Awkward Stories Turned Awesome

I accidentally ruined a pregnancy announcement for complete strangers. Then, months later, I was told I was responsible for their best story of their life. What are your most awkward stories turned awesome?

I played coed soccer when I was 10. I collided with a girl and broke her arm in an accident. She had a piano duet the next week. I felt horrible. Turns out, her partner also broke her other arm. They ended up playing their recital together on the same bench.

I caught my mom cheating on my dad. I knew this girl online, and turns out my mom 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—not at her aunt's funeral, but with another man. She was always a drama queen and mean-spirited, a lot. My mom comes online after I demand to talk to her and tells me that my dad knows. Turns out, their marriage was failing, and 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 350 lb. He was in his TIY what is at the time and suddenly breaks into a dance to the beat of "The Heat Is On" by Glen Frey, singing "the be is gone, the B is G1." The sight of it was so hilarious to me; I started laughing through my tears. To this day, whenever I think of my parents' divorce, I think of this somehow fun moment when my dad was being a big goofy freck, dancing around in his underwear, singing his parody of "The Heat Is On." Your dad sounds like an absolutely amazing person.

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." I said, "Sure." And eight years later, we are happier than ever. Nothing's more romantic than "I guess so, sure."

What was the tip like from that table? I wonder if he knew right away if it was a good story and tipped well, or didn't realize until he started telling people. Either way, two good stories came out of it.

A woman I work with had just had a baby and asked me to be said baby's first babysitter. We're pretty tight, which I had no problem with, considering I'm like the Pied Piper with kids—minus the leading into a cave, of course. So I am babysitting an infant and an 8-year-old. No problem, got this. Put them to bed, decide to watch Archer on their Netflix. Still good here. Something in the backyard. Being a strong, black, builded, independent woman, I decide to go survey the premises. So I go outside, realize it's just the apartment complex behind them. No big deal. Go back to watch Archer. Oh crap, the door's locked! In a blind panic, I ran back and forth between the front and back doors, attempting to open clearly locked barriers whilst vaulting their 6-ft fences. Around the third lap of freak-out, I discover there's a gate in the side. To call the parents out for their first date since spawn. So, fully out of breath, I try one more bright idea of banging on the ATO window, trying to wake her up. No avail, and the neighbor dog goes insane. End of story. Parents think it's hilarious and still bring up crying, mosquito-sweating me on their front porch, freaking out over being a negligent baby-watcher. Also, the 8-year-old may be traumatized by a stranger banging on her window late at night. Who knows?

I went to an NFL game and tailgated with a few friends. One friend brought a new girl he had been seeing—first time I met her. I'm drunk and talking to both of them, and I asked them if they're together. Evidently, they had yet to have that conversation, but they ended up having it on the walk into the stadium. I was invited to their wedding 3 years later. "Well, we were going to wait until after the game to announce it, but we are having a relationship."

Me and some guys met some girls on vacation. We hang out with them until two days later; they ditch us for another group of guys because they have weed. We're generally annoyed. Fast forward another couple of days; we're sitting by a campfire in town when another completely different group of guys we have never seen just randomly sit by the fire with us. We all just minded our own business because it was a public fire by a restaurant and figured they just want to stay warm. About five minutes later, we start a conversation with them. Turns out, they are the brothers of these girls that we met, and the girls we met lied about their age to us—told us they were 18; they were 14 freaking years old. We told the brothers they ditched us for weed. The brothers are pissed that their 14-year-old sisters are smoking with some other guys. We all decide to leave the fire together and go to Starbucks. Then bam, there we see the girls leaned up against a wall talking to the guys. All of us proceed past the guys and whisper in their ears, "They are 14 years old." The look on their face I will never forget—one of the most glorious moments of my entire life. Breckenridge, Colorado—no better place. That face is the one I make every day at work. I work next door to a high school at a grocery store, so those way too attractive to be 16-year-olds come into my store, and I feel awkward as all heck trying not to creep. I'm 20, and I still feel gross.

