Rory Hayden, as she was now going by since her grandfather had passes away grumbled to herself as she drove from Stars Hollow to Hartford. She'd never really bonded with anyone from Chilton, except for Paris during their time at Yale together, but for some reason she was driving to her 10 year high school reunion. She wasn't really 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 anywhere near her best day. She had temporarily moved back to Stars Hollow in her high school bed room, although still denying that she was home, her job prospects were grim and far between, and her love life was...well complicated to say the best. Since she'd run into Jess Mariano in New Jersey a year and a half ago they'd had this Vegas thing going, even though she thought she was over that when she had the same agreement with Logan all those years ago when they were still in Yale. She didn't know what the hell possessed her to suggest the arrangement; maybe it had something to do with always having a piece of Luke with her, who had died in a car accident along with her mother almost 3 years ago, and Luke had always been more like her father than her father had actually been, and another part of it was her feeling unsuccessful and lost in the world, especially after her grandfather had died, and needing something to anchor herself, but Jess couldn't be that person. Still, she clung to what they had all those years ago when they were 16 and in high school, and afraid of what her life would be like without him in it again.
The last thing that she wanted to do was to put on her fake society smile and schmooze with people who she didn't really like, but Emily had made it quite clear that she was expected to go, and Rory still had trouble going head to head with her. Unfortunately, not even Paris would be able to help her get through the night. Paris was in Chicago earlier that day presenting at a medical symposium on infertility treatments and surrogacy, when her water broke ending it immediately, and they had to bus her to the nearest hospital for her to have her and Doyle's daughter, who had still not made her appearance yet, and Paris fought with the paramedics the entire way to the hospital that she wanted to finish her presentation before she went to the hospital, they wouldn't let her. 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 those years ago, but she knew that the people inside could be just as bad. If she was going to survive this night would screaming, she needing 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. She had shut the door, when all of a sudden someone touched the small of her back, she let out a yelp! and jumped about a foot in the air, when she turned around before she heard the voice. "Ace?" She turned around to hug him, realizing that it was Logan. "Ace, why are you so jumpy? You're usually fine." He hugged me back. "Oh Logan, i'm fine, it's just being here and not really wanting to be here. Wait a minute, what are you doing here? You didn't go to High School here." He smiled at me. "I did my freshmen year and Sophomore year of high school, and i'm here as the guest speaker." Smiling back at him, I finally realized what was going on. "And before we walk in there, i'd like to reintroduce you to someone. Ace, Rory, you remember Colin, don't you? Well, this just became official yesterday, but we're engaged to be married next summer." I couldn't say anything, to say I was shocked was an understatement, never in my wildest dreams would I ever imagine Logan being gay, and especially not with his best friend. But years of Friday night dinners and events with Emily roped her into had prepared her for this. She steeled herself once more and walked through the doors, with Logan and Colin into her high school reunion.
Finn Dugrey ran his hand through his dark brown 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 wrecked havoc and made out with girls up against the lockers anymore. He was a grown mad, 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, as well as his best friends.
He had graduated Yale, surprisingly at the top of his class, and then went on to Stanford, and again graduated at the top of his class, especially when Logan wasn't there, although he missed his best friend dearly, and ever since he moved to London, with Mitchum's orders, he hadn't seen much of him in the last 6 years. He did meet up with Colin time and again, they were in Stanford together, and ever since Colin had met a new something or other they hadn't seen much of each other, either. He was now a Senior Partner at McCrae and Dugrey Associates. Colin's father had passed away shortly after they had joined the firm, and the two, along with Tristen Dugrey, who had rode along with him, 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 called Hayden and associates in order to secure their place at the post prestigious firm in the area.
