The ring felt like it was burning a hole in Jess’s pocket, and honestly, at any other moment, he would’ve been nervous about keeping it on his person, in the fear of accidental discovery. But the one person he was afraid of finding it was safely in New York for an interview, and wouldn’t be back until late that evening.
So that left Jess watching her daughter, someone he had thought of as ‘his’ for longer than he would admit out loud, and considering that she referred to him as “Dada” (and no, he didn’t cry when she first called him that, he just got a little teary eyed, thank you very much), she clearly didn’t mind. But Leia was napping and that left him with an even more terrifying prospect than proposing to the love of his life: talking to her mother.
As he slowly approached the couch in the living room of the home that Rory grown up, he had to take a few calming breaths. Lorelai was engrossed in the TV show she was watching, and didn’t even notice him until he was right next to her. She gave him a nod of acknowledgement, before returning to her show.
Sure, they had come a long way since they had met, and she had been more than cordial towards him for years, always fine with him taking up their couch when he visited, and as far as he knew, didn’t even voice any objections when Rory and he started dating again. However, standing in front of her now, he felt like he was seventeen again and not knowing how to talk to her. He knew he had to try though, and Luke was at the diner, so this may be his only opportunity to get to talk to her alone for a while.
“Lorelai,” he said, gaining her attention once more. “Do you have a moment?”
“I have many moments,” she said immediately. “Are you looking for a happy one? A sad moment? More serious?” He stared at her pointedly and she just grinned. “Have a seat, oh broody one. I thought we lost monosyllable man years ago. Nice to see him again.”
He shrugged and sat down on the chair. “I actually had something I wanted to ask you.”
“A full sentence! New Jess has returned,” Lorelai proclaimed gleefully, only pausing to switch off the TV. “What’s up?"
Not sure how to word it, he pulled the ring box out of his pocket and placed it on the table, flipping the cover open to reveal its contents. Of course he should’ve known better, because Lorelai’s eyes widened, immediately glinting with wicked glee, as she put her hand dramatically on her heart.
“Why, Jess, this is just inappropriate,” she began, and he was briefly confused, before she went on full speed ahead. “I’m a married woman, to your uncle no less, and you are dating my daughter! As irresistible as I am, I am not Stacy’s mom or Mrs. Robinson, so you will have to just accept the rejection for what it is. And your proposal skills need work.”
Jess barely refrained from groaning and just raised an eyebrow, causing Lorelai to pout at his lack of reaction.
“When you do that, you remind me way too much of Luke,” she pointed out. “It’s creepy.”
“Well, now you know how we feel with you and Rory,” Jess pointed out, causing her to chuckle.
Growing serious, she added, “It is a pretty ring.”
Jess nodded, picking it up and twirling it in his hand. The white gold ring had a modest diamond in the shape of a circle surrounded by tiny sapphires on each side. He hoped Rory would like it, as he had seen her admiring something similar just a few months prior. “So what do you think?”
“Going to have to use a few more words there,” Lorelai suggested.
“Of me proposing to Rory,” Jess asked. “I guess I’m asking for your permission.”
Lorelai nodded slowly. “I see, so you decided to throw a twist on the old patriarchal tradition of asking the father?”
“Yeah, well, I know the whole thing is outdated, but hey, I figured it’s also a way to give you a head’s up,” Jess explained.
“Why?” Lorelai wanted to know.
“Why what?” Jess asked.
“Why are you asking?” Lorelai clarified. “Rory and you are both adults, and if there wasn’t enough proof, there was a small child sleeping one room away as a reminder. So why do you need my permission?”
“Because it’s you,” Jess said, shifting. “And Rory will always care most about what you think. Plus, I know we don’t have the greatest history. I … well, I wasn’t always the easiest to get along with, and you haven’t said anything about Rory and me now, but-”
“You were also a teenager,” Lorelai interrupted. “I could’ve cut you a little slack.”
“I could’ve been less of a jerk and earned it,” Jess offered.
“You just reminded me so much of …” She trailed off and Jess was a little worried where she was going to go with it.
“Of Rory’s dad?” he asked, trying not to wince.
