Yale Male Affair


When Emily Gilmore finds out her granddaughter is friends with a married man, she throws a party. But Rory's selfishness knows no bounds, and the blond heir isn't impressed with her anyway. AU

Age Rating:

Chapter 1

"So do you know where Dad is tonight?" Lorelai cautiously asked her mother as the maid served the entrée. It looked like it might be snails.

"Belgium," Emily answered.

"For the waffles, right?"

"I have no idea what he went for."

"Well it was probably for business, but I'm sure he'll stay for the waffles."

Emily didn't bat an eye. "I'm sure we have much better things to talk about than him."

"Sure," Lorelai said slowly, taking the hint that her father was a sore subject for her mother. "Taylor wants to install nanny cams in everyone's house to watch for home invasions," she said. "He's really set on upping the security around town."

"Security systems are sensible, Lorelai," Emily said, inspecting her snails.

"Sure, when it's your choice. But Taylor wants to spy on everyone. We all left the town meeting with so many questions. Is he the one who's going to sit in a room full of televisions to watch everyone while we're at home? Will he keep the tapes so he can play back his favorite scenes?"

"Dean was telling me about that," Rory said. "He thinks Taylor might have finally come up with the scheme that will get him kicked out of his selectman post."

Lorelai scoffed. "No one can even remember when he was elected. Taylor put himself at the helm. He and he alone will decide when he's finished with us," she said. "I think it's all an elaborate social experiment."

When the maid came to clear away the plates, Rory excused herself to use the restroom before dessert was served.

"Dean?" Emily asked eagerly, leaning in towards her daughter when they were alone. "Dean who? Do I know his parents? Did Rory finally start dating someone from Yale?" She went on before Lorelai could answer, "I'm sure it took her a while to narrow down all the prospective suitors who were interested in her."

Lorelai's brows furrowed. "She isn't dating anyone from Yale. You remember Dean, from Stars Hollow."

"Oh," Emily said, frowning in disappointment and sitting back.

"And he's married, so she isn't dating him, either."

Emily's face registered mild horror. "Married? Dean is married now?"

"Yeah, he got married last fall, to Lindsay. She's a nice girl. Rory has a great story about her from a grade school field trip, where Lindsay is a Mark Twain coin hero," Lorelai rambled. "You should have Rory tell you about it, she tells it better."

"Why on earth is Rory talking to a married man?" Emily demanded. "And one she used to date?"

"It's just Dean, they're friends," Lorelai said with a shrug.

"Rory cannot be friends with a married man, Lorelai, it's completely inappropriate." Emily added, "You should have taught her better."

"Excuse me? They're just friends. And it's Rory, what do you think she's going to do?"

"She isn't going to sneak around having annual secret lunches with a married man while his wife sits at home, oblivious."

Lorelai softened. "Mom, Rory is not Pennilyn Lott—and Pennilyn Lott isn't even doing anything with Dad," she said gently. "It was just lunch."

"Behind my back," Emily said angrily. "And I don't know what he's doing over in that pool house. Do you know what it feels like to be betrayed like that by someone you trust?" She gave Lorelai a look. "Well of course you don't know."


"You need to put a stop to this immediately," Emily pressed. "Rory is obviously too young and naïve to realize what she's doing."

"She isn't doing anything," Lorelai said defensively. "There isn't anything to stop."


"They're throwing a party? Together? That's great," Rory said a few days later. "What kind of party?"

"Grandma says they're having over some of Grandpa's Yale alumni friends and want to know if you'd like to go—since you go to Yale too," Lorelai said, slightly stilted. "You do not have to go if you don't want to. I can give Grandma some excuse for you and we can do something else on Friday night. We can have a movie marathon."

"No, it's okay," Rory said. "I don't mind going to an alumni party." She checked her watch and started to get up from the kitchen table. "I have to go. I'm meeting Dean at Weston's. We're supposed to get coffee and pie. I think I'm going to get cherry."

