9 People Share The MOST Awkward Things That Happened On Their First Date

9 People Share The MOST Awkward Things That Happened On Their First Date

We’ve all had our “dinner at 8?” excitement. Everything about the first date is special. You’re both happy and nervous about the experience you’re about to have. You have butterflies fluttering in all possible directions. But imagine going to a fancy restaurant, all dolled up and thanks to your nervousness, you end up spilling something on your dress. Or maybe your date ends up saying something so awkward that you don’t know how to react. I hope it never happens but just imagine. It would be a day to remember and you’ll have a funny story to tell.

Here are confessions by 9 people about the most awkward things that happened on their first date!

This bittersweet combination of excitement and nervousness is weird yet hilarious and if you thought you were alone in this, you’re mistaken.

The one with the overprotective father!

“She had been talking about seeing The Amazing Spider-Man. So I thought, I am gonna take her there. She said yes to my amazement, but her father said no. That was a shot in my little self-esteem. Her father did not want his little girl going into a dark room with a pubescent boy. So, since I wanted to go out with this girl, I asked her father what he would allow. And he replied, and I swear these were his exact words “You may, boy, take my daughter to our front yard on a picnic with food I prepare. From ___ (time and day and all that).” Wow, that sounded like so much fun (sarcasm). But she said she wanted me to so it was set up.

The day arrived and I put on my nicest pair of jeans and a nice shirt and got in my mom's car and she drove me over there. I got out, walked up to the door, knocked and he opened it and said she will be out in one second. She came out and we sat in the grass and talked until he came out with sandwiches. I thanked him and he walked away. As we ate I turned to crack my back and I noticed the blinds of the upstairs window were wide open and there he was staring at me. The date was ruined. I was petrified. I think I said two more things to her and stared at the ground for the rest of the day. A half hour later, my mom showed up and I kid you not - that man was still in the window. As we stood up, she went in to give me a quick hug and I sprinted away. End of story.”

Source: Josh Oswald on Quora


The one who got stuck in an awkward family situation

“I don’t know if you can call this a date, I was 18 and I had my first car. I was waiting for my friend to hang out so I had the music playing loud. I’m at the city park and a limousine pulled up and outcome these girls, one has a wedding veil on and she comes to me and says, “I’m getting married tomorrow.” Her girlfriends are egging her on and she doesn’t know me, I never saw her before but she starts kissing me and grabbing me. She says let’s get in your car so I did, of course! Things happen and after like a half hour she leaves and her girls are laughing and high five her. The next day I’m in church attending my cousin's wedding, so I’m sitting on the end near the middle and as the bride is passing me I turned and looked. She glanced at me and we both said, “Oh my god!”. She kept walking and I totally put my head down and always tried to avoid family gathering.”

Source: Jimmy Palmisano on Quora

The one who was ‘too’ prepared

“My very first ‘first date’ I was 15 and naive. She was 19 and not. I don’t know how but I knew I was going to lose my virginity. So, I wore a condom. ON THE DATE. As I said, I was naive and too embarrassed about being a virgin to ask questions. When the moment came she reached down my pants only to discover that I was wearing a condom.”

Source: Jay Dee on Quora


The one who loved flying aeroplanes a bit too much

“The guy was an engineer with a passion for flying aeroplanes, so much so that he owned a house near the executive airport and a share of a small plane. For some reason, he told me that on the weekends he would start drinking at noon on Saturday and keep on drinking straight through the weekend until Sunday night. Immediately after that, he asked if I wanted to fly somewhere for dinner Saturday night. His voice trailed off as we both realized how bad that sounded. We just sat there as I realized this guy was not for me. I figured out some way to end it (it was just coffee) and got out of there.”

Source: Renee Wyman on Quora

The one who didn’t eat on the date

“I had a crush on this boy, I thought he was extremely attractive and when we planned for a date I was even more excited. He picked me up, we head to a restaurant and we started looking at the menu, he ordered for me but it is what I asked, so I had no problem with it. Then I ask, ‘Aren't you gonna eat too?’ and he's like, ‘I'm sooo full I can't eat.’ The food arrived and I started eating and he literally just stared at me the whole time and spoke to me a little but didn't eat. I thought it was so strange, he did this for the next two dates then by the third he got comfortable enough to eat around me but I still find it weird.”

Source: Dibora Kuma on Quora


The one who chose the wrong place to take their current date

“I went on a date with a beautiful lady at a local restaurant that was very popular in our area. We were having a good time and then the server comes up to our table and she says, ‘remember me you bastard?’ I turn around to see my ex-girlfriend Marie, who was working as a waiter at the establishment. Marie's face was fully red and she was angry that I was there with someone else. We had broken up a couple of weeks back and she was going to use this encounter as a chance to accuse me of cheating.”

Source: Gabriel Gallas on Quora

The one who faced an awkward situation on the first date

“Went to bar. Drank beer. Walked home. Put my arm around her, hesitantly because I was not sure yet. Walked through a park as we talked. Oh no! I had to pee. There is no proper toilet in the area.

I had to excuse myself and go behind a tree in the park in a city and relieve my bladder while she waited.

I ended up marrying her.

After that…. well….”

Source: Kevin Cameron on Quora


The one where chocolates were the problem

“We went to the movies. I was wearing a cute yellow tank top with a white mini skirt (this was the 80s). We’d ordered popcorn and a candy called ‘Snowcaps’ (they’re a dark chocolate candy with white sprinkles on them). Somehow, I managed to end up with several ‘Snowcaps’ on my seat. They melted on my nice white skirt making it look like I’d pooped myself!”

Source: Tessa Brown on Quora

The one where her little brother made the moment cuter

“Actually, it was my very first date, as in first date ever. He came to my door, rang the doorbell, and my sister let him in. As I was getting my coat, he stood in the front doorway. Just before we left, my little brother approached and asked him, ‘what are your intentions concerning my sister?’ I nearly died on the spot.”

Source: Laurie Woodward on Quora


How did your first date go? Do share with us in the comment section!

Also Read: 25 Easy & Engaging Questions To Ask *Him* On Your First Date and Ace The Art Of The First Date: Ways To Make Sure You Have A Blast!    

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