"Rory, it's your Grandmother, Emily, remember me? Well I am calling you to remind you that you agreed to go to the DAR Gala this weekend. I need to know if you have a date or if I am expected to arrange that for you as well. I have a dress being delivered to your dorms tomorrow. Wear it. Please call me as soon as possible and let me know if you have a date, young lady."
"Rory, your grandmother left you a message," Paris said walking out of her bedroom into the living area of their shared dorm. "Oh, it looks like you got it." she said, taking in Rory's pale face, standing beside the machine.
"I got it," Rory said with a sigh. "Did you hear it?"
"Yes, what are you going to do?"
"I don't know. I'm single. Can you think of anyone I could ask to go?" Rory asked, looking at her room mate with hope, Paris may be a lot of things but she is usually a good problem solver.
"Let me think, Glenn?"
"Nope, Grandma would spit him out in seconds."
"That guy she set you up with last year? Graham something?"
"Graham Sullivan? No, even that one night was too long."
"The single one in Lane's band, Brian?"
"Maybe, I think they have a gig this weekend though."
"Doyle?"
"Paper Doyle?"
"Do you know another one?"
"He is our boss, not a friend, and do you think I haven't seen how you look at him, you like him Paris."
"I do not. Oh how could I have forgotten him. Marty?"
"Marty, hmmm. That could actually work, I think he might be willing to go with me as friends, I'll call him."
"Just as friends?" Paris asked, she had seen how Marty looked at Rory, she knew he wouldn't be opposed to the idea of a proper date, he just was waiting for the opportunity to move out of the so called 'friend zone.'
"Yes, as friends, that's all we are Paris, you know that."
"Yeah but does he," Paris muttered under her breath.
"Did you say something?" Rory asked, while looking around for her cell.
"Nope, I'm just going to the library. I have an econ assignment due on Thursday. I'll see you later." Paris said, heading out the door.
"Okay, see you later. " Rory said, as she started to dial Marty's number on her cell. She started to tap her fingers on the counter as she listened to it ring, she really hoped he would answer, it would be much nicer to go to this thing with a friend instead of someone she had never even met before.
"Hello."
"Hey Marty, it's Rory," she said, in case he hadn't checked the caller id.
"Hey, what's up?"
"I was actually calling to ask you a favor if possible?"
"I'll help if I can, what is it?"
"Well, my Grandmother is hosting an event this weekend, and she has guilted me into attending, but I need a date. Are you free on Saturday night by any chance?"
"I am meant to bartend on Saturday night but I should be able to get out of it, if you would like me to." Marty asked, sounding almost excited down the phone line.
"Oh, well, if you have plans I can find someone else, I know how much you appreciate those bartending jobs."
"No really it's okay, I have worked for this person before, she doesn't exactly tip good and is a bit of a slave driver. I'll pass the job on to someone else."
"If you are sure, I would really appreciate it. Also, I don't suppose you have a suit?"
"A suit? Would a tux do?" Marty asked sarcastically.
"Do you have a tux? I assumed you wouldn't, but if you do it would be perfect actually." Rory said, having not caught the sarcasm in his tone.
"No, I don't. I have a black suit that I think still fits. Do I really need a suit?"
"Unfortunately, yes. Everyone will be in formal wear, just below black tie." Rory said apologetically.
"Okay, I can make that work. It's not like you set the dress code. I'll text you once I know for sure my shift is covered. Will that work?"
"Yep. That will be perfect. Thanks Marty, I really appreciate you doing this for me."
"Sure, no problem. I'll text you later."
Rory was just slipping her shoes on when Marty knocked on her door on Saturday night. Quickly checking her reflection in the mirror she rushed to open the door for him, she was pleased to see he had taken her advice and was wearing a black suit with a gray tie.
"Hey!" she exclaimed as she opened the door, "do you want to step in for a minute? I just need to grab a jacket."
"Sure, you look amazing Rory," Marty said, his voice sounding awed. He was looking her up and down as she walked towards the closet. She was wearing a violet a-line cocktail dress that ended just at her knees, with a generous but tasteful amount of cleavage visible with the sweetheart neckline, she looked spectacular, and he had to physically check that he wasn't drooling. "So where is this thing anyway?"
"The Club in Hartford." Rory answered, reappearing with her jacket on, fixing her hair over the collar.
"The Club? Oh the Country Club?" he tried to clarify.
"Yep, that's the one. Are you ready?" she asked, picking up her keys.
"Sure, how are we getting there? Can you drive in those shoes?"
"Oh, I'm not driving, Grandma sent a car, parking is atrocious at these things." Rory answered tonelessly, missing the look of shock flash across Marty's face as she was locking the door behind her. "It should be just in front of the building," she said, leading the way to the car park. "That should be us," she said, pointing at the black town car.
