Rory Gilmore grumbled to herself as she drove from Stars Hollow to Hartford. She'd never even really bonded with anyone from Chilton, save for Paris during their college years, but for some crazy reason she was driving to her high school alma mater for her 15 year reunion. She really was not in the mood for this. She didn't want to hang out with her old high school classmates even on her best day, and her life today certainly couldn't be classified as anywhere near her best day. She was temporarily back in Stars Hollow, although still denying that she was home, her job prospects were grim, and her love life was...complicated, at best. Since she'd run into Logan Huntzberger in Hamburg a year and a half ago they'd had this Vegas thing going. She didn't know what the hell possessed her to suggest that arrangement; she suspected that a large part of it was her feeling so unsuccessful and lost in the world and needing something to anchor herself, but Logan couldn't be that person. Still, she clung to what they had a decade ago for dear life, afraid of what her life would be without him.

The last thing that she wanted to do was to put on her fake society smile and schmooze with people who she didn't like, but Emily Gilmore had made it quite clear that she was expected to go, and Rory still had trouble going toe-to-toe with her grandmother. Unfortunately, not even Paris would be able to help her get through tonight. Paris was in Chicago presenting at a medical symposium on infertility treatments and surrogacy. The closer she got to Chilton, the more nervous she got. She finally threw in her Hep Alien CD and turned the music up, singing along to take her mind off of the evening ahead of her.

When she finally pulled into the Chilton parking lot she took a look around at the building she hadn't seen in so long. It didn't look as intimidating as it had all of those years ago, but she knew that the people inside it could still be just as bad. If she was going to survive this night without screaming, she needed to pull herself together. Regardless of how she felt, she had to appear to be every bit the successful woman that she wanted them to believe she was tonight, otherwise the Francies of Chilton Prep Academy would eat her alive. She stole a quick look in the rearview mirror, touching up her lipstick and checking her hair, before stepping out of her car. Despite how she felt, she knew she looked like she belonged here. Years of Friday night dinners and events that Emily Gilmore roped her into had prepared her for this. She steeled herself once more and walked through the doors into her high school reunion.

Tristan Dugrey sighed and ran his hand through his blonde hair nervously as he pulled up in front of Chilton. True, he had once ruled these halls, but that didn't make him any less anxious over tonight. He wasn't that boy who had wreaked havoc and made out with girls up against the lockers anymore. He was a grown man, and a success at that. He hadn't gone into the family business, unable to shackle himself to his father every day for the entirety of his career, but he'd made his own way, and as a result, he finally also had repaired his relationships with his parents.

He had graduated from Stanford at the top of his class and then gone to Harvard Law, where he met Colin McCrae. Colin had attended law school there as well, and they formed a fast friendship, aided by their link through Tristan's cousin and Colin's best friend, Logan Huntzberger. He was now a Senior Partner at McCrae & Associates. Colin's father had passed away shortly after he and Colin had joined the firm, and the two friends now ran one of the most successful law firms on the East Coast together. They were currently working to merge with another prominent law firm in order to secure their place at the post prestigious firm in the area.

Tristan was grateful that he had changed since his high school days of drinking, pranks, and womanizing, and he didn't want to walk through those doors and be expected to still be that person. He hadn't kept in contact with anyone from Chilton, and he thought that was a good thing. There had really only ever been one person in Chilton that he would have cared about enough to keep in touch with, but he hadn't ever actually made contact with her again after he'd told her he was leaving before Romeo and Juliet. If he could have one do-over in his life, it would be his relationship, or lack thereof, with Rory Gilmore. It was probably ridiculous that even fifteen years later he was still hung up on her, but that was his reality. He just hoped he didn't walk in the room tonight to find her happily married. Not that he didn't want her to be happy, because he desperately did. He just didn't want to see someone else making her happy. It would be far too reminiscent to seeing her with Bag Boy all those years ago.

He finally shook himself free of his thoughts and made his way into the building, smiling appropriately and returning greetings as he passed old classmates in the hall. Yes, it appeared that some things never changed. Madeline and Louise both hit on him shortly after he walked through the door, despite the rather large and gaudy weddings rings that they were wearing. Tristan just chuckled to himself and brushed them off after giving an aloof greeting, wishing already that this night was over.

He made his way over to the bar and ordered a scotch, and as he was waiting he couldn't help but wonder if perhaps his eyes were deceiving him. Standing across the room, looking as stunning as ever, was the one who got away. Of course, no one else knew that she was the one who got away. The only one who had ever known the true identity of Mary was his grandfather, who had passed away several years ago. To everyone else, she was just a fictional character, someone who Tristan talked about wistfully.