Second weekend at Giant College in the city as a freshman was incredibly daunting. It was really hard to find friends, and even if you did click with someone in one of the stupid orientation events, our school is so huge that unless you go balls out socially successful penguin and ask them to go to a movie or something with you 15 minutes after meeting them, you'll probably never see them again. So I'm thankfully in a class with a girl that I get along with well enough, and late in the week she asks if I want to come to her party—tea at a bar that had been rented out with her that weekend. Thankful to finally have been asked to do something with the prospect of making a real friend, I'm super excited about it. Sounds so lame now, but this college really is freaking huge, and I was so overwhelmed. Fast forward to Friday; I meet her at this bar. We have a great night, make some real friend headway. Suddenly, it's 3:00 a.m., and we decide to go home. My dorm is across the city via a really sketchy walk, and being the terrified friend that we were, neither of us thought me making that walk alone was a good idea. My new friend offers to let me stay in her dorm; her sweet mate is out for the weekend, so I have a bed to sleep in. We get back to her dorm, drunk and tired, and lo and behold, her crazy sweet mate has not only locked the door to her room but zipped the doorknob. It's a college dorm, so no couch. My new friend awkwardly asks if I want to sleep in her tiny, boss college twin bed with her. Keep in mind, we've had at most four conversations prior to this night, and I can tell she's hesitant to ask but also doesn't want to kick me out. I'm unfamiliar with the subway and don't want to walk back alone, so I agree, and we spend the entire night spooning in a tiny twin bed. We wake up the next morning to her roommate, who had barely conversed with her at this point, giving us extremely quizzical glances. Four years later and about to graduate, we were still living together, and she's become my best friend from college. I guess it's good, or else it would have made for a few weird changes in the hallway, and the roommate has also become a great friend. TL;DR Spooned with my best friend the first week of college before we were friends at all.

About five 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, "W" look. Apparently, this was the dinner when they were going to tell his parents about the engagement. We still laugh about that. You'd think your friend would have warned you; her boyfriend's parents didn't know yet. Glad they managed to see the funny side.

I was working out of town for the summer when my sister flew into 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 5 feet into the reception hall are we when I hear this squeal of delight. "Wedding Crasher!" cheered the bride. 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. 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 into walking into their wedding wearing a "Say No to Drugs" t-shirt and cut-off jeans. This is almost unbelievable. I don't believe that a bride like that exists. Come on, good turnout though, good timing.

I just remembered this story. 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 or whatever. I think it was the 720 club or something like that. Anyways, there's a buffet in there, so we're all getting food when a huge mob of men in suits walks in. My dad is shuffling over so quickly, I thought the floor might shoot sparks immediately. He bends down and tells my two older brothers and me to be on our best behavior because former President Jimmy Carter had walked into the room. He was a top graduate of West Point and works for Homeland Security, so he was able to talk to Mr. Carter for a few moments after we got our food and sat down. He walks 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." They shake hands, and he goes to stand next to my dad. I walk over with my mom and say, "Hello, Mr. President," while struggling to make eye contact, then proceed to hide behind my mom. I was, and still am, very shy at this point. My dad's face is split with a massive grin because of the pride of his well-behaved children, and in walks the middle child. He saunters up, sticks out his hand, and with the goofiest smile and loudest voice, my bro shouts, "Hi, you Jimmy!" My father's face turns from pure joy to horror in a blink of an eye. He could not believe that just came out of his mouth. Mr. Carter, along with the rest of his guards, is laughing now, and my dad looks so humiliated; I thought he might actually cry. The president just simply took my bro's hand, shook it, and said, "How are you doing, son?" He then just patted my dad on the back and said, "You did a fine job raising your family." After that, he walked over to his table with his guards and ate his meal. TL;DR My idiot middle brother tried to be casual with the president and humiliated my dad until the president told him he did a good job raising the family.

