AN: For those of you who have read my other stories and are cursing my name waiting for an update, I know you are probably asking why have I started a new story when I can't update my old ones regularly as it is? Well, I apologise and I can only tell you that I am seriously going to work on that. And this idea just popped into my head and I really like it. I had to write it down and I just wanted to post this first chapter to see what you all think and whether I should bother continuing. I value your opinions so let me know.

This is set three years after the show. Everything happened as it did on Gilmore Girls and of course this is a Rory and Logan based story. I still love these two and I'm just playing my part keeping the Sophies love alive.

Disclaimer: I don't own anything. I'm just borrowing the characters and having some fun.

The Life She Should've Had

Chapter One: Marriage and the Masochist.


She sat in the back seat of the cab, her fingers fidgeting with the clutch purse in her lap, her leg bouncing nervously and her mouth was bone dry. She had to keep reminding herself to breathe. She had to keep reminding herself why she was actually going through with this insane idea. It might have been three years since she had last seen him, but actually agreeing to be a guest at his wedding was just asking way too much of herself. Her life was a mess as it was right now; she didn't need to see what she could have had. She didn't need to be reminded of the life she could've had for herself, but turned down.

She remembered the moment she found out the 'good' news. While searching through The Hartford Courier for her article, she had stumbled across the smiling faces of one Logan Huntzberger and his blushing bride to be, Kim Masterson. They both radiated so much happiness in that little black and white picture. So much so that Rory had never submitted another piece to that newspaper again. Now as a freelance journalist, she couldn't really afford to turn down jobs but she wasn't a masochist.

Or maybe she was. In fact she absolutely must be because she was currently seated in the back of a cab on her way to the wedding of the year. The wedding of Logan Huntzberger, her ex-boyfriend and probable love of her life. She wasn't intending to ruin the big day. There would be no embarrassing declarations or desperate attempts to get the groom to change his mind and instead run away with her. As much as she still had strong feelings for Logan, she wasn't an idiot. He was getting married to someone who he clearly loved. He had moved on and despite the fact that he had invited her to his wedding, she was fairly certain that his invite held no ulterior motives. He was probably just being polite. Their families knew each other. It was simple etiquette. He absolutely did not still harbour feelings for her and he definitely was not trying to manoeuvre her back into his life. There was no way that he would do a 'Ross' and say the wrong name. He was just being polite and she was simply returning that politeness by attending.

She had talked herself out of attending Logan's wedding about a million times. Her mother had also tried to change her mind, but she truly was a glutton for punishment because here she was on her way to the church about to see the man, who three years earlier had asked her to marry him, say 'I do' to marrying someone else.

She just hoped that there was a lot of alcohol at the reception.

It would have been fine if her life had turned out the way she had wanted. She couldn't rave about how wonderful her job was. She didn't have the perfect guy in her life. She was still the same pathetic Rory Gilmore who worked as a freelance journalist, lived in a crummy apartment in Hartford and had no love life whatsoever despite her Grandmothers attempts to set her up. She was one of those pitiable people who peaked in college and the dreams that she had so vehemently chased were yet to come into fruition. Life was hard. It wasn't as wide open as she'd hoped. The years had wised her to the fact that not all dreams come true. And she was moments from watching another one crash to the ground.

Even after she had turned down Logan's proposal, she always had hoped deep down that they would find their way back to one another one day. Through all of the bad dates and the rejections, she had consoled herself with the knowledge that he was out there and that when the time was right they would end up together and live happily ever after. Today was the final nail in the coffin of that feeble hope. He hadn't felt the same way. He hadn't sat around waiting. He was getting married today to someone that wasn't her and she had to admit that a little piece of her heart was dying inside.

She wouldn't get to deliberate over whether she should take his surname or keep her own. She wouldn't get to meet those adorable blue-eyed, blonde-haired babies that her Grandparents had been so excited about when they first got together. She wouldn't get to spend the rest of her life with the most incredible man she had ever met. Someone else would. Kim Masterson would.

