25 year old Lorelai Leigh Gilmore the third, aka Rory, was having a strange day. Today, February 14th, the day when millions of couples, had never been a particularly great day for Rory in the past, but this particular Valentine's Day had been amazing, mind blowing and surreal. She was still trying to grasp her head around the concept that now sat before her on her coffee table. Four identical black boxes. They all contained the same thing, although each one different. Four engagement rings from the four guys she had loved. The vibrating of her phone snapped her out of her funk and she scrambled across the room to reach it before it vibrated off the kitchen bench.
"Hello," she said breathlessly.
"Are you doing something naughty?" Lorelai asked suspiciously.
"To be doing something naughty, I would first have to have someone to do naughty things with," Rory replied as she took up her seat once again in front of the five black boxes.
"Not always," Lorelai replied without a hint of embarrassment in her voice.
"Thanks mom," Rory said scrunching up her nose.
"What's up kid? You told me to call you immediately," Lorelai questioned as she moved through the kitchen at the Dragonfly Inn.
"I have had the most surreal day on my entire life," Rory answered as she opened the lid on the first box and examined the contents.
"It all started when I arrived at the office this morning…"
Rory pushed open her office door effortless and squeal in surprise.
"Jess what are you doing here?" she asked as she clutched her chest and silently begged for her heart to return to normal beats.
"I came to see you. I hope that's alright?" he asked nervously, hopping from one foot to the other. Rory took a moment to look at her ex boyfriend.
'One of them,' she thought regrettably. Jess had matured. She could see it. His dark brown hair was now sitting above his ears and his once empty looking eyes were now twinkling with life.
"Of course it's alright," Rory said and hugged him awkwardly. "Please sit."
Jess sat in one of the plush arm chairs and watched as Rory hung up her coat and scarf and asked her secretary to bring in two coffees.
"So what do I owe this visit?" she asked as she took a seat on the opposite side of the desk and fired up her computer.
"Well its Valentine's Day and I know how much you hate them, so I was thinking maybe we could do something to change your mind," Jess answered. Rory gave him a strange look before logging into her profile on the newspaper system.
"What did you have in mind?" Rory asked, completely abandoning the computer and giving Jess her full attention.
"This," Jess said and pulled a small black box from his pocket and placed it on the desk in front of her. Rory's hands began to sweat as she realised what lay inside it. "I love you Rory Gilmore and I have since I first saw you in Stars Hollow. I know we haven't had the best relationship in the passed but I was hoping we could change that. Will you marry me Lorelai Gilmore?"
A loud gasp came from the doorway and both Jess and Rory looked up to find Emma, Rory's secretary, with two steaming cups of coffee, glancing from Jess to the engagement ring then to Rory.
"Oh my god," Rory said. "Are you serious?"
"Absolutely," Jess replied a small smile on his lips…
There was dead silence on the other end and Rory mentally counted to ten. She reached eight before her mother finally spoke.
"Jess proposed?" she asked calm yet Rory knew it was only the calm before the raging storm.
"Yes," Rory replied in a small voice.
"OH MY GOD," Lorelai yelled, scaring the workers in the kitchen. Sookie grabbed Lorelai and dragged her to a nearby bar stool.
"Mom, calm down," Rory tried to reason.
"You better not have said yes Lorelai Leigh Gilmore or I will disown you."
Silence followed that clear statement.
"Rory?" Lorelai asked, worried she had scared off her only daughter.
"I told him I would think about it," Rory finally answered. "But there's more."
Rory heard Lorelai take in a deep breath and ask for more coffee. Rory went onto explain her next marriage proposal.
As soon as Jess had left her office, Rory asked Emma to hold all her calls and change her meetings. She needed to get out and think, and the office was not the place for this kind of thinking. She found a quiet café, ordered a large coffee and settled onto the sofa.
"Mary, Mary quite contrary," someone leered in her ear and she clamped her eyes shut and groaned. This could not be happening. Not today.
"Hello Tristan," Rory said calmly.
"Rory," he replied and dropped a kiss on his ex-girlfriends cheek. "Don't you have work?"
"I could ask you the same thing," she retorted and took a long sip of her coffee. Rory had been surprised to discover that Tristan had been accepted to Yale. They had met at a Welcome to Yale party and after several weeks of pushing, Rory had finally agreed to go on a date with him. They had been together for eight months before their fighting tore them apart.
"The great thing about working for the boss is you can take any amount of time off," Tristan explained as he sat on the sofa opposite her. "I was actually on my way to your office."
Tristan grabbed something out of his jacket pocket and placed on the table in front of her. Rory gagged on the coffee before swallowing it. It induced a coughing fit that last for ten good minutes.
"Please tell me that isn't what I think it is," Rory begged and stared at the black box as if it was going to grow arms and attack her.
"We were good together Mare, and it sucks that our fighting broke us up. I love you and I want to marry you," Tristan replied with softness that Rory had only rarely glimpsed in their old relationship. It was that softness that melted Rory's heart and caused her to pick up the small box.
"I'll think about it and let you know," Rory replied before picking up the box and leaving the small café. She needed to go home where no one could find her.
"Bible boy? You've got to be kidding me. Two proposals in one day," Lorelai said her blue eyes wide with amazement. She glanced at her own engagement ring and wedding band and sighed with happiness.
