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When Jess walked into the stately Hartford home, holding a vase of white lilies, he went unnoticed in the hustle and bustle of staff rushing around, soft crying coming from a room nearby, and the terrifying sound of Emily Gilmore shouting orders. He looked around, uncertain of where to find Rory or her mother—likely the only safe people to run into.
Standing in the empty foyer as the sounds filtered through the house of people grieving and planning, Jess texted Rory to let her know he had arrived. Before he left Stars Hollow, he had toyed with the idea of letting her know he was there from outside, but of course that was the old Jess. New!Jess had to go inside and face Rory’s miserable grandfather and horrifying grandmother.
She must have gotten his text because a minute later he heard Rory’s soft voice interrupt Emily’s, her grandmother’s exasperated response, and Rory’s footfalls on the hardwood floors as she came to greet him.
“Hey, Jess,” Rory greeting, leaning in to kiss him softly. He tried to remain calm as he heard the telltale sound of heels clacking as Emily Gilmore followed.
“Grandma, look, Jess brought flowers,” Rory said, taking his arm in solidarity.
“Marta!” she called, and a brunette woman ran in from an adjacent room. “Take the flowers from Rory’s thug boyfriend, please.”
“Mom!” Lorelai admonished her mother, coming into the foyer from the office where Richard could still be heard weeping. “Give Jess a chance. He did not have to bring you flowers. He did not even have to come inside.”
Rory tightened her arm around Jess’s waist, his arm loosely around her shoulders now that the vase was out of his hands. “My condolences, Mrs. Gilmore,” he offered sincerely.
“Yes, well, everyone’s very sorry. And Richard is inconsolable.”
“Well, mom, his mother died. Of course he’s inconsolable,” Lorelai replied in shock that she even had to say that.
Emily sighed audibly and conceded patronizingly, “Thank you, Jess. That was very thoughtful. I will tell Rory’s grandfather you brought them.”
Jess inclined his head slightly in acknowledgment.
There was a short pause as no one really knew what to say. Rory broke it by letting go of Jess to hug her grandmother. “Love you, grandma. I’ll see you on Friday for dinner.”
“You too, Rory. Thank you for coming to see your grandfather so quickly. I know he appreciated it.”
Rory nodded and smiled sadly.
“See you Friday, kid,” Lorelai said as she kissed Rory on the cheek.
“Oh, Jess,” Emily said as they turned to leave, “We would appreciate it if you would come to the funeral on Saturday. You are also welcome to attend dinner on Friday if you would like. Please let Marta know by Thursday either way.”
“Thank you, Mrs. Gilmore. I’ll have to check my schedule for Friday, but I will definitely be there on Saturday.”
“Very well. Drive safe.” Emily turned and walked into the study without any further dismissal.
Lorelai walked out the door with them and grabbed Jess and Rory’s elbows in excitement. “That was amazing! She didn’t even make a joke about your car accident.”
“You seem happy,” Jess commented.
“Hey, I’m just celebrating the lack of snark from Emily Gilmore. Whatever the circumstances, that’s a sheer miracle.” Lorelai’s smile didn’t quite reach her eyes, but Jess had to admit that he was pleased with how that Emily Gilmore interaction had gone.
“I’m sorry about your grandma,” Jess offered, the moment passing and the tone sobering.
“Thanks, Jess. It was really nice of you to bring the flowers.”
Embarrassed by the attention being heaped on him, Jess shook his head and looked into the distance. Rory smiled at her mother and said, “We’ll see you later, Mom.”
“Bye, hon.”
“Bye, Mom. Jess, would you mind driving back? I’m still not really feeling up to it.”
Jess nodded and opened the door for her, walking around to the driver’s side to take them both back to New Haven.
~
“So, that seemed…interesting,” Jess said, not sure what to say.
“Well, you know what they say about people grieving differently,” Rory said, not really sounding like herself.
There was an awkward silence, and then Rory reached over the armrest and took his hand in hers. “Thanks for coming to get me.”
“Well, I did have your car. I wasn’t about to steal it and strand you in Hartford.”
“You know what I mean. I told you that you could just text me and wait outside. You didn’t have to throw yourself at the Gilmores’ mercy like that."
“It worked out okay, though, don’t you think? I mean, I walked away only mildly concerned for my life.”
That got a bit of a laugh out of Rory, at least.
“Did you actually go into Doose’s to get those flowers? I’m surprised Taylor let you in.”
“No, I paid Kirk to get them for me. He took a 2% fee, talked himself down from a twenty.”
“You were going to pay Kirk $20 just to go into Doose’s for you?”
“Well, Luke was, in that the money wasn’t strictly from my wallet so much as from the cash register.”
“Ah, I knew you were acting too aboveboard. There had to be something else going on.”
“Don’t worry, the actual cash paid for the flowers was mine. Did you know that fresh flowers are ridiculously expensive?”
“I did, actually. You’d probably be better off stealing them from our yard in the future.”
“Is that allowed? I mean, I’m all for saving some money, but won’t Babette yell at me?”
“Of course she will, but that’s the risk you take for convenience. Just show that cute butt of yours and I’m sure she’ll get over it.”