So my best friend from college randomly tagged along to my big family graduation party. This was a few states away. I'd invited a bunch of people, figuring no one would come, but she was free and said, "Why not?" Q forward a month, and she and my cousin (my extra big brother kind of cousin) have started dating and asks if I am really, actually okay with that. I say yes, 100%, absolutely, but of course, I would have to be maid of honor at their wedding (joking). Forward again, and they are, in fact, getting married. I get asked to be a bridesmaid. The only other bridesmaid is a lifelong friend of hers who lives on the other side of the country. I don't get asked specifically to be the maid of honor, so I figure I'm probably not, but the other person is far, far away, so I go bridesmaid shopping with her. Also being part of the groom's family, I throw her a shower; they ask me to give a speech at their wedding, etc. I don't know, I'm not the maid of honor, but I don't know if I am either, but I don't ask because it's a dang wedding; it's her lifelong friend, and she never asked, and my thought was based on a joke sent in a Facebook message three years earlier. I figured it'll come up at some point; I'll know. I don't want to ask and make it awkward. People keep asking me if I'm the maid of honor. I don't really know, but I guess it could go either way. I wrote two speeches: a maid of honor speech and a shorter, nice bride's family member speech. So we're running around the day before the wedding, and my mother asks if I know if I'm maid of honor. I say I still have no idea. Sure, maybe I should have asked a year ago when this all started, and I sure as crap can't ask now, but whatever, doesn't matter; not my wedding. I'll stand in line where they tell me to. Night before the wedding, my friend goes for a hair trial run, and I'm like, "Hey, I'll go with you." I walk in, chats with a woman, and goes, "And this is me, my maid of honor." Okay then, glad I wrote the long speech. Most of the family knows and thinks it's the funniest thing ever, but to this day my friend hasn't a clue. I can't wait for that perfect moment when I get to tell her because she will think it's the best thing ever to. TL;DR I found out I was the maid of honor 16 hours before the wedding; the bride still has no idea; I didn't know until then.

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, but they had been having a bad night or a fight, something like that, and heard me 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 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; to me, it 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.

I said to my best friend, "I was spending the 4th of July 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 their answers haphazardly, and he stood up, walked down the hall, and closed the door to 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.

Some time ago, I was reading about the legal age of consent, and somehow that led to me learning that it is 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 that last bit of information. It was extremely awkward that the rest of the students stared at me, but the professor gave me candy for knowing. This is actually about my sister-in-law. Edit: Clarification was asked for, so before you read: yes, we are lesbians.

My GF apparently went and bought an engagement ring for me and told her mom about it while they were out to lunch or something one day. Her mother seemed to think she had already proposed, even though my girl never said anything of the sort to her. A few days/weeks later, I get an email from her sister-in-law: "I just heard the amazing news! We are thrilled for you too!" Why? I was chatting with a friend at work and sent her the message saying, "What the f is this crazy talking about?" She called my GF and gave her the heads-up later that day. I called my GF and asked her; she played it off and made up an excuse about something she may have been overexcited about. I never gave it a second thought. Two weeks later, she proposed to me. Dang, good thing I am oblivious. The next time I saw Sil, she was super apologetic and was almost in tears because she thought she ruined the surprise. We are now engaged and hoping to get legally married on our 10th anniversary. Edit: Here is the proposal story. She was freaked out I was going to find the ring reaching in her purse because I was looking for her phone or gum or whatever. We were at a bar in the afternoon, and we walked down the dock to sit and look in at the water. She apparently had the ring in her hand, and it started sprinkling/raining. I said, "Crap, it is raining; let's go back." We sat back down with our drinks, and she just handed it to me. She told me she wanted to be with me forever, and she did start crying, which she never does. Then she called me a butthole for leaving the dock because it was sprinkling. She still loves me though.

