The Dreaded Date – A Short Story

This short story is based on a writing prompt from

The prompt is as follows: Write about a first date that surprises both people, but in different ways.

The story:

Alice sat in the crowed bar waiting for her date to arrive. Her best friend had set this up for her because it have been over a year since the supposed love of her life and college sweetheart had broken up with her quite spectacularly on valentines day. Everyone thought that Alice needed to move on with her life (and more specifically her love life) but she didn’t feel ready for that. She had spent the first six months wallowing in self pity and over the following months she moved onto self hatred and self sabotage. This time last year she had a great career and lots of hobbies, he life was going somewhere. Now she was almost thirty and her life had completely stalled and everything she tried to do to make herself feel better just made her feel worse. She wasn’t ready to fall in love because she didn’t even feel like she loved herself right now. Despite these concerns here she was waiting for the man here best friend had set her up with, wondering if she had been stood up.

James was running late for the date that his friends had set up for him. The only thing he knew about the woman was how she looked (from the picture his friend sent him) and that according to his friends she was perfect for him. He wished that would be the case because he longed to fall in love. He wanted the whole thing, love at first sight and a fairy-tale happily ever after but the more dates he went on the further away love felt. The girls that he had dated had all been pretty and nice but ultimately the all important spark was missing. Over the last three years James had been on so many first dates that he was worried that he was starting to get the reputation of being a player. He knew this wasn’t the best impression for people to have of him but he wasn’t willing to give up on love and he wasn’t willing to settle for less than true love either.

He first laid eyes upon Alice from across the room, she sitting in one of the booths along the wall furthest from the entrance to he bar. She was looking down at the glass of wine in front of her, her eyes looked sad but she was still very beautiful with her long dark hair falling in waves down her back. Seeing her sitting there waiting to meet him made his heart sink slightly. As attractive as she undeniably was, he didn’t feel the instant love that he was hoping for. As he crossed the room towards her he resigned himself to yet another date with a beautiful woman who was not the one. He sat down at the table opposite her and he smiled in a way which he hoped didn’t betray his disappointment.

“Hi, I am James. It is a pleasure to meet you.” He said. She looked at him for a moment before she started to speak.

“You don’t know that yet.” She said. She had known he was attractive from his picture but she didn’t know anything about him. He seemed overly formal in the way that he was talking to her and the pessimist in her assumed that it was because he already hated her.

“Excuse me?” James replied, confused by her response.

“You don’t know me so how do you know it is a pleasure to meet me. I might be the most boring person you have ever met and by the end of the night you might be regretting agreeing to this date in the first place.” She said, smiling for the first time of the evening.

“I see your point, maybe I should plan an escape route just in case.” He joked, although he was thinking how this was already more interesting than half of the dates he had been on in the last six months. A smile crept across his face and Alice suddenly felt much more at ease. When she had first seen him approaching her table she had got the impression that he would have rather been anywhere else than there with her. Now, seeing his smile she felt confident and comfortable.

They spoke nonstop for the next few hours, they were so wrapped up in one anther that they only noticed how late it was getting when the bar was getting ready to close. They had talked about so many aspects of each others lives but more than that they had gotten to know each others personality and mannerisms as well. James had noticed the way in which Alice seemed to have a come back from everything and seemed to turn even the most serious of things into a joke. Alice had noticed the way in which James bit his lip when he was thinking.

They ended the together night with a short kiss before Alice jumped into the taxi that was already waiting for her. As she drove off into the night James realised two things. Firstly that he liked her. Even if he hadn’t fallen in love with her the second he saw her, there was definitely something there which could given time grow into something more. Secondly, he had almost not even given her a chance because of some preconceived idea on what love should be.

As Alice was taking off her make-up and getting ready for bed she realised to her surprise that she had forgotten to hate herself for the whole evening. The whole world seemed to somehow be brighter, as though the black hole that had been in her heart for the last year had been filled at least a little bit. She still wasn’t sure if she was ready to fall in love but she no longer felt so unworthy of it so when he text her the next day to propose a second date she agreed without hesitation.

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