"So who is this guy that you are taking as your date tomorrow?" Lorelai asked, as she joined Rory on the couch with a beer in one hand and a tub of Ben and Jerry's in the other.
"He is just someone I have been seeing for the past six weeks or so. I figured better the devil you know. We both know that one of the Grandmothers was working on a set up so I wanted to avoid that." Rory said with a sigh, looking at her Mom's ice-cream wondering if she should have grabbed a tub instead of the twizzlers she was currently eating.
"True, it is better for you, but does he know what he is getting into? A Hartford society party?"
"I don't know, but I know he has been to a few law board parties and things, so I am hoping that means he will know how to act."
"And what if he acts too good, and your Grandmother starts making commitment talk?" Lorelai asked, wiggling her eyebrows, knowing it was likely to happen.
"Then we stress the casual part of the operation? I don't know. He is okay but I know he is not a long term partner contender. There just isn't enough chemistry I think."
"Well, I hope you know what you are doing," Lorelai said, hitting play on the movie. "And, at least Luke and I get to meet him first."
"Yeah, about that, best behavior. Let Grandma traumatize him, not you," Rory said, only half joking.
"Hey, How was your drive?" Rory asked Theo as she greeted him with a kiss as he got out of the car after parking near Luke's.
"It was fine, usual Saturday traffic heading out of the city. Was that a giant rooster on the way into town?" Theo asked, looking skeptically around the small town square.
"Yep, that was Monty, he's been there forever. So are you hungry?" Rory asked, already leading him into the diner.
"I could eat, you said the food was good here, so I only grabbed a coffee from starbucks."
"Luke's coffee is THE best coffee ever," Rory said, leading Theo to a table, hoping that the amount of rubbernecker towns people around will be minimal.
"Hey Rory, who's this?" Luke asked as he appeared with menus.
"This is Theo, remember I mentioned him this morning. Theo this is my stepdad Luke Danes, Luke I'd like you to meet Theo Sloan."
"Nice to meet you sir," Theo said, standing and greeting Luke with a firm handshake.
"Nice to meet you too. Now do you both want coffee to start? Or do you know what you want?" Luke asked, looking at them.
"Yes, and I know what I want, but Theo might need time," Rory said, smiling at Luke, before looking uncertainly at Theo.
"Well, I haven't checked the menu, but I don't suppose you have any avocado eggs benedict on the menu? I just have a real craving for it," Theo said, as he looked at the menu, quickly realizing that the chances of the item were slim.
"No, we are more just normal diner food here, I'll give you a moment with the menu while I get your coffee," Luke said, giving Rory a look as he walked off.
"Sorry, that probably wasn't the best request then?" Theo asked, as he watched Luke march behind the counter.
"No, not really. You will like the french toast," Rory said, already knowing he won't pick anything too unhealthy from the menu. "My Mom's best friend is a chef at the Inn, where we will have breakfast tomorrow, she is more of an avocado toast kind of cook."
"Sounds good. I'll try the french toast then," Theo said, just as Luke approached the table with their coffee.
"Good choice, Rory?" Luke asked, having taken that as Theo's order.
"Blueberry pancakes please." Rory said, giving Luke an angelic smile.
"So am I meeting your Mom?" Theo asked, taking a sip of the coffee. "Oh that is good coffee, you were right."
"Mom had to work this morning, you will probably meet her when we go to check you into the Inn later."
"Okay, that will work. So what's the plan?" Theo asked, looking out the window at the small town, he was a born and bred New Yorker, and didn't know what to think of this place, where everyone seemed to know each other.
"Well, we will have breakfast here, although I suppose it's brunch now really, then I was going to take you on a tour around town. That will take us up to the time we need to get ready to leave for the Gala, it is in Hartford, at the country club. Okay?"
"Sure."
As they walked through the main room through the lobby Theo and Rory started to meet more people obviously heading to the same gala, but no one that they knew closely so they only required nods of acknowledgement not full greetings. They took a step into the ballroom and had a look around for people they knew.