One time, my friend's grandma died, so we wore all black and tried to look super fancy because we were pre-teens. I don't know. After the funeral, we went out to dinner at one of those chain restaurants because nothing pairs with crying quite like wordplay-themed appetizers. So we're sitting there, and our server comes up, and he's bursting with flair and bouncing everywhere and so ready to tell us about the specials that he's just going to explode with compliments. So he does: "Girls, you look super nice! Must be headed to a fun time; you're all dressed up! Got a big date? Big dance? Love it! Love dancing! You all look souped for a big night! Where's your dates? Going solo? Cute! So cute! Tell me about your big plans!" He's foaming with excitement. Here are a bunch of awkwardly dressed-up preteens, and he's like 20-something, and I bet he thinks we think he's so cute and charming, and my mom is probably going to give him a monster tip, but I'm 13 and I freaking hate everybody, so of course, I have to be the one that looks at him straight in the eyes in the most dead-panned voice I've got and say, "No, we just came from a funeral. Her grandma died." His face dropped so quickly that it was actually painful to watch. It was the most awkward moment I have ever created to date, and I am an awkward situation maestro. Never before had I witnessed someone actually stumble over their words out of sheer embarrassment. He was so flustered, he couldn't get out more than a couple of grumbles that sounded a little bit like "sorry," but more like "mmm g g g HR hdj," and then he just turned around and fled. Afterwards, we giggled like the horrible little creatures that are 13-year-old girls, but it was *th* fuckingly awkward for that guy. Poor guy. Also, our food was free, so that was awesome. Freak your potato skins.

Do you have a room for raping? Imagine yourself walking into a hotel at 2:00 a.m. in France where you unknowingly drop this gem of a question to the clerk. This absurdity can happen if the following circumstances hold: your last name is Violet, which in French is pronounced the same as "violer," a French verb meaning "to rape." In French, "Violet" and "violin" are homonyms. You are also so completely unaware of this serendipitous coincidence; your French is so underdeveloped, and your ego is so overdeveloped that you think you can pull off asking in a foreign language if the hotel has your reservation. In your head, you figure the best, simplest way to do so is to ask, "Do you have a reservation for Violet?" and then translate this real-time to "Avez-vous une chambre pour Violet?" Poor Violet. The clerk instead hears "Avez-vous une chambre pour violer," which translated back into English becomes the very first sentence in this comment. How does this story end other than informing your air quotes "friends" of your experience, and they decide to nickname you "The Rapist"? The hotel clerk may stare at you in disbelief while lifting up the phone to call the gendarmes for reinforcements. The coffee at a French police station is surprisingly good at 3:00 a.m. in the morning.

I once ruined a surprise wedding shower at the restaurant I worked for. I had no idea that it was a surprise. A bunch of ladies entered, claiming that they had a reservation for a wedding shower, and I seated them. Then two stragglers came in 10 minutes later, asking if a few women had come in earlier. I replied, "Oh, you mean for the wedding shower?" And one woman gave me death eyes while the other said, "Oh," (repeated many times). Then I gave them to another server so I wouldn't feel bad the rest of the night. The group should have told you; I would feel zero guilt if I were you.

My extreme lack of social life has led to many nights watching movie after movie on Netflix, one of which was a documentary on koalas. A few weeks after seeing said movie, I was meeting my friend at the deli where she worked, and they do a sort of "answer our trivia question of the day and win a free sandwich" thing. The question: "What species is fingerprints most similar to human beings?" I had been watching people come in and try and guess the answer for a good five minutes, only to fail and sadly shuffle away. My friend was busy closing her register, and this super chick in the sandwich line was talking to me about...

How stupid everyone else in the store must be, and how she thought it was so obvious. That is, until she got to the front and my friend told her she was wrong. So, with a chick still within earshot, I ask, "Is it a koala?" That is the only time my friend has ever made me a sandwich, but she said it was definitely worth it to see this chick fuming. TL;DR Koala fingerprints are most similar to those of humans.

I used to urinate in the vegetable patch. Six weeks later, my parents come over for dinner. They compliment me on how good the vegetables tasted. You read OP's heartwarming story, then you see this.

My friend—we'll call her S—was in college but came back home for the weekend. The college was a few hours away, so we didn't see each other often. Turns out, S invited a good friend she made at school to come down with her and see her hometown. When I came over, this quiet friend of hers—we'll call her M—was sitting in front of S's large living room TV with a PS2 controller in her hand, jamming some games. I, however, sat in the corner with S, trying to help her with one of her assignments.

Later, after the assignment was completed, I decided to attempt to get over my socially awkward penguin and try talking to this girl. I sit down next to her and ask her what she's playing.

