease.
Not five feet into the reception hall are we when I hear this squeal of delight. “Wedding Crasher!” cheered the bridge. She bounced up to us “OMG I have a real wedding crasher!!” It was about then that I remembered the Wedding Crashers movie had been released a few short months before. Obviously she knew I was my sister’s twin, what with the resemblance and all, and she was fine with my coming in. The fact I “crashed” her wedding was just the icing on the cake.
So now there are photos in the official wedding album of me and the bride, me and the new couple, my sister and I with the bride, and so on. Every time they see us, I am joyfully greeted. It’s an honor to be their official wedding crasher, but I am still mortified that I let my sister talk me in to walking in to their wedding wearing a ratty t-shirt and cutoff jeans…
I went halfway across the world for my first job as a designer out of college. It turned out to be a very stressful, confidence-shattering experience. I reinvented myself over the year long period.
Near the end of that one-year contract, I took a month to write my resignation letter. I posted that on a forum.
A year later, someone read that and reached out to me. A few months later, he was my boss and mentor. I worked with him for the last two years, and it turned out to be one of the single best experiences of my life. I learnt so much and gained the confidence to turn my talents into a real trade.
I was working as a cashier in a local hardware store. You placed orders in the back, and they were coded with your name and would come up to the one register that we had open. Someone with a kind of generic name (John Brown?) said that they had an order from the back. I rang it up first, not thinking about it, and then the 100ish plumbing pieces that he had. I told him the total, and it was thousands more than he had expected. I told him that I pulled up his name and repeated it to him. He says, “Yes, that is me.” So, I start saying that is his order when the guy behind him interrupts and introduces himself with the same name.
While I’m ringing everything up again they start chatting. Before I know it they’ve made plans for a BBQ together, and one John Brown was going to help the other with the work at his new house. They became friends, and I had to spend another 30 minutes ringing everything up again.
One of my best guy friends and I were hanging out at a bar with our friends. We had slept together once before, but we weren’t officially dating. It was getting late, and he said that he was disappointed that he would have to leave because he had work the next morning. Mildly drunk I said, “Why don’t you tell your boss that your girlfriend got you sick or something?” -pause OOPS!- To which he replied, “My girlfriend?” He smiled, “My girlfriend?” I thought about it and smiled back. “Yeah, your girlfriend.” Then we kissed, went back to his place, and he called in “sick” the next morning. We had brunch at what is, to this day, still our favorite special brunch spot. We are engaged and cohabiting 4 beautiful years later.
Back when I had short hair, a cop pulled over my father for running a red light on our way to a UA basketball game and asked why he ran a red light. My father replied, “I didn’t see it.” The cop asks where we were headed, and my dad replied that we were going to the basketball game. I meanwhile was sitting in the backseat of the car reading my novel. The cop said exactly this, “Since your little girl is being so good and quietly reading her back there, I’ll let you go.” I told the cop, “Excuse me?! I’m a boy! Do you see any breasts on this chest, or long flowing luxurious hair on my head?!” The cop blushed the brightest red I’ve ever seen a man a blush and said, “I am so sorry.” He took out his wallet, pulled out a $50 bill, and gave it to me.
I yelled at a girl at a convenience store over something really trivial that she had nothing to do with because I had run out of cigarettes and I got angry at everything. I went back later to apologize and we ended up talking for the next few hours and became really good friends.
At our Rocky cast initiation, one of the things we did was give a male member of the cast a pregnancy test and have him take it.
Two of the cast members were dating, so we thought it would be funny to give the guy’s girlfriend the pregnancy test instead. Surprise, surprise guess what the result was?
Twenty years ago, senior year of high school, I walked to my friend’s house to ask her if I should date this girl who had been coming on to me. This friend and I had known each other since first grade. A couple of hours later, we decided to date each other instead.
We’ve been married 11 years now.
I responded to a personal ad in a newspaper. When we started trading particulars over the phone, things started to sound very familiar. I quickly realized I had already responded to another one of his ads 18 months earlier. Back then, we met once for a coffee date, after which he said he would call, but never did. I brought this to his attention, and then he remembered. AWKWARD. I was ready to hang up but then he said, “Maybe we should meet again, and give it another go.”
We’ll be celebrating our 15th wedding anniversary this year.
A couple days ago, I was sitting in my language arts class and doing an analysis of this passage. To pass the time, I texted 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 realized that I had misdialed and sent the text to my language arts teacher, who didn’t use email so she gave us all her number instead. Thankfully, she just laughed it off.
The next day, in physics, I receive a text message from her saying, “Are you bored?” Being the sassy man that I am and being 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, and the best part is that I didn’t get into any trouble for it.
My best mate invited his close childhood friend along to the beach with my girlfriend and I. 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.
I caught my mom cheating on my dad.
I knew this girl online, and it turns out my mom had met her dad online and went to go see him. Somehow, the girl put two and two together and messaged me that my mom was there. I realized my mom had been gone for days. She was not at her aunt’s funeral, but with another man. She was always a drama queen and mean-spirited. My mom then goes online (after I demand to talk to her) and tells me that my dad knows. It turns out that their marriage was failing. He wanted her to see if someone else could make her happy. So, he supported her decision to find someone new.
I go to my dad in tears and ask if they are getting a divorce. He hugs me and says they probably are. My dad is 6’5 or so and about 350lbs. 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!” 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.”
I was hanging out an awful lot with a girl I fancied. One night her sister looked at the two of us and said “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 8 years later we are happier than ever.
I was spending July 4th 2009 in a little condo in Steamboat Springs, Colo. with some good friends. Everything about the weekend was shaping up perfectly. Some other people who paid backed out so everyone got their own bed and we had more than ample amounts of alcohol and food.
The first night that we were there we started playing “Circle of Death/Kings Cup/Never Have I Ever.” We made up our own rules as we always did. One of the cards was “When was the last time…”. I so happened to draw the card and said, “When was the last time you had sex” obviously to brag about the sex I had that morning with this girl I had been seeing.
I started and the answers went clockwise. 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. Everyone finished there answers haphazardly and he stood up, walked down the hall and closed the door to the their bedroom for the weekend. She eventually followed. We proceeded to make road drinks and walk up the mountain, while the two figured it out. The rest of the weekend was sort of tough and awkward, but now 18 months later they are one of the happiest couples I know.
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 ask her, “Hey did you steal your top?”
The first words I said to my best friend.
Post are edited for clarity.