"Wow, I didn't expect this."
"Yeah, it's a bit much, but she really wanted me to come to this one, so she was removing all obstacles that I could use as an excuse," Rory said with an exasperated sigh.
"I'm sure it will be fine," Marty said, trying to reassure her.
"We'll see. At least you will be there, it should stop her matchmaking a bit, that woman is ruthless."
"Glad to be of help," he said with a smile, hoping he would be able to use tonight to convince her that he could be a proper date and not just a cover story.
Before they knew it they were exiting the car and walking up the carpeted entry to the club.
"Marty, I apologize in advance for anything at all that happens tonight." Rory said, earnestly as they walked through the club to the Rose Room.
"Rory, I am sure it will be fine, it's a party, really what's the worst that can happen."
"Well, don't say I didn't warn you," she said, before preparing herself to enter the room. As Marty watched she turned into a different person almost, straightening her posture, guarding her expression, and sticking a false mask of politeness on.
They hadn't even reached the bar after entering the room before they were set upon by the Gilmore matriarch.
"Rory! I am so happy to see you, don't you look delightful, wonderful choice of dress."
"Hello Grandma, you know I didn't have any choice in the dress," Rory said through forced teeth.
"I always did have fabulous taste. Now I am glad to see you looking so good, it seems like the only thing about tonight that is going well. I had one barman just not show up even though I requested his services weeks ago and he agreed. I'm telling you, he will struggle to find work in these circles again." Emily said, before looking again at Rory and suddenly seeing Marty beside her, she looked him up and down with pursed lips before speaking. "So Rory, is this your date? Introduce me please."
"Grandma, this is Marty and Marty this is my Grandmother Emily Gilmore." Rory said, introducing the couple.
"It's nice to meet you Emily," Marty said, his words prompting a gasp from Rory.
"That's Mrs Gilmore to you young man. Now Marty, am I to assume that is short for Martin? Do you have a last name?" Emily spoke, disdain dripping in her tone.
"It's just Marty Mrs Gilmore, not Martin, my surname is Wilcox." Marty answered nervously.
"Well then, Rory, you and Marty here may proceed to the bar and get a drink. Make sure you mingle dear, I have seen a few of your friends already this evening. I will see you later," Emily said, before giving them a final once over and walking away to greet some of the other new arrivals.
"That's your grandmother?" Marty asked in shock.
"Yep, I thought you met her before?" Rory asked, thinking back as they walked to the bar.
"Nope, just your grandfather. Rory I think I'm the barman that she was complaining about," he said sheepishly.
"But I thought you said you got someone else to work for you?"
"I couldn't find anyone, and then I figured that they don't pay that well anyway so I decided just to not show up," he said, with a shrug as they reached the bar.
"Martini please," Rory ordered, without even glancing at the barman.
"I'll have a beer," Marty ordered, only to receive a sharp look from Rory, he quickly changed his order to a scotch and soda.
"Sorry, but no one will be drinking beer, I'm actually shocked that they have any. I just wanted to minimize the reasons for Grandma to be angry."
"That's okay, I understand. I should have realized myself with the crowd that is here," Marty said, before turning to pick up their drinks from the server. "Oh hey Matt, how are you?" he asked, recognizing him.
"I'm good, I thought you were working tonight?"
"I got a better offer," Marty said, nudging his head in Rory's direction.
"Lucky, it was a good call, the battleax in charge of this one is awful, there will definitely not be free snacks at the end," Matt said, before moving on to his next patrons.
"Sorry about that," Marty began as they moved away from the bar.
"It's okay, Grandma's reputation is well earned, she goes through a maid a week." Rory spoke matter of factly, while glancing around the ballroom, trying to decide which direction to go.
"Your Grandmother has a maid?" Marty asked, starting to become aware of the difference in their socioeconomic class.
"Yes, she does. Mom and I always try to help them, but Grandma does have high standards," Rory said. "Let's go this way, I think I see some of the girls I went to school with, that should help ease you into this."
Marty looked around the ballroom properly for the first time, taking in the crowd, and more so, how easily Rory moved through it. She gave polite smiles to people she didn't know, arm squeezes and bright hellos to acquaintances, she fit in.
"Louise, Madeline!" Rory exclaimed, as they reached two younger couples.
"Rory!"
"Gilmore"
"I wasn't expecting to see you here, I didn't even know you were back in the area?" Rory asked, after she finished hugging the twosome.
"My father made me," Louise said, rolling her eyes, as the other two giggled. Robert was shocked to hear Rory giggle, he wasn't sure if he could remember her ever making that noise before.
