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11 Times Situations Went from Awkward to Awesome

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Don’t you just love happy endings? How about happy endings to stories that start off on a really awkward note but then end with a (good) bang?!?

Take a look at these 11 stories from AskReddit users who share their stories of awkward situations that turned out really, really great.

1. Not a crook

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 ask her “Hey, did you steal your top?”

Turns out, those would be the first words I said to my best friend.

2. Happy ending!

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 ask 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 three years later.

3. A ruined surprise

My girlfriend 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 two!!! YAY!!!!!”

I was chatting with a friend at work and sent her the message saying “What is she talking about?” She called my girlfriend and gave her the heads up.

Later that day I called my girlfriend and asked her. She played it off and made up an excuse about something she may have been over excited about. I never gave it a second thought.

2 weeks later she proposed to me. Damn good thing I am oblivious!

The next time I saw sister-in-law 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.

4. “Or what?”

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.

5. Bridesmaid

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 “what?” look.

Apparently this was the dinner when they were going to tell his parents about the engagement.

We still laugh about that.

6. Recital

Played coed soccer when I was 10. Collided with 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.

7. First Kiss

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.

8. Wedding Crasher

I was working out of town for the summer when my sister flew in to a nearby city for her friend’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 Say No To Drugs t-shirt and cutoff jeans…

9. “Lack of social life”

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” things. The question: “What species has fingerprints most similar to human beings?” I had been watching people come in and try and guess the answer for a good 5 minutes only to fail and sadly shuffle away.

My friend was busy closing her register and this super mean-looking lady 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 the lady still in 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 lady fuming.

10. 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 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 walk 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 I to be on our best behavior because former President Jimmy Carter had walked in 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, ”Hiya Jimmy!”

My father’s face turns from pure joy to utter 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 are 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 pat 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.

11. Dorm room

Second weekend at giant college in 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 fifteen 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 a party 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 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 3AM and we decide to go home. My dorm is across the city via a really sketchy walk and being the terrified freshmen that we were, neither of us thought me making that walk alone was a good idea. New friend offers to let me stay in her dorm; her suite 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 suite mate has not only locked the door to her room, but ziptied the doorknob. It’s a college dorm, so no couch. New friend awkwardly asks if I want to sleep in her tiny 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.

Wake up the next morning to her roommate (who had barely conversed with her at this point) giving us extremely quizzical glances.

4 years later and about to graduate we’re 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 exchanges in the hallway. And the roommate has also become a great friend.