"We're here, Miss." The sound of the driver speaking snapped her from her soul destroying thoughts. She looked up and met the old man's gaze before craning her neck to the side to see the white building towering over her. It immediately filled her with dread. She felt like a vampire terrified of walking onto consecrated ground. What was she thinking? How could she possibly think that this was a good idea?

"Are you getting out or what?" She looked back to see the driver with a curious look on his face. She was pretty sure that he probably thought she was insane by now anyway. When she had first gotten into the cab she had taken about ten minutes to actually tell him where she wanted to go. Then when she'd finally worked up the nerve, she'd changed her mind and told him to take her somewhere else only to then change her mind back again.

"Oh right. Sorry," she mumbled and then remembered that she would need to pay the cab driver before she actually left the vehicle. She opened her purse and removed a couple of bills handing them through the gap. She tipped him healthily as a way to apologise for being such a pain in the ass.

As the cab driver started up his engine, signalling that he would now be leaving, Rory sat frozen on the seat, one hand on her purse, the other on the door handle. She nibbled on her lip as her heart thrummed in her ears. She internally screamed at herself to open the door and slowly but surely she did. She didn't glance back at the driver as she climbed out. She didn't need to see the look on his face. As she stood on the sidewalk, she took a deep breath and watched as the cab sped away from her.

Stupidly she waved as he left. She felt oddly attached to that nameless driver. Perhaps she could've asked him to accompany her to the wedding. She could say that he was her father, which of course would be ridiculous because Logan had already met her father and would instantly know she was lying and clearly insane.

"Oh my god, Rory?!" a high pitched voice called from behind her. Her feet were stuck to the sidewalk, not allowing her to turn around to face the direction of the voice. "Rory Gilmore, as I live and breathe."

Sighing, Rory turned to greet the oncoming blonde haired beauty. It took her a few moments to recognise the woman as the last time she had seen her she had been severely drunk, with longer hair and a tendency to want to make out with everyone. Now she seemed completely sober and her hair was still blonde only shorter. She drifted over towards her dressed in a beautiful baby pink designer dress that no doubt cost more than her apartment. She had a slight bump on her stomach, not from putting on weight. She was glowing and quite obviously several months pregnant.

"Stephanie?" she asked. She received a warm hug in reply.

"I can't believe you're here. You were the last person I thought would show up but here you are. I have to say, I think that's really brave. Oh and I love your dress. Is that Gucci?" Rory took a few seconds to recover from Stephanie's barrage. She always was so lively and bubbly and always cut straight to the point. She had been one of Logan's closest friends back in Yale and obviously they were still close.

"Um, no I got it on discount," Rory chose to respond to the safest subject; her dress was pretty plain and simple. A nice pale blue dress that accentuated all the important things and covered the rest.

"It's really pretty," Stephanie smiled, "It brings out your eyes."

"Thanks," Rory blushed. Even at the age of twenty-five she still blushed at the slightest compliment. "So when are you due?"

She tried to steer the conversation away from her and pointed towards the obvious bump under Stephanie's dress. The blonde frowned and placed her hands on her hips.

"What do you mean?" she said in a slightly insulted tone.

"The baby. When are you…?" she blanched when she saw Stephanie's eyes widen with rage. "Oh my God! I thought…"

Just as Rory was about to pray to the God's for some lightning to strike her down where she stood, Stephanie burst out laughing.

"Look at your face!" she pointed at her as she broke into hysterics. "I wish I had my camera."

Rory just stood awkwardly in front of her as people walked by. She stared in confusion before Stephanie finally managed to calm herself down.

"I love doing that to people. It's too easy," she beamed, pleased with herself. Realisation dawned for Rory and she couldn't help but scowl at the blonde.

"I'm due in October. Although, I really wish the little slugger would come early. Do you have any idea how uncomfortable it is being pregnant in this heat? I mean we're in Connecticut for crying out loud. Why does it have to be so hot?"

