I don't own Gilmore girls

A/N Warning, Warning this isn't going to be some fluffy gooey Jess falls at Rory's feet in adoration fic. This is going to be raw angsty and gritty. It's going to be a long up hill battle but in the end he's the Luke to her Lorelai so I have faith in them.

"Mom,"

"Yeah."

"I'm pregnant. "

"What?"

"Pregnant." She twisted her hands.

"It's Logan's baby."

"Isn't he getting married. didn't Paul just break up with you? My head is spinning."

"Yes to both. It's complicated."

"Okay Hun I need more details but right now we have a wedding to get ready for." She shook her head looking at her little girl not so little anymore seemingly destined to repeat her mistakes.

"Yeah you're right lets get this show on the road." With that the two Gilmore girls hurried to the inn to get Lorelai married. some vows and two flash mobs later Rory found herself looking across the square at Jess. She took a deep breath and sat down across from him.

"Champagne?" He held up the bottle

"I can't?"

"Why not? Going soft on me?"" she swallowed and looked at him. fear running through her veins.

I'm pregnant. It's Logan's baby and I don't know why I'm telling you this but I figured you deserved to know. "all the words rushed out of her like a title wave refusing to stop. A weight lifted and settled on her shoulders.

"Weren't you dating that Paul.. Peter. P guy?" Jess felt ill he felt like he'd been slapped here he'd been brooding about other things. Things that hurt but shouldn't matter. He didn't think he'd get something else to add to it. Something that would punch him the gut and have him down for the count.

"Yeah he broke up with me today."

Jess took the time to take in that information. "But then how?"

"Logan and me met in Germany a few years back he's getting married a French Heiress it was a what happens in Vegas stays in Vegas type thing only really London or Connecticut or Vermont or wherever we happened to land. She watched seeing emotion flash through his eyes.

He sat there stone cold silent. He couldn't move, couldn't think couldn't process. Who was this girl in front of him. and why was she telling him this it was like living in a very cruel world.

"Jess Say something." Rory pleaded looking at him. the shadow of the boy she loved at eighteen.

He scrubbed his hands over his face looking up at her. he refused to allow himself to fall into those ocean blue eyes. "What do you want me to say Rory?" He demanded. His voice harsh on the verge of breaking.

"Say something anything." Tears coated her words

He shook his head, took a deep breath huffed it out. Turned away from her. He bit his lip he couldn't look at her. "I…" He shook his head and went to stand up from the deserted town square.

"Please." She pleaded grabbing his arm stopping him. he turned and looked at her.

"God damn it Rory." He shouted whispered worried that the towns people were looking out their window which he figured they were. "Don't you ever learn. What are you nineteen again and sleeping with a married man." He hissed. "Twenty one and trying to get back at your boyfriend for cheating on you." He yanked his arm out of her hold and stalked off.

Rory felt like she'd been slapped. She could literally feel the physical pain of it on her cheek. She gasped a sob left her lips as she curled in on herself and held tightly to the table the edge biting into her hands. What had she done how had she ended up in this place? Thirty two and making the same mistakes her mother did at sixteen. And now Jess the one person who believed in her was disgusted by her. she could see it in his eyes hear it in his voice, in the words he'd spat at her.

"A fine mess you find yourself in Rory Gilmore." She muttered to herself standing up and trying to pull the wrinkle from her dress. She knew where he was going even if he didn't know and so she'd follow him.

"Stupid monkey suit." Jess growled yanking the tie from around his neck and pulling the coat off his shoulders. He wasn't sure how he'd ended up there but here he sat on the bridge. "Stupid bridge." He muttered throwing the offending garments to the ground and kicking off his shoes. He closed his eyes he wanted to scream. She was having Logan fucking Huntzberger's baby and to add to the mockery he was getting married to some French heiress. She always did go running back to him or to Dean but oh no Jess himself was never good enough for another chance." He shook his head.