She was talking animatedly to a group of people, including his old partners in crime, Duncan and Bowman, and Madeline and Louise had also joined the group. He couldn't hear her from across the room, but she appeared to be captivating the group. They were all hanging on her every word. The 17-year old Rory Gilmore had been quiet and wanted to blend in, but the woman who was Rory Gilmore obviously possessed a confidence and could hold the attention of a group. He took in her physical appearance. She was breathtaking, frankly. Her blue eyes were piercing even from across the room. She had beautiful curves and a smile that he was certain could turn any man to putty. She didn't appear to be with anyone, but he couldn't see her hands well enough from where he was to see whether or not she was wearing a ring on her left ring finger. He quickly told himself to get a grip. He was starting to sound like a lovesick, angsty teenaged girl. He thought for a moment about crossing the room to say hello, but decided instead to hang back quietly and observe the room.

He had been immersed in pleasant conversation with an old classmate, his back turned to the bar, and he must have missed seeing her cross the room because he had no idea that she stood right behind him at the bar. At the sound of her voice he couldn't help but turn around.

"A martini with a twist, please," he heard her order from the bartender. He turned slowly to her, unsure of whether or not he should say something, but she quickly recognized him and spoke first. He didn't miss the look on her face when she saw him - surprise followed quickly by something that really looked like happiness.

"Tristan Dugrey!" she exclaimed happily. He smiled warmly back at her as he replied.

"Rory Gilmore, as I live and breathe. Of all the gin joints in all the towns in all the world, you had to walk into mine."

"You finally get the reference?" she asked happily.

"Of course I do. What self-respecting 32-year old man doesn't get that reference?"

"Well, obviously you weren't a self-respecting 17-year old, because you had no idea then," she teased.

"And obviously you're still quick with the wit and banter, Mary," he retorted.

"R-O-R-Y. The name's Rory, Dugrey. Learn it," she smirked.

"Oh, I know it well. If you'll recall, I used it not 90 seconds ago. I just prefer Mary."

"I'm going to let it slide this time, Bible Boy, because you're the most enjoyable person I've talked to since I got here, but don't go all testosterone-driven teenaged boy on me."

"It's a promise, Rory," he replied, emphasizing her actual name. "Now, what would you say to sitting down and catching up?"

"Lead the way. Mr. Dugrey," she replied with a broad smile. He placed his hand on the small of her back and led her over to a small table with only two chairs intentionally, hoping to discourage anyone else from trying to join them.

"So, Rory Gilmore, tell me all about your life," he said after he had pulled out her chair for her and then situated himself in the other chair.

"There's not much to tell, really. I graduated from Yale, where Paris and I were roommates, believe it or not, and then followed President Obama on the campaign trail. That was quite an experience. Since then I've done a little bit of everything. Life is a bit crazy now. I'm kind of...in between things. Such is the life of a freelance correspondent. I travel all the time, it seems. I spend a lot of time in London and some in New York City. I recently decided that it's stupid to pay for an apartment that I'm never in, so I finally moved my stuff back to my mom's in Stars Hollow, but I'm rarely there."

"I think that may be the most succinctly I've ever heard someone sum up over fifteen years of life, Mary," Tristan chuckled. "Surely there must be more?"

"No, not really. I threw everything into work, and here I am." Tristan took a deep breath and calmed himself before he asked the next question.

"That's it? No boyfriends, husbands, kids?"

"Kind of, no, and no," Rory replied sheepishly, thinking about her love life, if it could even be called that.

"How exactly does one kind of have a boyfriend, Mary?"

"It's...casual. Nothing serious. We see each other whenever we happen to be on the same continent, but we're not really...together," she answered awkwardly.

"That doesn't sound much like the Rory Gilmore that I knew," Tristan replied softly. Rory initially bristled at his statement, but one look in his eyes showed concern rather than judgement or criticism.

"If someone had told me that I'd be sitting here spilling my life story to Tristan Dugrey I would have told them that they were crazy," she mused.

"Look, Rory, I know that I was a real ass back in highschool, and I'm incredibly sorry for that. I've wished for fifteen years that I would have treated you better, but I can't go back and change it now. But seeing you here tonight...well, I'd really like to start fresh, maybe see if we can build a friendship or something."

"That sounds...well, really nice, actually. What do you say we get out of here, grab something to eat, and catch up? I really don't want to be pouring my heart out in front of half of Hartford society, but I really could use a friend."

"I say let's go. I know this great little hole-in-the-wall taco place near here, if you like tacos. We can grab takeout and go to my house and relax. I promise that I will be the epitome of a gentleman," he offered, standing and holding out his hand to her. She took his hand and followed him out to his car, finally excited for the night. They made a quick stop at the taco place Tristan had mentioned and then took them back to his house, settling on his couch after he'd made coffee.

"You look like you have a lot on your mind," he said as he watched her seem to get lost in her thoughts.

"I do. Maybe you can catch me up on your life first, and then we'll go from there."

"Sure. Military school was hell at first, but it was good for me. For the first time in my life, my last name and status didn't matter. I finally straightened out and graduated top of my class. I did pre-law at Stanford and then got my law degree from Harvard. I'm a senior partner at a prominent local firm now."

"And?" Rory asked.

"And frankly, that's really it. My life is pretty low-key and boring. I spend a lot more hours than I should in the office. My partner and I are working to merge with a couple of other firms in order to cement our place as the most prestigious law firm on the east coast. My parents are finally proud of me, and we actually have a good relationship now."