"Because it is God's soul purpose in life to piss you off, sweetie!" a deep voice addressed her. Rory's eyes widened as she caught sight of the owner of that voice. Colin wrapped his arms around Stephanie and kissed her neck. Steph rolled her eyes and then hugged him back. When Colin tore himself away from the apparent mother of his child to notice Rory standing before them, his face paled and his eyes widened in shock.


"Hey Colin. It's good to see you. Congratulations." Rory offered as Colin straightened up. She saw him steel furtive glances towards the church, clearly looking for someone.

"Thanks. You too." He nodded but he was obviously uncomfortable in her presence. "What are you…? I mean, who…?"

"She's here to stop the wedding!" Stephanie interrupted him. Colin's eyes widened further if that was at all possible and a look of sheer terror covered his features. Rory stared at Stephanie with a similar look of horror.

"I never said…"

"Oh my god, did you two lose your sense of humour or something? I was kidding. Geez what does it take for a pregnant woman to have some fun around here?" She shook her head and waddled away leaving Colin alone with Rory on the sidewalk feeling a million times more uncomfortable.

"So, you're not really here to…?"

"No," she cut him off vehemently. "I was invited."

Rory reached into her purse and brought out the invite to show him proof that she wasn't some crazy stalker, and that she was in fact a genuine member of the wedding party. Colin glanced at her and then at the invite.

"Oh." Colin remained stiff as a board as he lowered his gaze to his shiny black shoes. Rory began fidgeting with her clutch purse and biting her lower lip as the nerves began to take over her body.

"So, are you the best man?" Rory asked desperate to eradicate the horrible atmosphere between them. Once upon a time, Rory and Colin had actually been able to hold a conversation and not have it be awkward. She had even counted him as a relatively good friend. Things had changed drastically to the point where he could hardly even look her in the eye.

"Yeah, Finn was my best man. We agreed that I'd be Logan's," he explained and Rory understood. "Although, personally I think Logan got the better end of the deal. I mean, I have yet to sleep with any of the bridesmaids and I haven't lost the rings unlike a certain Australian."

Colin's brow furrowed as he remembered his own wedding and Rory couldn't help but giggle. Finn had always been the most unreliable person she had ever met so she could understand Colin's ire.

"So Finn hasn't changed much then?" she giggled and Colin shrugged it off.

"Listen the ceremony is gonna start in like, twenty minutes. The bride's not here yet but…" he hesitantly met her gaze, "…you should probably go inside and find a seat."

"Oh, right." She nodded and then took a deep breath as she walked around Colin and started heading for the church.

"Hey Rory?!" Colin called out to her and she spun back to face him. "It's really good to see you again."

He smiled a genuine smile and she mirrored his expression. She gave him a little wave and then continued on her journey.

As she got closer to the building, people were milling around, heading inside. She followed an old couple inside and then as her eyes darted around trying to figure out where she was supposed to go, she saw him.

Standing alone in his tuxedo with his eyes closed. He was taking deep breaths and muttering something to himself. Rory froze on the spot. It had been three long years since she had last seen him in the flesh. His engagement picture certainly didn't do him justice. Gone were the boyish good looks that had made him such a hit with the ladies back in in college. He looked so grown up. So different. He was handsome and he looked more manly. His blonde hair was slightly darker and still its usual disarray. Rory found herself smiling amused by that as she remembered all the times she had heard him cursing at his reflection when his hair wouldn't sit the way he wanted. Never mind the fact that he looked good anyway. She could just imagine him that morning battling with his unruly hair. Even on his wedding day it wouldn't co-operate.

It was his wedding day. Logan, her Logan was getting married. Only he wasn't her Logan anymore. That thought made her sigh in resignation and just in that moment, he opened his eyes and looked over in her direction. Rory's heart started thumping in her chest and she thought she was going to hyperventilate. Their eyes connected and for a second she was sure she saw him smile.


AN: So what do you think? Good? Bad? Indifferent? I know you want updates and I am working on them as we speak but please let me know what you think about this one.