"No use crying over spilled milk" Mariano. He muttered to himself. She made her choice and that choice led her to being a single mother to a playboy millionaire's baby. She'd been the mistress hell she'd been cheating on her boyfriend. P… Peter.. Paul whatever. "What have you done to yourself Rory Gilmore." He scowled looking into the murky water. He didn't know but what he did know is she'd made her bed and he wasn't going to fix it for her this time. he wasn't going to let her kick him and feel bad. It was time she looked fully in the mirror at herself.

He stood up his stocking feet snagging on the wooden bridge. He saw her coming long dress swishing against her legs and pulling him back so many years in the pass to another day near this bridge another bridesmaids dress. A younger him. a younger her.

"What." He snapped.

"Jess just listen." She pleaded.

"To what you slept with someone who was engaged, you had a boyfriend what more needs to be said Rory you're having his baby. What more needs to be said?" He was so tired bone tired.

"Why do you even care?" She spat back. "It's not like I cheated on you."

"Because you're better than this Lorelai Leigh you're better then someone who breaks up people who cheats who doesn't think of consequences. You're thirty two fucking years old. HAVE YOU LEARNED NOTHING?" By the end he was shouting his words whipping around them in the chilly fall air.

"How dare you." She poked him the chest. "You don't know anything about this about me."

"Give me a break. You jumped into bed with your ex playboy not caring who you hurt well good luck with that. Hopefully your child is smart enough not to follow in your footsteps. I wouldn't count on it though. You're thirty two and making worse mistakes then your sixteen year old mother."

"Oh give me a break my mother made worse mistakes when she was older than me." Or didn't you ever hear of her ill fated marriage to my father a few years back."

"Oh so it that your plan marry Logan? Oh wait but doesn't he have a fiancée?"

"Yes." Rory shivered the fall air whipping around her. "I mean no. I mean yes he has a fiancée no I'm not planning on marrying him. I don't even know what I'll tell him about the baby." Jess's jaw dropped. He sank to the boards of the bridge. Rory followed him.

She felt seventeen again. only she wasn't she was thirty two and she'd made a mess of her life. "Rory you have to tell him. This isn't fair. Give him a chance." Jess pleaded with her.

She snorted. "I never thought I'd see the day you'd stick up for a Huntzberger."

"Oh I still hate him don't get me wrong but don't do that your child. You know what it was like to grow up with a non existent father. Don't do it. Don't put your child in that position. You want them to have the Daddy's issues' you did. Maybe if Christopher had been around more. You wouldn't find yourself bed hopping and ruining life's now."

"Wow you sure do know how to paint me in a bad light don't you."

"No Rory you do that yourself." He stood up. "I can't clean up your mess Rory. I can't yell you into doing the right thing this time. it worked when you were twenty one but now you have a baby to consider. Make the right choices." He gathered his coat shoes and tie.

"Are we okay Jess?" she whispered.

"Not right now but we will be I think. I j Just wish…."

"You wish what?"

"I wish a lot of things, I wish you had been smarter. Had been the girl I know you can be. I wish I was thought more of then I am by you, by Lorelai by this town. I just wish things were different." His shoulders sank.

"What do you mean?"

"Really. So I'm sitting there in my stupid suit for Luke and what happens Michele comes up to me and says the wedding last night was better classier more elegant. And I'm looking at him like he's crazy as I say what wedding. And he precedes to tell me that Luke and Lorelai along with you Lane and himself snuck out last night and that Revered Skinner married them. so I'm sitting there at a fake wedding not even getting the curtesy of being invited to the real one. So that felt real good."

Rory's eyes widened. "I'm sorry, Jess. I.. we.. we didn't think I'm sorry about this all. She sniffed I guess I always run to you when it goes to hell and that's not fair so I'm sorry."

"Rory." It was the only thing he could say falling from his lips. A prayer. An admonishment everything he felt for her rolled up in one word. He turned leaving her on the bridge. He didn't look back as he walked away and she sat there frozen in that spot in time. she couldn't move couldn't blink as she watched his retreating back.

She pulled out her phone and dialed a familiar number. As the voice mail picked up she left a simple message. A simple message that was oh so complicated.

"Logan call me back it's important."

This was her mess she had to clean it up. She didn't' know where her life was taking her but it was time she really grew up she knew as she looked down at the murky water.