"That sounds like fun. Hey," Lorelai said, keeping it cool, "what do you and Dean talk about these days?"
Rory frowned. "What do you mean?"

"I mean, back in high school you guys traded books and would flirt until you thought it was an appropriate time to make out."


"It was okay, you were dating. You don't have to pretend you didn't kiss your boyfriend when you were sixteen. I did a lot more than that when I was sixteen—you're the proof," Lorelai rambled. "So I was wondering what you guys talk about now."

"Just stuff," Rory said with a shrug. "School and books, like we used to."

"Yeah, but Dean isn't in school anymore. And he's always working, so he probably doesn't have a lot of free time to read."

"So I talk about school and he talks about work."

"Oh, I see," Lorelai said. She didn't let Rory go just yet. "What does Lindsay talk about?"

Rory was starting to get agitated with her mother. She frowned. "Lindsay?"

"Yeah, when you guys all get together at Weston's. What does Lindsay talk about?"

"Lindsay doesn't come along. It's just me and Dean."

Lorelai tiled her head and furrowed her brows, playing innocent. "Don't you think you should invite her? I'm sure she'd like to get out of the house for a while. She works hard, what with doing the laundry and making dinner every night before Dean gets home."

"I'm not really friends with Lindsay." Since her mother was looking so concerned, Rory added, "But maybe we could invite her next time. You're right, I'm sure she'd like to get out."

"That would be very nice of you," Lorelai said with a smile, placated by her daughter's endless generosity.


"It's a party with their friends who have sons," Rory complained into the phone in her grandfather's study. She was wearing a little black dress with what must have been the queen's jewels, and a tiara on her head. She was wearing a crown!

"I'm sorry, hon," Lorelai said. "I offered to get you out of it."

"I didn't think it was going to be this. It's so embarrassing," Rory said. "All these guys must think I'm pathetic or something, that I need my grandparents to introduce me to boys."

"They do not think you're pathetic. I'm sure after they met you there was no chance they could believe that about you. You're Rory." Lorelai asked, "Do you want me to come get you?"

"Aren't you on a date with Luke?"

"He won't mind."

"No, no. Stay with him. I'll figure something out." Rory ended the call and sighed. She exited the house, walking out to the back patio. She wondered if it was strange that her grandparents had a pool and she'd never gone swimming there. Kids liked pools, after all. But Rory had never been a normal kid.

She could hear music thumping from the pool house. She could see through the windows that some of the guys had formed their own party. It was rude of them to borrow the small house—likely without her grandparents' permission. Then again, they probably wouldn't have stopped anyone from borrowing the pool house. They didn't want anyone to know Richard lived in there.

Someone exited the little house then, an admittedly good looking boy with blond hair. He and Rory were 'introduced' earlier that night. It was unnecessary of course, as they already knew each other from school. He usually had a twinkle in his eye when he smiled, which was more of a smirk. It made him appear mischievous most of the time. He was one of those big-man-on-campus types, always with a girl in tow, and somehow everyone seemed to know him. Unlike all the other girls at school, Rory couldn't call herself a fan. She wouldn't doubt it if he was the one to start the pool house party.

He wasn't at Yale last year. Rory heard he had to repeat the eleventh grade as punishment for getting into big trouble at his extremely strict boarding school. Another rumor was that he took a year off to party and aimlessly globetrot. She wasn't sure which form of disregarding responsibility was true, but both stories sounded probable to her. He was clearly trouble.

He was, as all the other young men here tonight, someone her grandparents heartily approved of, by mere mention of his last name. One of his grandfathers did business with Richard since the beginning of time. Naturally. Everyone was such great friends. She supposed her grandparents didn't know about the trouble he'd gotten into. Or maybe they did but didn't care. It didn't seem to matter as long as he came from a 'good' family.

And he was from the jackpot of good families, one with a long line of newspaper owner-publishers. He was supposedly next in line to inherit the business. Richard and Emily were more thrilled about his presence than any of the other young men here tonight. He was an excellent connection, her grandparents giddily told her. The guy didn't even write for the Yale Daily News, what could he know about newspapers? She definitely didn't need his help getting a job after college.