“Nah, you don’t have lilies in your yard anyway, so it wouldn’t be worth it.”
“You know what kind of flowers you bought? You mean just didn’t just ask for sympathy flowers or random white ones? You actually chose lilies specifically.”
“Come on Gilmore, there’s this thing called the internet. I looked up what the appropriate flowers are to send for condolences. I figured Emily would notice if they were wrong, and I don’t want to be any more on her bad side then I already am."
“Well, either way, I’m super impressed.”
“That’s why you keep me around; my googling skills. It’s okay, I get it.”
“You know why I keep you around.”
“Well, I sort of know, but I don’t all-the-way know.”
“You know enough.”
“For now.”
“Jess!”
“What?”
“My great grandmother just died. I can’t believe we’re talking about sex when my great grandmother has just died!”
“Who’s talking about sex? I’m talking about why you keep me around, and how I’m not completely sure what that reason is.”
“You’re not so innocent, Mariano. I can read you like a book.”
“Wow, Gilmore, I’ve never heard that one before. Besides, neither of us has done much reading lately.”
A deep blush reddened Rory’s cheeks as she squeezed Jess’s hand.
~
Jess wore his best (only) blazer to dinner on Friday night. It was black and worn over a plain, clean, unwrinkled tee shirt with dark jeans. It made Jess look much more mature. Rory was impressed, but it was strange seeing him look so grown up when she was used to him as the anti-establishment layabout she knew and loved.
He picked Rory up with his car this time, driving them both to Hartford to meet up with Richard, Emily, and Lorelai for Friday Night Dinner. The funeral for Trix was the next day, and Rory wasn’t sure how the evening would go.
They pulled up to the Gilmore home and Jess said, “I can’t believe I’m voluntarily going into this house. Again."
“Honestly, I can’t either.”
“Don’t sell yourself short, Gilmore.”
Rory smiled.
“So, whenever you feel like we need to go, just put your hand up to your mouth and cough. That can be our signal for wanting to flee. I can’t promise anything, because Emily Gilmore will definitely insist we stay for each course and then after-dinner drinks, but I can always try.”
“That’s all I ask for.”
“You know I love you, right?” she asked.
“I’m aware,” he replied.
“Okay, then. Shall we?”
“I suppose we must.” They exited the car and Jess pulled a few things out of the trunk before they headed to the front door. The tension between the two of them was palpable, and neither was sure how to act in front of Lorelai, let alone Rory’s grandparents. Still, Rory seemed confident that Jess and Richard would get along much better than Jess and Emily. Or really, anyone and Emily.
So, here they were.
Marta had already been replaced, and a brand new maid apparently named Alessandra answered the door. Emily could be heard shouting directions for Alessandra to take their coats and see them into the parlor.
“I’m betting she’ll go through four more before this whole thing is done,” Lorelai offered conspiratorially.
“Mom!” Rory, stage-whispered. “There’s no way she’s that bad.” Then after a moment, she made her own wager. “Two, at the most. Alessandra might just pull through.”
Lorelai shook her head. “You don’t know Emily Gilmore like I do. When Aunt Cecile died, and I should mention how much both my mother and father hated her, Mom went through six maids. She’s gotten worse since then. I think four is a pretty conservative estimate.”
“There’s no way,” Jess protested. “She’s bad, but she can’t be that bad.”
“Oh, ho boy, am I gonna throw that comment in your face later.” Lorelai seemed sure in her estimation of her mother’s ability to go through maids, and she did know Emily Gilmore better than either of them.
“I’m out,” Jess said. “God, I hope I don’t have to see someone get fired tonight.”
“Same,” Rory agreed. “It’s very awkward to watch. Still, I bet two.”
“We’ll just see,” Lorelai whispered as they rounded the corner into the parlor. Richard was nowhere to be seen but Emily immediately spotted them.
“What took you so long?” she demanded. “And what were you three chattering about in the foyer? This is no time for your snark, Lorelai. I hope you haven’t been an even worse influence on Rory than usual.”
Under her breath, Rory could hear Lorelai mutter something about how she didn’t need to be a bad influence now that Jess was back. Thankfully, it seemed to have escaped Emily’s earshot.
“A drink, Lorelai?” Emily asked.
“Thank god,” she responded, and then at her mother’s look, “Whatever’s fine, Mom, thanks.”
“Very well. I’m having a glass of white wine. Will that do?”
“White wine’s perfect.”
“Wonderful. Rory, Jess, would you like soda? Water?”
Looking at Rory, Jess answered decisively, “Water, please, Mrs. Gilmore.”
“Me, too, Grandma.”
“Well that’s easy enough. Here you are, Lorelai. Would you please go fetch your father from his study? I don’t seem to have much luck getting him to join us.”
“Fine, Mom, although if you can’t get him to come out, I don’t see how I can.”
“I’ll try, Grandma, if it’s alright.”
“Oh, thank you, Rory. He might actually listen to you.”
Rory looked over at Jess, asking him silently if he wanted to stay with Lorelai and Emily or come with her. “I’ll help you,” he answered charitably, and held out a hand to help her off the couch. Leaving their drinks on the coffee table, the two headed towards the study where a grieving Richard waited.