"I see my Grandmother, I think she might be a nice easy place to start, and she just made eye contact so there is no avoiding her now," Rory said, gesturing to the left.
"I will follow your lead, you know this crowd better than I do," Theo answered her as they walked across the ballroom, passing groups of people milling around. "Wow, Rory, I recognise more people than I thought. Do you see that lady over there?" he asked, nudging his head in Francine's direction.
"Mrs Hayden? Yeah?"
"Can you introduce me? They are a big deal in the Law world, I don't know if you know that." he said, with a tone of almost awe.
"I'm pretty sure I can arrange that," Rory said as she continued leading him across the room.
"Hi Grandmother," Rory greeted Francine, giving her a quick hug and a kiss on the cheek before moving back to Theo's side. "This is Theo Sloan, my date for the evening, Theo this is my Grandmother, Francine Hayden."
"Nice to meet you, Mrs Hayden," Theo said, shock wearing off as he moved to shake her hand, which Francine graciously accepted.
"Francine, please Theo. No need to be so formal." Francine said, with a laugh as Theo looked at her in shock. "So Theo, what is it you do for a living? I am assuming that you are from New York?"
"I'm actually a corporate attorney for a firm in Manhattan."
"Oh, for one of the big firms, or for a smaller practice?" Francine asked curiously.
"Just for a smaller practice right now, I want to build up some experience and maybe eventually get on a partner track." Theo said, trying not to let his nerves show, he had no idea that Rory had so many connections.
"That's always the right idea young man, better to get some experience built up and learn your field. Where did you end up going to Law school? Rory here almost went to Harvard Law but she decided on publishing in the end."
"Grandmother!" Rory hissed, blushing.
"I never knew that," Theo said, looking at Rory with new fascination. "I went to NYU for both undergrad and Law School."
"That's a good school as well. Oh, I see the McCrae's I better go and say hello, Rory you should as well at some time tonight. And Rory, your father is around here somewhere, he escorted me tonight.`` With that Francine wandered off across the room to greet another couple.
"Drink?" Rory asked, as they watched Francine walk away.
"You're related to Francine Hayden? The Hayden's are your grandparents?" Theo asks in shock as soon as Francine is out of hearing range.
"Yes," Rory says with a loud sigh. "Can you keep it down? I don't need anyone to hear you!"
"How come you never mentioned it?"
"Why would I have? We haven't been dating for very long Theo, there are lots of things that I'm sure we both haven't mentioned yet. Can we talk about this later? People are looking, and I am meant to be mingling and representing the family."
"Sure, sorry, come on, let's get you a drink. Martini or red wine?" Theo asked, as they moved towards the bar.
"I think a regular gin martini," Rory answered, as they walked towards the bar. "It's safer for walking around a crowded room." Theo turned and ordered as Rory continued to survey the room. She could see lots of people she knew from the DAR, a few people she knew from Chilton, and unfortunately a couple of young men she recognised from previous set ups that Emily Gilmore had arranged.
"So is there anyone here that we must say hello to, or is it just whoever we bump into throughout the night?" Theo asked, as he turned towards her while waiting on the barman returning with their drinks.
"A few family business contacts, and some of the DAR members that are here, and running the event."
"You know members of the DAR?" Theo asked, looking shocked.
"Yep, I'm in the DAR." Rory answered while watching his reaction.
"What? You are soo young?"
"Anyone over 18 can join the DAR. I worked there for the summers when I was at Yale. To work in the office you have to be a member so I am a member, just not very active. They all know that I plan on working and never being a fulltime committee member."
"Wow, I'm learning so much about you tonight that I never knew."
"Okay, well we need to mingle, let's go and meet some easy people before we get caught by someone else again. Over there," Rory said, changing direction casually, "I see some people I went to school with."
"Miss Gilmore! What a delight to see you again? How have you been?" Headmaster Charleston said, stopping the couple as they passed.
"I've been good, it's good to see you again as well, Headmaster Charleston, Mrs Charleston. This is my date for the evening, Theo Sloan."