Rory sat down in a patio chair and found a number on her phone to call. Luckily, she had a second choice since her mother wasn't available. "Dean, hi, it's me," she said when he picked up. "You will never believe this party at my grandparents'. I feel so stupid. I hate to ask you, but are you doing anything now?"

He wasn't. He'd be happy to pick her up. She smiled. She knew she could count on him, she always had been able to. She told him she was sitting in the back by the pool, so he wouldn't even have to go inside.

Rory sat in silence for a few minutes with her companion. She pulled a book out of her purse and opened it to find her place.

"Great party," the boy commented from his patio chair about ten feet away.

"Oh, yeah." She lifted her book slightly. "But at least I get to catch up on my reading."

He didn't give her a look of amusement that she was accustomed to when she revealed she'd rather read than engage in the perceived excitement around her. The corner of his mouth didn't lift, there was no look of wonder at her unique, though simple habit. He just barely nodded, his strong jaw set, his eyes lacking their usual twinkle. He turned his gaze to the sparkling ripples in the pool. It was a few minutes before he asked, "Did you notice you're the only girl here?"

"Yes. I'm sure that was a big disappointment for you."

He didn't acknowledge that comment, keeping the focus on her. "Why do you think they only invited guys?"

Rory still had her book open in her hand, but rested the spine on the table. "Knowing my grandparents, they were hoping to set me up with someone here. It's embarrassing," she said again. "I don't need them to find me a guy."

"Because you already have a boyfriend?" he asked. He gestured to the phone that was sitting on the table. "Isn't that who you were talking to just now?"

"No. It's Dean," she said. Her Dean. "We're friends."

"Good friends," the boy said. "He can drop everything to rescue the princess."

Rory wasn't sure if he was teasing her because of the tiara, but she didn't like his observations and questions either way. It wasn't his business who she was friends with. She was too annoyed to reply and returned to her book.

Headlights shined through the gate a while later. Rory looked up eagerly, closing her book and putting it in her purse with her phone. She got up to meet Dean just outside the gate when he got out of his truck.

"Hey, so what's going on?" he asked, glancing from the big house to the smaller one on the other side of the pool where the other party was in progress.

"Grandpa and Grandma are calling it an alumni party, but it's really a bunch of their friends who have sons around my age. They all go to Yale."

"Ah," Dean said, knowingly. She didn't need to tell him why they would do something like that, he already knew. He was intimately aware of their opinions on who was 'good enough' for her. It wasn't fair at all, of course. Dean worked so much harder than any of the boys her grandparents approved of. Boys like the newspaper heir behind her, who was more interested in a good time and notches on his bedpost than hard work. But he didn't have to. Greatness would be served to him on a silver platter.

Speaking of the blond, he walked over to the gate, just to the side of where Rory was standing. "How's the wife?" he asked, apparently noticing the band on Dean's left hand.

Dean frowned at the other boy without answering, and instead asked Rory, "What's this guy doing here?"

"I told you, it's my grandparents' party. I didn't invite him. I didn't invite any of them. I had no idea they'd all be here."

"Why are you getting defensive about a bunch of guys?" the other boy asked evenly. It was unnerving to have him there, just watching them like this.

"I'm not," Rory said, crossing her arms. She looked to Dean. "Let's get out of here. Do you want to get coffee?"

"Coffee sounds really good."

"Should I tell you grandparents you left with a friend of yours?" the blond called after her.

She glared back. "I don't care what you tell them."

Back in Stars Hollow, the house was empty. Lorelai must still be out with Luke, Rory thought. Or they went back to his apartment over the diner. Either way, she had the house to herself. It reminded her of another time her mother was out with a man all night, leaving Rory to do whatever she wanted. Dean had been so mad at her that night, and rightfully so. She couldn't go back, but she wished she hadn't made such a mistake. Dean was such a good boyfriend. He took care of her and she always felt safe. She could count on him, no matter what.

