11 Times Situations Went from Awkward to Awesome

Photo Credit: Pixabay

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.