Rory knocked on the heavy oak door, and heard the response from inside “Please leave me be, Emily. I’m not hungry.”
“It’s me, Grandpa,” Rory answered, opening the door hesitantly.
“Oh, Rory. You shouldn’t see me like this.”
“Grandpa, I’m so sorry. Mom and I are here if you decide to come out. Maybe we can help you take your mind off things.”
“Who’s that behind you?” Richard asked, distractedly looking at the figure half-hidden behind his granddaughter.
“Oh, grandpa, this is Jess, my boyfriend.”
“Ah, yes, I’ve heard quite a bit about you.”
Jess stepped out of the shadows and walked over to Richard, reaching out a hand to shake. “I hope you don’t take it all to heart, sir.”
“Yes, well, I’ll make my own judgments.”
“This is for you, Mr. Gilmore,” Jess said, pulling out a hardcover copy of Walden. “It’s not a first edition or anything, but it’s in good condition and it is from an early printing.”
“Well, now, that’s quite a nice thought,” Richard said charitably.
“I’m sure you have a better copy in your own library,” Jess demurred. “Rory says you have tons of first-editions.”
“Well, yes, I do. But one can never have too many books. Especially Thoreau.”
“You didn’t tell me you brought that for him,” Rory whispered, pulling Jess aside. “That must have been expensive. You didn’t have to do that.”
“I’ve had it a while,” Jess replied. “Been waiting for the right person to give it to, I guess.”
“What other surprise books do you have in the wings, mister?” Rory asked teasingly.
“You’ll just have to wait and see,” he smiled.
They both turned back to Richard, who was watching them speak to each other with a look of pleasant surprise on his face.
“Thank you, Jess. This was a very fine gift indeed, and I certainly appreciate the addition to my collection. It sounds like you have an excellent one of your own.”
“Well, hardcovers don’t travel as easily, Mr. Gilmore, and I travel light. One day I’d love to have a library as well stocked as yours, though.”
“Jess has mostly paperbacks,” Rory explained, “So he can carry them with him everywhere he goes.”
“I have seen you with a book or two in your handbag as well, young lady,” Richard observed. “Well, thank you both. I do think I’ll join you for dinner after all.”
Rory smiled and squeezed Jess’s hand, reassured that meeting her grandfather had gone just as well as she’d hoped. Rory had always known Richard and Jess would get along easily, much better than Emily ever would with him.
~
The dinner went much better than any of them expected, although Alessandra certainly wasn’t faring well by the end of the evening. Emily’s dagger-like insults aimed at Jess were often waylaid by Richard’s questions about his favorite books and authors, and Rory’s own discussion of her issues with coursework. Overall, it wasn’t as painful as it could have been, thanks to Richard’s presence at the table.
Sometime during dessert, Jess coughed and Rory smiled at him. She finished eating her poached pear quickly and regretfully announced, “Grandma, Grandpa, thank you so much for dinner. I really ought to be getting home.”
“Oh, yes of course, Rory. We’ll see you both at the funeral tomorrow,” Emily reminded them, as though Rory could have forgotten about it.
She nodded at Jess and stood up from the table, kissing Lorelai on the cheek and then going first to her grandmother, and then her grandfather to wish them a good night.
“It was very nice to meet you, Mr. Gilmore,” Jess added respectfully.
“Thank you again for the book, young man,” Richard replied, and Emily pursed her lips as she had done every time Richard showed a modicum of approval for Jess throughout the evening.
“And Mrs. Gilmore, thank you for the invitation to dinner tonight.”
“Yes, of course,” she responded shortly. “We’ll see you tomorrow. Drive safe,” she added to Jess with a glare in her eye. Thank goodness they hadn’t seen his car, or they probably wouldn’t let Rory into it with him.
They escaped quickly through the front door, retrieving their coast from the flustered maid, and drove off before anything else could be said or done.
It wasn’t until they were on the I-91 headed south towards New Haven that Rory and Jess breathed a sigh of relief. “That went well,” Rory said.
“It really did,” Jess admitted. “Although I didn’t have a black eye this time, so I guess I’m not surprised that it went marginally better.”
“Marginally?!” Rory asked, laughing. “I can’t believe how well it went. You’re in. Emily Gilmore may never approve of you, but my grandfather loves you.”
“Well I guess we’ve got to make this thing work, then, huh?” Jess asked, leaning over to kiss Rory as they stopped for an accident, the cars slowed to a halt in their lane.
“I guess so,” Rory agreed, shaking her head.
“You working tomorrow?” Rory asked.
“Nah, Luke gave me the day off so that I can come with you. So I’m all yours.”
“Oh goodie,” Rory said conspiratorially. “Then I guess I should mention that Paris texted to say she’ll be with Asher tonight?”
“Oh, really?” Jess asked, pretending not to understand the implication. “Well, I suppose I’ll have to stay the night and keep you company.”
“I suppose so,” Rory agreed flirtaciously, and reached over to hold his hand as the traffic lightened and they made their way back to Yale.