She looked up at him. If it was possible, he looked taller. His hair had grown out too, but other than small changes in physical appearance, he was the same. He was the same Dean she could rely on. He was her Dean.

She asked if he wanted a drink and he followed her to the kitchen. He glanced into her room and chuckled lightly.


He gestured to the room and took a small step in. "It looks the same. I guess some things don't change."

She gazed up at him, unable to agree more.

"Is it weird to come back here, since you really live in New Haven now?"

"Not really," she answered, brushing past him to get an inside view of her room. She could feel the electricity between them. It was the same as when they were in high school. But this wasn't high school. "Dean, where does Lindsay think you are right now?"

He shrugged. "She thinks I'm out."

"Yeah, but where?"

"Doesn't matter."

"What's going on with you?"

He looked down for a second, then sat his water glass down and took a step closer. "I can't make it work with Lindsay." Neither of them could, he explained. They tried, but he wasn't happy.

"I want you to be happy."

"I can be, again," he said, looking down at her intently.

She couldn't imagine him looking at anyone else like that. She took a step closer, and before she could register how it happened, she was in his arms, and they were as warm as she remembered. She tilted her head up until their lips were fused together and she was falling back on the bed.


Rory couldn't believe everyone knew. It was one time in her childhood bedroom, and somehow all of Stars Hollow knew about it. All of them. Taylor must have installed the cameras in everyone's houses without their permission, it was the only explanation she could come up with. She could feel people watch her and whisper about her when she walked down the street—minding her own business. She wasn't bothering any of them, and they'd stare at her like she was disgusting.

A couple days after she was with Dean, Lindsay had marched up to her in the front of Luke's, apparently having nothing better to do but wait for Rory, knowing she'd end up there at some point in the day. Lindsay said one word, "bitch," before slapping Rory in the face. She bitterly added, "I hate you." It was as though she didn't realize how unlucky she was to be in a marriage to a husband who still loved someone else. She was free now.

Luke had pulled Rory inside and took her upstairs, away from the gossipy town, who watched the entire episode with prying eyes and rapt attention. He did his best to comfort her, bringing her chocolate chip pancakes with whip cream, like it was her birthday. He didn't know what to say and barely made eye contact with her. It was nice of him, but she couldn't swallow down the hotcakes. It was like her throat was closed while tears burned at her eyes. It wasn't fair that people were treating her this way. They weren't what she would call perfect.

It was such a contentious topic that Taylor made everyone choose sides. There were red ribbons for Rory and yellow for Lindsay. That way people could avoid arguing in the street. Lindsay was winning by a hair, since people felt sorry for her. But others knew Rory was really the town favorite, and weren't afraid to point it out. They still remembered how cute she looked with Dean when they were sixteen. Miss Patty regaled the story of the time she found them sleeping in her studio the morning after the Chilton formal. Rory had looked so beautiful, sleeping in her pretty blue dress and running home on the snow dusted sidewalk in bare feet, like she was Cinderella. Babette cited Dean's loyalty to his first Stars Hollow girlfriend as proof that Lindsay was the interloper, not Rory. They conveniently forgot how her attention had strayed.

"Don't worry," her mother said. "They'll have something else to talk about in a few days. No one will even remember this."

Rory doubted it. The town lived for this kind of petty gossip.

Lorelai assured her that Richard and Emily would never know what happened. Rory was grateful, she would hate it if they thought less of her.

After a week of feeling like a leper, she had to get away from the small town. She took refuge back at school, keeping to her room when she wasn't in class or at the newspaper. Paris wanted to know why she was sulking, but Rory didn't want to deal with the judgment. She walked from class to class in a state of paranoia, sure that they all knew what she did, just like the citizens of Stars Hollow. It was silly, of course. She wasn't branded . . . she just felt like she was.


