It Started on Christmas Eve

This is a story about 2 singles who started dating on Christmas Day, by chance. None of them knew this was going to happen. If you are still single and you have limited friends, it is time, to read this story and to re-think how you can make this Christmas different. Both Jimmy and Alison did not know each other. They were not being introduced by friends.

Jimmy was a workaholic banking officer, age 40 and still single. He had 3 past failed relationships and every festive season, he either stayed at home, or went shopping alone at the nearby shopping mall. His lifestyle was rather boring. He did not frequent night club, not a smoker or drinker. He was totally not a party person. He was tall for his age, rather fit but not a sweet talker.

Alison, worked as a marketing executive. She enjoyed meeting people. She was 35 years old then, a rather carefree person. Most of her friends were single and she was least worried not having attached. She registered to a few dating online platform but there was no one in particular she was interested. She was bubby and very much independent in her thoughts.

One week before Christmas, Jimmy’s colleague asked if he was interested to join them for a pool side party. “Hey, Jim, want to join us for pool side party?” His colleague asked.

As usual, Jimmy declined. On Christmas Eve, Jimmy left office and wandered along Orchard Road for window shopping. Feeling hungry, he went into a café and sat at one corner eating his dinner and watching people passed by. It was a luxury for him. A few table away sat Alison. She was happily waiting for her friends to come. She ordered some food and started tucking while waiting for her friends. A phone rang and she answered.

Christmas for single

‘I cannot make it today. My girlfriend just broke off with her bf and she needs me over. We catch up again.’ her friend said apologetically over the phone.

Feeling disappointed, she finished the food. She asked for the bill only to realise that she left her wallet at her office by accident. “Oh Shit,’ she mumbled. “It was so embarrassing.” She thought.

She reached out for her mobile only to know the battery went flat. Usually she bought her mobile charger but on that day, she left it in the office. Things were not right for her. Feeling frustrated and desperate, she looked around and saw Jimmy, sitting at one corner. Alison went over and asked if he could borrow his mobile phone.

Jimmy lent her the phone. Alison made several calls to her friends and colleagues hoping someone would come and pay the bill. No one answered. It was Christmas Eve. Feeling embarrassed, she asked if he could pay for her first and she paid him back the next day. Jimmy looked at the bill. It was not a lot and he paid. Alison took down Jimmy contact number. She went back to her office to get her wallet.


It was Christmas Day. Alison called up Jimmy who was at home watching TV. “Thanks for paying my bill yesterday. I got my wallet. Can I meet you for a drink and pay you back the meal?” Alison said on the phone.

Jimmy agreed and both met for a drink. As they chatted, they realised they were singles and they shared common interest. Alison found him a decent guy and being independent and outspoken, boldly suggested if he was okay to spend the day with her chatting and shopping with her. ‘Sure’ he said.

Indeed, they spent a day at Vivo city. Alison treated him dinner in return. After Christmas, they texted regularly on the phone and from friends, they started dating unknowingly. They are still together for 2 years now. Recalling back, they found it interesting on how they met on Christmas Eve, all by chance. Nothing was pre-planned and it worked out well for both of them.