"Girlfriends, wives, kids?" she asked, mimicking his earlier questioning of her.

"No on all accounts. I mean, there have been girlfriends in the past, but not lately."

"You know, I never really hated you," Rory blurted out before she could realize what she was saying.

"No? Well, I certainly would have deserved it if you did. I really was an ass. I know I already apologized, but I want to make sure you know just how sorry I am."

"Why did you treat me like that?" she asked timidly. She noticed Tristan reaching up and rubbing the back of his neck.

"I liked you, Mare, a lot, and I didn't know how to handle that. I wasn't used to being turned down, and I wasn't used to actually caring either, and I just...I handled it all wrong."

"You liked me?" she exclaimed.

"Yeah, I did," he chuckled, amused at how shocked she was.

"Huh. I really never would have guessed."

"I can see that. Now, what's going on with you? I'm not that ass anymore, Rory, and I'd really like to be there for you. That spark seems to be missing."

"Tristan, I swear, if you breathe a word of this to anyone else I'll...well, I don't know what I'll do, but I'm certain that I'll never talk to you again."

"I promise, Rory."

"Alright. It's complicated, really. I don't know what's going on, to be honest. We lost my Grandpa, Richard, recently, and it's been so hard on all of us. I love my Grandpa so much, and losing him has left this huge hole in my life."

"I'm so sorry, Rory. Richard was a good man."

"He really was. We're all struggling with learning how to live without him in our lives. My career seems to be stalled at the moment. It's like...I can't get any traction. I'll think that something good is going to happen for me, but then it doesn't materialize. And it's not just that. I don't even know if I really want to pursue journalism anymore, but I don't know what else I would do. And that doesn't even begin to touch on my personal life."

"There's nothing wrong with making a course correction with your career, Rory. You're a fantastic writer; you were in high school, and I've read everything you've written since then and it's all been amazing as well."

"You've...you've read what I've written?" she asked.

"Yeah. This is embarrassing, but I have a Google alert set for your name," he replied sheepishly.

"You do?" Rory asked, wide-eyed in surprise.

"Yeah, I do. I wanted to keep up with you and see how you were doing."

"Wow. I'm a little shocked."

"I can see how that would be surprising, but if you're being honest with me then the least I can do is be honest with you too, right? So, what about your personal life is a mess?"

"That's such a long story I'm not even sure I could answer your question," she replied with a dry chuckle. "Frankly, it's embarrassing."

"More embarrassing than making out with random girls against your locker in order to try to get your attention and somehow convince you to date me?" he asked with raised eyebrows as he bumped her shoulder. She just laughed at him. "Yeah, I didn't think so. I've done some stupid shit, Rory, so I'm sure nothing you could say would surprise me."

"I met this guy at Yale. He was the epitome of everything I hated - rich, cocky, arrogant - and yet somehow, I fell for him. We dated for three years, and he proposed the day I graduated from Yale. I loved him so much, but I wasn't ready to get married. I needed time to find myself. I told him I couldn't right now, and he told me that it was now or never. He walked away from me that day. We hadn't spoken or seen each other until about a year and a half ago when we ran into each other in Hamburg, and we spent a week together. Now we see each other whenever we happen to be in the same place at the same time, but we're not exclusive. I know that I should let go and move on, but with everything spiraling out of control I guess I just feel like I need that one thing that's constant," Rory answered in true Gilmore run-on style.

Tristan saw the tears threatening to spill from her eyes and his heart broke for this woman who was sitting in front of him. He realized that while she may have looked the part of successful and in control tonight at the reunion, her reality was anything but, and he realized with startling clarity that he knew that feeling all too well.

"Rory, I want you to know that I understand what you're going through right now. My circumstances were of course different than yours, but what you've just described is my life before my father sent me off to military school. I was so lost and had no one on my side. Sure, I had people around me, but none of them actually cared for me. You were the only one who ever actually treated me like a person, that night on the piano bench, and frankly I didn't deserve your kindness, but you gave it anyway. But you, Rory Gilmore, deserve kindness, and you deserve more than to feel paralyzed by fear and unable to deal with your new reality. I've learned, from dealing with my own experiences, and if you'd let me, I would like to help you."

Rory took a moment to wipe the tears threatening to spill from her eyes before answering Tristan.

"Why would you do that? What's in it for you?" she asked timidly.

"What's in it for me is seeing that spark back in your eyes, Rory. I just want to see you truly happy and not struggling to keep your head above water."

"That's all you want?" she asked. She was no longer accustomed to people wanting to help her out of the goodness of their hearts. Other than her inner circle, it seemed everyone else always had ulterior motives.

"Well, I'd like to be able to stick around in your life even after you're all happily patched up and back to yourself," Tristan replied with a chuckle. "What do you say, Mary?"

Rory didn't have to think long to know what she wanted to do. She needed to find her way back to the Rory that she was proud to be.

"I say you're on, Bible Boy," she replied, a genuine smile on her face now.