Rory and Dean were dating again. He and Lindsay were separated and would probably be legally divorced soon. It was an elephant that he didn't discuss with Rory. There wasn't much of a point. He used to be in a relationship, and now he was in a different one. It happened. They had a movie night with her mom and Luke. They ate a ton of junk food, and the tension between Dean and Luke was palpable. So all in all, it was just like the old days.

It was hard to find time and a place to be together. Dean had three jobs and lived with his parents, and Rory had classes and Paris for a roommate. There wasn't a good place to meet halfway between Stars Hollow and New Haven, so one of them would get stuck making the whole drive. It was harder for Dean since he was still sharing a vehicle with Lindsay. Rory didn't understand why Lindsay's parents didn't just get her a car if she needed to go somewhere. She didn't mention that to Dean, of course. She'd take whatever time she could get with him, but it would be nice if he was free more often.

Rory was walking out of class one day when she happened upon a room that housed one of the school's less prestigious campus publications. It was smaller than the newsroom the Daily Newsstaff worked in.

She saw the newspaper heir sitting at a desk set apart from the rest. He was leaning back in his chair with his feet up on the desk while he read something on a sheet of paper. He'd occasionally lower it to write something with a red pen. Once finished, he put his feet down and called over one of the reporters to discuss the article. He confidently made some suggestions, to which the reporter asked for clarification.

After he was finished, he noticed Rory standing by the door. "Can I help you?"

"Sorry, I was just passing by." She walked toward him, glancing around the modest newsroom and couldn't help but ask, "Why don't you write for the Yale Daily News?"

He shrugged. "I need to be able to run a newspaper. I didn't think competing for a by line at the flagship would be time well spent."

She bristled. "Don't you need to write too?"

"I do write." He lifted a full file folder with a vague description scribbled on the front. His brows scrunched up. "You do know the Daily News isn't the only paper on campus, right?"

She lifted her chin. "It's the only daily. And it's the top paper."

He quickly lifted a shoulder again. "Okay. Congratulations on being one of the chosen."

Like he wasn't chosen.

He turned to his computer, where his e-mail inbox was open. He read the message and made a note on his desk calendar for the upcoming Friday evening.

Rory's eyes widened when she saw the name of a well-known writer. She casually said, "Odd night for a book club meeting."

"My parents are throwing a dinner party." He nodded at his note. "That's just one of my mom's old colleagues from the Journal."

"Wow." He wasn't fazed. Was this the kind of company he always kept? "Lucky," she said. "I'd love a chance to talk with him—and your mom."

He shrugged. "They'll just laugh about inside jokes no one else will understand. I'll have to take a date so I don't get bored."

"It sounds amazing." Rory's heart beat quickened, slightly nervous at the prospect.

"How are things with Dean?" he asked suddenly, picking up some papers and sticking them in his file behind a Post-it marked 'color commentary'. He gestured toward her. "I've seen you around with him. Looks like you're together after all."

Her heart thumped and her stomach dropped in disappointment at his change of subject. "We are now. Things are fine, really good."

"Marriage didn't work out for him?"

Rory looked away. "No. They were too young." She didn't want him to think she had anything to do with it. They really were too young.

He didn't ask anything more. He had a cynical look in his eyes, not charming or mischievous. It was like he knew all the intricacies that made the world go round, and it was ugly. She felt like one of the ugly parts now.

In the spring, Rory heard about some girl showing up at that small campus paper, seeking out the publishing mogul. It was his ex-girlfriend from years ago, one he never got over no matter how many girls he dated. Some people thought it was romantic that they reconciled, but others—girls waiting in line—hated the girlfriend. She didn't seem to be anything special, Rory didn't understand why the blond boy was so hung up on her. He could do better if he wanted.

Things with Dean didn't work out—again. The relationship had been comfortable, like a trip down memory lane. When Rory tricked herself into ignoring the elephant, she was content. But only content. Being with Dean didn't make her happy anymore, and he must have sensed it, because just like before, he walked away. And like before, she didn't stop him.


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