"And well, you know me, I came along for the ride." Madeline said, before she turned her attention to Marty. "Now what have we here?"
"Yes, you aren't Dean?" Louise adds.
"Marty, I'd like you to meet Louise and Madeline, and their dates?" Rory began the introductions.
" Spencer," Louise answered.
"Eli," Madeline said. Their two dates simply raised their drinks as a hello, and went back to their conversations.
"Set ups?" Rory asked sympathetically.
"Yep, although they are kind of cute, I might take mine home to the pool house later," Madeline said. "Your's?"
"Oh, Marty is a friend of mine from Yale." Rory said, touching his arm in acknowledgement.
"Good way to escape the set up Gilmore," Louise said, eyeing Marty like he was a piece of meat. "I think I saw Paris just enter."
"No way, she told me she was going to visit Nanny tonight," Rory said.
"Yep, I wonder if she got ambushed," Madeline queried, as the trio watched Paris enter the room, on the arm of Graham Sullivan of all people.
"Is that Graham Sullivan?" Rory asked.
"I'm pretty sure it is," Louise answered, "Have you ever had the pleasure?"
"Really?" Rory asked, "I had the misfortune of one date with him last year, it was awful."
"The boy is dull, but he knows what to do with his tongue," Madeline said.
"Madeline!" Rory exclaimed, checking to make sure no one heard, as Marty choked on his drink.
"Gilmore, Grant, Lynn," Paris said, as she and her date reached the group.
"Paris, Graham," Rory acknowledged the duo. "I'm shocked to see you here Paris, we could have come together."
"Yes, well I got home and it was an ambush. I was not expecting to come at all. You know I spent the week mocking you for having to come. Marty, how are you surviving?" Paris asked.
"Hi Paris, it's okay, I could do with a fresh drink though. Rory?" Marty asked.
"Another martini would be great, thank you," Rory said, almost dismissively, as Marty walked away.
As Marty waited at the bar, he watched Rory with her friends. He was once again shocked that she looked like she fit. He had thought that Rory was more like him, scrimping and saving to make ends work while at Yale. She had definitely mentioned struggling for money growing up with a single mother, and Marty had met Lorelai, she wasn't a society person. So Marty was a little confused by this revelation. Shaking his head, he picked up their drinks and walked back over to rejoin the group.
"Thank you Marty," Rory said, taking her drink back. "We should probably do the rounds, I can sense Grandma's disapproval from here."
"Yep, she is looking over here, so you better get a move on," Paris said, with absolutely no sympathy.
"Okay, wish us luck, we will see you again later. Paris we have a car going back to Yale tonight if you need a ride."
"I'll keep that in mind, Gilmore," Paris answered, while giving Graham a side glance.
"So I will try and steer us towards normal people, but make sure we are seen talking to enough people that my Grandmother can't complain, if that's okay with you?" Rory asked Marty as they moved through the party.
"Sure, lead on, oh wise one," Marty replied with a laugh.
"I'm sorry, this hasn't been very fun for you so far. These nights unfortunately never are, especially the ones at the club. If they are in someone's house there is normally a sub party in the pool house, but when we are in the club there is nowhere to go."
"So you get dragged to these often?" Marty asked, having hoped this was maybe a rare occurrence.
"More often than I would like, more often around the holidays, and more since I started Yale, it's part of our deal for them paying my tuition," Rory said, glancing around. "Oh I see some people we should be able to talk to." Rory headed off, leading them in the direction of an older couple.
"Miss Gilmore! What a delight to see you again? How have you been?"
"I've been good, it's good to see you again as well, Headmaster Charleston, Mrs Charleston. This is a friend of mine from Yale, Marty Wilcox."
"Nice to meet you Mr Wilcox, and Miss Gilmore, I'm not your Headmaster anymore, remember." Headmaster Charleston said with a smile.
"I forget, I'm just so used to the title. How is everything going at Chilton?" Rory asked.
"Very well, this year's class isn't quite as ambitious as you and Miss Gellar were though. Do you know Miss Gellar, young man?"
"Yes sir, Paris is quite the force of nature." Marty said politely.
"That she is. Did Miss Gilmore here tell you she was Valedictorian? I thought Miss Gellar was going to kill me over it, she was quite disappointed. It is a wonder how they ended up such good friends."
"Forced proximity," Rory said, without skipping a beat, causing the group to laugh, while she thought about how serious she was. "Paris is actually here tonight as well sir."
"Is she? Well I will try to make sure I get to catch up with her. I always enjoy seeing how my students are doing, even if they are still in school."
"Well we better continue the rounds or else Grandma will have my head," Rory said, as though she was letting the elder couple in on a secret.