"Try four," Rory replied and continued telling her story.
Slamming the front door closed, Rory nearly tripped over a vase of sunflowers sitting on the floor in front of her letterbox. She stamped her foot childishly and wondered if it was took immature to kick the flowers and leave them be. Sighing, she pulled the card from the flowers and opened it.
I know it's been awhile since we talked. Two years actually, but I was wondering if we could catch up. I know you detest Valentine's Day but there is something I really need to discuss with you. Meet me at 'our place' at 2.
Rory instinctively knew what he needed to discuss but she tried to push the feeling away. She headed upstairs to change from her work clothes and was pleasantly surprised to find Finn standing in her doorway.
"Finn," she called out and launched herself into his arms.
"Rory, love," he said and hugged her back.
"Come in," she instructed and opened the door to reveal a familiar and comforting place.
"I hope I'm not intruding," he commented as he followed her into the apartment. Rory shook her head and hugged him closely once again. Rory remembered their few weeks together and smiled. It was just after she had broken up with Tristan and Logan had just come onto the scene. Finn had made her laugh and they had a rebound relationship. Finn was still pining over Rosemary while Rory was trying to replace Tristan. Although it had only lasted several weeks, they had agreed to be friends. Rory still held a soft spot for the exotic Australian and knew that she had loved him in some romantic way.
"Your never and intrusion. What do I own this lovely and surprising visit?" Rory asked and a sense of déjà vu washed over her. She flicked on the switch to the coffee maker and turned towards Finn. She noticed it immediately.
"You've stopped drinking," she commented and Finn smiled widely at her.
"Been sober for almost two years now," Finn replied.
"Oh my god Finn, that's awesome," Rory said excitedly and hugged him for a third time.
"A few years ago I met this girl and without realising it, she made me see what life could be like without the alcohol. So I gave it up for her and I feel better about everything now," Finn explained as she accepted the mug of coffee Rory handed too him.
"She must have been an amazing girl to make you quit drinking," Rory answered encouragingly.
"She was. She is," Finn said.
"She's still in your life?" Rory enquired. "Tell me about her."
"You know her actually."
"It's not Steph is it because Colin will kick your ass if you try to take his girl?"
Finn chuckled but shook his head.
"Who is it Finn?"
Rory stared at him for the longest time.
"The day we broke up I knew that I had fallen in love with you. Then you got together with Logan and I knew I had lost my chance, so I figured that if stayed clean and sober and I might, one day, be worthy of your love," Finn explained and placed a familiar black box in front of her. "When I woke up this morning, I realised that I couldn't wait any longer. I bought this on my way over. I'm not expecting an answer straight away, but I want you to know that I love you Rory and I would do anything for you."
He stood up, kissed her cheek softly and left her apartment. This day was getting weirder and weirder.
"You never told me you dated the exotic," Lorelai cried after Rory finished telling her about Finn's proposal.
"Because it was a rebound thing. I never thought he actually loved me," Rory retorted as she stared at the ring Finn had given her. It was by far the most beautiful of the lot.
"And how do you feel about him?" Lorelai queried.
"I love him. There is no denying that. And what we had together was amazing but can I really marry him?"
"He gave up drinking for you. That's impressive," Lorelai continued. "I'm going to guess that Logan's was your fourth proposal?"
"Yes he was," Rory replied.
Seated at their table, Rory waited impatiently for Logan to appear. She knew what was going to happen at the end of this dinner and if a black box was going to be produced she wanted it over and done with as quickly as possible. It would be just like it was three years early. Before she had time to scan the menu, Logan walked in and he took Rory's breath away. She had forgotten how good he looked in a suit, and the way he carried himself with confidence had all the females and some males watching him as he passed through and took a seat opposite Rory. The familiar smirk was evident on his face.
"Hi Ace," he said and kissed her softly on the cheek.
"Hey Logan," she said shyly watched as he pulled his blackberry from his jacket pocket and placed it on the table.
"It's good to see you again," he commented, finally looking at her. He took in her shorter hair cut and guarded blue eyes.
"Can I ask you something?" she suddenly said, turning serious. Logan nodded. "Did you come here to propose?"
He stared at her like she was insane.
"Colin told you didn't he?" he finally asked and pulled her fourth black box from his jacket pocket and handed it to her.
"He didn't tell me a thing but apparently all my old boyfriends have a thing about proposing today," Rory mumbled but Logan caught every word.
"All of them?" Logan asked, his eyes filled with amazement.
"All except one," Rory replied. "Look Logan. I love you. I always will but right now I need to think about this."
Logan nodded in understand and then watched his ex-girlfriend leave the restaurant with his engagement ring with her.
"Well that was the least romantic of the lot," Lorelai commented dryly before turning serious. "So who are you going to pick?"
"I don't know, that's why I called you," Rory replied.
"Sorry kid. Only you can choose. I'll leave you too it," Lorelai said and after a last goodbye they hung up. Rory pulled her pen and pad from her coffee table and began to draw up a pro/con list for each engagement ring. This was going to be a long night.
OK so Im not sure who Im going to have Rory marry because I've always had a soft spot for Finn. So what I'm planning to do is set up a poll on my profile and have you guys choose. It will be up until Sunday night (Monday morning for me) so please vote. If I don't get any votes i'm going to place this in the one shot pile. Enjoy and plz plz plz vote.