"Nice to meet you Mr Sloan, 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?"
"No sir, I haven't had the pleasure, but I have heard that Paris is quite the force of nature." Theo 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.
"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."
"Thank you Mr Charleston. Have a good evening," Rory said, taking Theo's arm, and steering him deeper into the crowd.
"Private school?" Theo asked, as Rory led him towards the younger crowd, stopping to say hello occasionally.
"Yes?" Rory answered absentmindedly, looking for a safe place to stop and mingle.
"I haven't been called young man since I was sixteen," Theo sniffed distastefully.
"Louise, Madeline!" Rory exclaimed, as they reached two younger couples, ignoring his last comment.
"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 us," Louise said, rolling her eyes, as the other two giggled. "You aren't normally here either."
"And well, you know me, I came along for the ride." Madeline said, before she turned her attention to Theo. "Now what have we here?"
"Yes, you aren't Dean?" Louise adds.
"Theo, I'd like you to meet Louise and Madeline, we attended Chilton together, and their dates?" Rory began the introductions.
"Husbands." Louise stated smugly, "Spencer."
"Eli," Madeline said. Their husbands simply raised their drinks as a hello, and went back to their conversations.
"Husband? I hadn't heard. Grandma isn't keeping up with her gossip, if I haven't heard about this. Congratulations." Rory said, embracing both girls again.
"We both got married last summer, Louise had a destination wedding in Hawaii, and I just had a smaller wedding on the Cape, you know how it is."
"Yes, sometimes you get so sick of the crowds at these things you don't want to see people, and if you claim it's a small family wedding less business associates need polite invites. I get it." Rory said with a smile, reassuring the girls she wasn't offended to not be invited.
"Oh I see my parents, you better run while you can," Madeline said quickly, almost pushing Rory and Theo along.
"Thanks, see you guys soon," Rory said, moving quickly.
"Hi Grandma, Grandpa." Rory said as she came up to her grandparents and gave them both a quick embrace. "Grandma, Grandpa, I'd like you to meet Theo Sloan. Theo, this is my Grandparents, Emily and Richard Gilmore."
"Nice to meet you Mr and Mrs Gilmore." Theo asked as he shook both their hands in greeting.
"Nice to meet you as well, Theo was it?" Richard asked, shaking his hand. "And what is it you do young man?"
"I'm a corporate attorney for a small firm in Manhattan," Theo led with while giving Emily a peck on the cheek in greeting.
"And how do you know Rory?" Emily asked, barely hiding the fact that she was looking him up and down, judging him by the tailoring of his suit.
"Grandma, Theo and I have been dating for the past month or so." Rory said, with a polite smile at her Grandmother.
"Oh how nice," Emily replied. "So you live in the city then, Theo? What was your last name? I didn't quite catch it."
"It's Sloan, Ma'am, and yes, I live right in the city, in SOHO." Theo answered with a bright smile, trying to be charming.
"Delightful."
"So Theo, do you golf?" Richard asked, trying to bring the meeting back onto friendlier terms.
"I do, not as often as I would like to with being in the city. But I do try to play virtual golf once a week at least, when I can't get out of the city to visit a proper green."
"Virtual golf?" Richard asked, sounding shocked by the idea, as though it was a crime against the spot.
"Yes, Grandpa. A lot of the executives at the firm do the same. There just aren't the same opportunities for a real game in the city." Rory interjected, she knew that Richard would know she meant the law firm, while Theo would think she meant the publishing company. "Anyway Grandma, Grandpa, I see Dad and I wanted to catch him before he left, you know how he likes to sneak out early from these things. Grandma, I will call you when I get home tomorrow."
"Nice to meet you, Mr and Mrs Gilmore," Theo said, with a smile, while looking relieved to be led away from them.
"So did you really see your Dad or did you just need an escape hatch?" Theo asked with a laugh.
"No, I really saw him, and he does tend to leave early, so it's better to grab him while you can," Rory said, with a genuine smile. "Dad!"