M: "Um, Jack X racing."

Oh cool, I've never played it before. Mind if I play with you?

M: "Sure, but I've been playing this game for the last few weeks, so I may just stomp you into the ground."

Yeah, probably. I grab the second player controller, and we start. 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. I guess I thought that I wouldn't want her to go easy on me or something. I was sure that I blew my chance to get to know this very pretty girl better. We hardly talked the rest of the night.

A few days later, I'm sitting at my computer doing who knows what when I get a message. It's M. She got a hold of me through S. We end up chatting all night. We end up chatting all week. I end up getting her phone number, and we end up talking on the phone for hours on end. Nearly six years later, we are living together and living happily ever after. TL;DR Meet amazing girl, embarrass her, now living with her.

First semester at college, and I'm walking outside to go to Ultimate practice. A girl was looking around frantically. She knew my friend and asked if he could help her out. She needed to print out tickets for a Toby Keith concert that she had to leave for in 10 minutes. My friend said no, but I said yes. I'm a very shy, awkward kid who wouldn't think twice about talking to this girl. She's blonde and one of the more attractive girls on campus. I said maybe about two full sentences the entire time she used it, but apparently, that's all I needed to say. A few months later, and it's winter break. I liked something on her Facebook, and she ended up starting to talk to me. It turns out she has been attracted to me ever since that one day and never spoke up about it until then. We've been dating for about nine months, and every day is the best. TL;DR Helped a hot girl who needed to print something, ended up dating a few months later and still going quite strong. Summer, if you're reading this, you're the best.

I was Oak, but I wasn't the girlfriend, more of an overly attached stalker. So, I grew up with a guy who lived in a different town and adored him from the moment my young eyes met his. Over the next 13 or so years, I'd see him twice yearly. One year, I find out he has a girlfriend, and upon visiting, he is with her for a long time. So, I try to befriend him on RuneScape to no avail, and he is never home when I visit. Each year, I would become more and more frustrated and cry on the journey home. Fast forward a little, and 17-year-old Omi adds him on Facebook and comes clean about the obsession. Fast forward another year, and he, bless his heart, unblocked me after my whole teenage life, and by a complete stroke of luck, he wasn't yet deterred by my stalkerish ways. He took the three-hour train journey to visit me last July. I've since spent almost one and a half happy years with him, moved to his town, and I'm moving in with him in less than two weeks. Yay for me. TL;DR 18 years of persistence; talking doesn't always end in a restraining order. Don't encourage people.

I'm 12 hours late for this one, but here it is. When I was 17, I was pregnant and planning on giving the baby up for adoption. Everyone knew this and felt it was the right thing and tried to be supportive. At about eight 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 17 and not planning on keeping the baby. It had literally never occurred to me that having a baby could be nice. I was the youngest of seven and kind of hated babies. That drunken angel was the reason I kept my daughter. She is now 14 and incredibly awesome, and we have not only made it work, we have excelled at life, and I couldn't possibly be happier that someone's awkward gaffe changed my entire world forever.

I told my girlfriend that my nephew was getting a trampoline for Christmas. I spend all night building it, and she blew it by mentioning it out loud later on that night when one of the kids was around. It turned awesome because I still got to jump on it.

The girl I've been dating for a year or two—we met nine years ago when I was dating her roommate. The first thing she said to her roommate about me was, "Really, that guy?"

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 crap I was being. I deserved it. I was in my early 20s and a bit wild, but I knew I was being a crap, so I wasn't mad at anyone. 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—turned around, and went out before I started laughing. She and I broke up not long after, but that guy went on to be my best friend. Years later, I'm retelling the story of how we met and told his girlfriend that story. Turns out he'd been embarrassed about the incident for years. I thought he knew that I had never been mad, but he didn't and was really relieved.

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 a 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 learned so much and gained confidence to turn my talents into a real trade. I only hope everyone's life is graced with a good mentor, friend, whatever, to help empower them. If you are new to the channel, you can subscribe. I publish new videos every day. Until then, check another [Music] video [Music]. Bye for now.