"Ah yes, if anyone is a force to be reckoned with it's Emily Gilmore. Okay, you youngsters have fun. And Miss Gilmore, I look forward to hearing about your successes in the future."
"Thank you Mr Charleston. Have a good evening," Rory said, taking Marty's arm, and steering him deeper into the crowd.
"Private school?" Marty asked, as Rory led him around, stopping to say hello occasionally.
"Yes? I thought I had mentioned that before?" Rory answered absentmindedly, looking for a safe place to stop and mingle.
"No, I don't think you did. Just that Paris and you had attended the same high school was all."
Rory looked at Marty trying to determine where he was going with this line of questioning. "We did, but I only transferred there sophomore year from Stars Hollow high."
"Rory? Rory Gilmore?" asked a blonde as they walked past.
"Yes?" Rory asked, confused as she was unable to place the face.
"It's Libby, from the DAR Debutante Ball? I see your escort didn't stick either," she said, eying Marty up. "Although this one is pretty hot also."
"Marty this is Libby, Libby this is my friend Marty." Rory said, making the necessary introductions while trying to place the girl, before remembering her as the drunk debutante who had sat beside her while they were getting ready.
"Nice to meet you Libby," Marty said warily.
"Nice to meet you too. So friend?" Libby asked, looking between the two to confirm the lack of relationship.
"Yep, friend."
"So Marty, what do you do?" Libby asked, her own date having wandered off a while ago.
"I'm at Yale with Rory."
"Yale? You must be smart then," she said, leaning closer and rubbing his arm.
"I can hold my own," he said. "Rory, I think your Grandfather is trying to get our attention."
"Where?" Rory asked, she couldn't see him from where she was standing.
"Over there, we should probably go and see what he wants. Nice to meet you Libby," Marty said, trying to escape the hansy woman.
"You just wanted to escape from her didn't you?" Rory asked, once they were away.
"Oh God yes." he said with relief, causing Rory to laugh.
"Sorry, I never see you with any girls so I wasn't sure if she would be your type or not." Rory said with a shrug.
"That is definitely not it," he said emphatically. "So how long do we have to stay at this thing?"
"Not too much longer, I think we have been seen by nearly everyone. We could maybe stop for tacos at Hectors on the way back?" Rory said, looking excited.
"Mary, is that you?" A voice called as they walked past.
"Nope," Rory said, "Keep walking," she whispered to Marty when he slowed down.
"Ah Mare, that hurts," the voice continues, only this time Rory turns to confirm the voice's identity.
"Tristan! I didn't see you there! What a shame, I also missed you," Rory said, in the most fake voice Marty had ever heard.
"That would be a tragedy." Tristan said, leaning in for a hug. Rory gave him a polite air kiss back, hyper aware that they were being watched by people around them.
"So they finally let you out of Military School?" Rory asked,
"Yes, I was allowed early release for good behavior."
"That must have been the lack of girls."
"You wound me. So how goes Harvard?" Tristan asked.
"I actually ended up at Yale, you?"
"Stamford, I almost picked Yale but then I heard that was Gellar's choice."
"I know, I'm her roommate,"
"Poor you, let me get you a drink in sympathy of that news." Tristan asked.
"No thanks. We were actually just about to leave, weren't we Marty?" Rory said with a smile. "I'm sure I will see you again in another two years when we cross paths at one of these things ET."
"No chance of your number then Mary?" Tristan said, as a last ditch attempt.
"Nope, see you around," Rory said, quickly pulling Marty away. "Sorry about him. I haven't seen him since Junior year, he was shipped off to Military School by his father."
"Really? I didn't think anyone actually did that?" Marty said, slightly horrified.
"Yep, it happened. So tacos?" Rory asked with a smile.
"Sure, will the car be ready for us?" Marty replied, excited to leave.
"It will only take a few minutes to come to the door."
"Then lead on," Marty said, gesturing for Rory to lead their way out of the ballroom.
An hour later, Marty was walking himself home after leaving Rory at her door, and contemplating everything he had learned that night. Sweet, innocent, small town Rory, that he had a crush on, was also private schooled, debutante, society party, trust fund kid Rory. He had realized when he met her Grandfather at the Yale Harvard game that he had sounded posh, but he honestly had thought he was one of those people who put airs on to seem of a higher standing than they are. Not that he actually was rich. How seamlessly Rory had fit in at the gala tonight had surprised him. Marty was beginning to realize that as much as he liked Rory, he would never fit into that kind of world. Marty had been the server at enough of those parties to know that he would never be able to blend in, not the way that Rory did. He thought back to how she smiled at the blonde idiot that she proclaimed to hate, she had never smiled for him like that. The more Marty thought over the interactions over the course of the night, the more his crush on Rory died. It was simply a pipe dream.