Fin was grateful that he had changed since his high school and college 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 the only people who he kept in contact with from Yale were Colin, Logan and on occasion Robert, but he hadn't seen the amazing Rory Gilmore since her graduation day, when Logan proposed to her and was turned down. The one person who he had hoped to have kept in contact with since his Yale days was Rory, and she was the most difficult person to track down. If he could have one do-over in his life, it would be his relationship, or lack thereof, with Rory Gilmore. He met her the same time Logan did, and Logan had pretty much staked his claim on her away from everyone else, and no matter the times Logan hurt her over and over again, Fin stayed behind Logan, knowing he was in the wrong. He had been hung up on her since day one, and to this day 12 years after he met her, he still was. He knew she graduated from Chilton, and there was a big possibility of her being here, he just hoped he didn't walk in the room tonight with his cousin and find her happily married. Not that he didn't want her to be happy, because he desperately wanted to be the one making her happy. It would be far too reminiscent to seeing her with Logan after all these years, when he hadn't heard nothing from Logan in awhile.
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Tristan Dugrey ran his hand through his toussled blonde hair nervously as him and Fin pulled up in front of Chilton. He had once ruled these halls, a few years after Fin of course, but that didn't make him any less anxious about 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 entirely of his career, but he'd made his own way, and as a result he finally also repaired his relationships with his parents.
He had graduated from Stanford as the second to the top of his class, and then gone to Harvard Law, where he met Colin McCrae though his cousin Fin Dugrey. Colin had attended law school there as well, and they formed a fast friendship, aided by their link through Tristen's cousin, and Colin's best friend, Logan Huntzberger. He was now a Senior Partner at McCrae, Dugrey and Associates. Colin's father had passed away shortly after he and Finn had joined the firm, and the three 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, Hayden Associates in order to secure their place at the most prestigious firm in the area.
Tristen 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 enough about 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 15 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, just he wanted to be the one to make her happy. It would be far too reminiscent to seeing her with bag boy all those years ago.
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Tristen and Fin finally got out of the car, and made their way into the building, smiling appropriately and returning greetings as they passed old classmates in the hall. Yes, it appeared that some things never changed. Madeline and Louise both hit on them shortly after they walked through the door, despite the rather large and gaudy wedding rings that they were wearing. They just chuckled to themselves and brushed them off after giving an aloof greeting, wishing already that this night was over.
Tristen went one way to mingle with a group of guys he'd recognized, and Fin 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 playing tricks on 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 that got away. The only one had ever know the true identity of Mother was his grandfather, who had passed away several years ago. To everyone else, she was just a fictional character, someone who Fin talked about wistfully.
She was talking animatedly to a group of people, including his old partners in crime, Logan and Colin, and Stephanie and Robert had joined the group. She seemed happy. He couldn't hear from across the room, but she appeared to be captivating the group. They were all hanging on her every word. The younger 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 into putty. The only thing different about her she was sporting a very huge and pregnant belly. So, she had to be married, great, but Fin couldn't help but scan her left hand for a ring, and he couldn't see one but he didn't know if it was just too far away or not. He walked over to the group.
"Logan, Colin, how are you guys doing?" I started with them, and just talking to them, caused her to turn and look at me, and all I could do was smile at her as she gave me a hug. "Finny!" She threw her arms around me as best as she could with her belly. "Mother, you're looking great, and pregnant! Congratulations, who's the father, Logan?" Right after I asked Colin, and Logan spewed drinks over everybody causing Rory to excuse herself so she could clean up. "What are your problems tonight, guys?" I seen Logan and Colin exchange a few glances but no words were coming out.
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I walked out of the bathroom after cleaning spewed scotch off of me, when I bumped into someone. Looking up to excuse myself, and it was none other than...
"Tristen Dugrey!" She exclaimed happily. He smiled warmly back at her as he replied.
"Rory, Gilmore, as I life and breathe. Of all the joints in the world, you had to walk into mine."
"You finally got 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 besides, well never mind, 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 me?"
"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, when his cousin Fin had made a reappearance, when he went to introduce them. "Fin, this is Ma..."
"I see you met mother." Oh no
So who should Rory end up with at the end?
a.) Tristen
b.) Logan
c.) Fin
d.) Paris