I am not affiliated with Gilmore Girls. *First fan fic, please be gentle with me :)

Rated M for language and [later] sexual content.

Chapter 1:

"Damn it!" Dean Forrester swore, his head bent over his new-to-him mustang. It was a bit older, but there was no reason in selling him a messed up car. Shaking his head, he backed up; tossing the tool he had been trying to use to tighten up a bolt at the engine. It bounced off and harmlessly hit the ground. He rolled his eyes and sat down on the curb in front of his parent's house. Living in Stars Hollow after everything that had happened seemed like a stupid move. He still couldn't believe he lived there himself. It wasn't that he didn't want to live somewhere else. He did. But he couldn't leave his hometown. The one time he had tried, he'd ended up on a five-day drinking binge and wound up in a detox center, being forced through AA. He didn't need that again; nor was he normally a drunk. It had been a horrible couple of years though. He forced a smile at the elderly couple watching him as they passed by. It wasn't their fault he was mad. He got back up, wiping the smudged grease from his hands onto his jeans. Oh well, he could buy new jeans.

It was kismet. There was no other explanation. There she was, walking across the road to Luke's. She had graduated college and gone off to this amazing job in New York or some big city. And yet here she was, in her sweats with her hair pulled up in a ponytail. Only Rory Gilmore could make frumpy look good. She glanced back, but Dean was only sneaking a peak at her. He'd gone back to "looking at his car". He didn't want her to think he was gawking at her. He only half smiled at the engine when he heard someone walking over.

"Hey there." She said, her voice sounding to Dean just like an angel.

"Hey Rory." He said with a smile on his face. His eyes searched hers as she looked back at him.

"Nice car." She said, inspecting the blue car. "The white stripes are a nice touch." She said, smiling a bit. Dean smiled back.

"I know, but the car itself isn't so nice. I am not exactly sure what's wrong with it." He admitted, rocking back on his heel. "But I'm sure you wouldn't want to hear about my theories."

She laughed and he caught his breath. "Well… you know me too well." She smirked, looking over towards Luke's. "I have to go meet my mom. But is there any way we could have lunch later? We could go to Al's Pancake World for some Chinese food…" She offered, her voice shaking just a bit as if she were nervous.

"Sure, I'd love that." He replied, shoving his hands into his pants pocket to hide the shaking.

She started walking away, looked back and said "Five thirty?" He nodded.

"Sure." He replied. She grinned once more at him and disappeared into Luke's.

I can't believe she wants to have dinner. Dean thought, after he showered a little while later. His hair was in dire need of a cut, but at least it wasn't too unruly. He tried to comb it but gave up as it curled outward. He hadn't ever cared too much about his hair; now wasn't really the time to worry about it. Dean headed out the door at 5:15; he lived just a block away from Al's but he needed to be just a bit early. Rory was a complete perfectionist; she was either right on time or early. She had never been late for anything like that except for the brief time she dated Jess. He felt a slight pang in his chest; even after all this time it still hurt to think about her and Jess. He shrugged it off. They had both grown up. Plus Rory had lost her virginity to Dean; Jess couldn't possibly hold a candle to him. Wait, could he? Dean thought, trying desperately to put these thoughts behind him as he walked. He entered Al's and found a seat by the window. The restaurant smelled horrible, because all of the mixed food smells. Dean laughed at himself and put the weird looking menu by the window. He already knew what they would order: Every single type of Chinese food that Al had.

Rory entered the restaurant and noticed Dean automatically. She moved over to him. Dean's heart was going crazy in his chest. He smiled and she smiled back. She leaned down and kissed his cheek, then took the seat across from him.

"Hi." She said. He replied with, "Hey beautiful." She blushed. "How have things been?" She asked, and he studied her face. He wasn't the type to lie, but he thought about it for a moment, and then went on with what he would say.

"Things haven't been too good. But things are looking up now." He meant because of Rory but it was true about everything else too. He had a new stable job as an architect's assistant, was back in school to be an architect. The owner of the company he worked for was paying for his schooling, that way they could go into business together. They had been friends for years and it seemed like a great thing. He was very excited and proud of this. He told Rory all this, but also told her some about the past.

"Things haven't been the easiest recently, mainly because after things happened with us, things went downhill. I quit eating, I quit living really." His voice was shaking, from raw emotion and from not knowing how she would react to what he was going to tell her. "I moved away for a bit, because I thought maybe it would help. But I also lost my family when I moved; none of them would talk to me. They all thought I was being stupid. Clara especially thought so." He bit his lip for a second. "I became an alcoholic. I lived away for a year. Give or take. I drank myself into a horrible depression. After drinking 5 or more days straight, my family came to make sure I was alive. And what they found wasn't much better. They saw that I was in horrible shape and forced me to go to Rehab. I spent 9 months in detox and learning better ways to cope with my issues. I have been almost a year sober." He said rather proudly at the end, but still felt like maybe she'd run now.

"Oh Dean, I'm so sorry." She said, biting her lip now. Dean could see that he'd upset her. That was the last thing he'd wanted to do; he hadn't told her for her to feel responsible or for her to pity him. He owed her the truth and not some sugar-coated bullshit.

"I'm sorry." He said, reaching out to touch her hand. She smiled a weak smile.

"I didn't realize things had been so tough for you. I'm in town for a similar reason. Not the alcoholic thing, but because I failed at something. I completely bombed out on my job. I don't even want to be a journalist anymore." She admitted, and Dean felt a pull of sadness for her. She must have been really confused and sad. "I didn't have it in me anymore. And so I moved back home. I know Stars Hollow doesn't hold too much for my future but I think I'm going to teach." She said a small smile on her face. "Four more years of school and I'll be a full time teacher. In the meantime, I have a job at the elementary school as a substitute. Also, they accepted my request to work part time as a librarian when I'm not subbing." She seemed more than thrilled at this prospect, and Dean felt genuinely happy for Rory.

"That's great!" He said. He could picture Rory working at a school. He couldn't exactly picture her with kindergarteners but maybe a little older.

As if on cue, Lindsey walked into Al's Pancake World. It was as if this was destined to be a road block; Lindsey never ate at Al's.

Dean ducked and whispered "I will be right back…" He glanced at Lindsey and ducked into the dinky bathroom. It was the last thing Dean needed; a confrontation with Lindsey in front of Rory; or for Lindsey to decide to confront Rory about her and Dean's indiscretion. He leaned up against the wall, more for support than anything. He texted Rory has she left yet? Rory replied a moment later with No. Dean frantically tried to calm his heart. This meeting with Rory was supposed to be a good thing. Not an all-out war. Is she getting a table or just take-out? He never got a reply back. He waited for a moment, but then peeked out the door. Lindsey was gone, but so was Rory. Dean cursed himself as he dropped his phone in his pocket and walked out the door. He looked around, finally spotting Rory's car. He walked towards it, but was only interrupted by Lindsey. He swore out loud, glancing at Lindsey.

"I have nothing to say Lindsey. Go away." He demanded, his voice very callous. It wasn't her fault; none of this was. That made everything so much harder. As Rory's car passed, Dean saw the mild look of hurt and alarm in her eyes. His heart dropped. Without a word to Lindsey, he walked back to his parents house.