Theo watched as a man who appeared to be in his early forties, turned and smiled at the sound of Rory's voice. He wondered at how young he appeared before remembering meeting Rory's Mom earlier that day.
Rory had disappeared looking for her Mom, leaving Theo standing at the check in desk of this quaint little Inn for her to come back. As he was looking around, wondering what he had got himself into, especially after the tour of the weird town an attractive brunette appeared, a little older than his usual taste, but still hot, so he mentally prepared his charm offensive. He could already tell him and Rory wouldn't last too much longer, which was a shame as the sex was great.
"Hello, can I help you?" the brunette asked with a smile.
"I'm sure you can," he said with a smirk while looking her up and down. "The name is Sloan, Theo. I have a room booked for the night."
"Okay, I'll just have a look. What brings you to Stars Hollow?" she said with a polite smile.
"Oh, I just have an event to attend in Hartford, but I have heard wonderful things about this place, and its delightful staff, so I decided to stay here instead of in Hartford."
"You're welcome then. Thank you for giving us a chance. So just yourself?" she asked, pointedly looking around. "I see it's a king room booked."
"Well, I was just being hopeful that I would meet someone in this lovely town, and maybe hit it off and it could be the start of something special," he said, giving her what he thought was a seductive smile.
"I apologize sir, you seem to have a very different kind of establishment in mind, we-" she started off sounding indignant and beginning to get red in the face, as she was interrupted.
"Mom! There you are! I was looking all over, but then Sookie stopped me in the kitchen." Rory exclaimed, appearing from around the corner. "Oh good, I see you met Theo!"
"Mom?" Theo exclaimed, whispering to himself, "Oh shit!"
"Theo? This is your Theo? Your date for tonight?" Lorelai asked, again needing to clarify for her own mind.
"Yep," Rory answered, pulling her Mom in for a hug. "Did he not introduce himself? Or did you just get here?"
"Oh we had just started checking him in, you never gave me his full name last night so I didn't know they were the same person. So are you staying here tonight or coming home?" Lorelai asked Rory, while glancing at Theo who was doing everything he could to avoid eye contact with her.
"I hadn't decided yet, probably here, we will be home late and it will be easier. If that's okay with Theo that is?" Rory asked, looking at her date.
"Of course, you know you are always welcome by now," he answered, with a smile that just seemed lecherous to Lorelai, who now had to work out how to tell her daughter that her date was propositioning others.
"Theo, I'd like you to meet my father Christopher Hayden, Dad, this is Theo Sloan, he is my date for the evening," Rory said, her voice pulling Theo out of her head and back to the present.
"Nice to meet you, Sir," Theo said, going for a charm offensive, this man would be a good contact to have, the heir of the Hayden firm and fortune.
"Nice to meet you too, Rory, kiddo, I haven't seen you in ages!" Chris said, pulling her in for a hug.
"Dad, it's only been like a month. And I am in Boston this week." Rory replied with a laugh.
"Oh yeah I forgot about that. So Theo, what is it you do?" Chris asked politely.
"I'm a corporate attorney for a small firm in the city," he replied politely. "Just trying to get some experience and find a firm I fit in right now."
"Oh that sounds interesting," Chris answered, while Rory rolled her eyes, knowing her Dad found law far from interesting. "City Hartford, or New York?"
"Oh New York, in Manhattan."
"Do you enjoy it?"
"I enjoy the work Sir, I haven't quite decided about the firm. I might try to see if I can get into one of the bigger firms in a year or two." Theo said, in what he hoped was a politely charming tone.
"That's enough about work, so Dad, have you planned your escape from here yet?" Rory asked with a grin, being not at all subtle about trying to change the topic of conversation, as she realized Theo was trying to be opportunistic, while not realizing that her Dad was not the person to go to for an "in" with the Hayden firm.
A/N I am hopeful that the longer update will make up for the lack of frequency. I think once a week or so is what I am aiming for going forward.