“Of me actually,” she admitted, letting out a weak laugh, surprising Jess into silence. “You had this ‘do what you want’ attitude, and refused to fit in, even when it would’ve been easier. Except it wasn’t Hartford society, and I guess I believed if you didn’t love Stars Hollow, there was something wrong with you.”
“It certainly is a place that grows on you,” Jess acknowledged.
“And if I hadn’t gotten pregnant with Rory, who knows how I would’ve turned out?” Lorelai said.
“Rory was lucky to have you,” Jess said frankly.
A look of sympathy crossed her features. “Yeah, I was lucky to have her. And that is probably another reason I could’ve been easier you on you.”
“Luke told you stuff?” Jess asked, unable to hide his reaction this time. He didn’t want anyone’s pity.
“Hinted over the years,” Lorelai answered. “And well, I do know Liz.”
“She’s better now,” Jess sighed. He had been worried for years, especially about Doula, but it seemed that as weird as TJ was, he was a good guy, and she had actually settled down in to whatever her version of normal was. And it hurt at first, but most of what he felt these days was relief.
“Yes, she is,” Lorelai agreed. “And you grew up. I have to admit, when Rory told me that you suggested that book to her, I wasn’t thrilled about you two interacting.”
“Oh.” That stung a little, especially since it wasn’t that long ago, and he thought she had been okay with him by that point.
“But,” she said hurriedly. “Clearly, you knew what she needed, and with the way you’ve stayed and how you are with Leia, it’s hard for me to say that you’re not exactly what she needs. And clearly what she wants. So if you need my permission, you have it.”
“Really?” Jess hadn’t known what to expect, but it seemed as if it shouldn’t have been that easy. “I do love her, both of them, and I promise I will always be there for them, and never leave.”
“Jess, I saw you spend thirty minutes putting Leia’s hair into buns so she could be Princess Leia for Halloween,” Lorelai reminded him, her expression amused. “You don’t have to prove anything to me. I can see it.”
He nodded, grateful. “Thank you, Lorelai.”
“Thank you, Jess,” Lorelai countered. “You make Rory very happy, and even Luke is thrilled that you’re around so much. Though seriously, more words when you actually propose okay? You can’t just shove the ring at her.”
And all Jess could do was laugh in response.
In comparison, telling Luke was fairly easy. He was helping him clean up the diner and just brought it up casually, as he wiped down a counter.
“So I’m going to propose to Rory,” he remarked casually, causing Luke to freeze.
“Really?” Luke asked.
“Yeah,” Jess confirmed.
“Huh,” was the response he got.
“Yeah,” Jess repeated. “So what do you think?”
A shrug and Luke told him, “Well, you’re not a prince in line for the throne, but I guess you’ll do.”
“What?” Had his uncle lost his mind?
“Never mind,” Luke said, waving a hand. “You happy?”
Jess nodded. “Very.”
“She seems happy too,” Luke remarked, words that warmed Jess to the core. That sort of affirmation from one of the people who loved Rory the most, especially since it was the person he admired the most, was special. “Good for you two.”
“Well, as long as she says yes,” Jess said, only half joking.
“She’ll say yes,” Luke said confidently.
“Thanks, Luke,” Jess replied.
“Any time, Jess,” Luke told him, as they exchanged smiles and got back to work.
And it was just that easy, as it had been for years with Luke.
With both the blessings that he needed, he only needed to get the one yes that mattered most. So on a bright sunny weekend morning, once Lorelai and Luke agreed to watch Leia, Jess packed a picnic basket full of Rory’s favorite foods and convinced her to go out with him for the afternoon. As much as he would’ve loved to bring Leia along, he didn’t want to bring in added pressure in the case that Rory did decide she wasn’t ready/didn’t want to get married after all.
“So where are we heading?” Rory asked, as they took a walk toward Jess’s chosen destination.
“That would be a surprise,” Jess told her, carrying the picnic basket in one hand, the other entwined with Rory’s. “So you’re just going to have to be patient.”
“There’s food involved,” Rory pouted. “How can I be patient?” She nudged him playfully. “Speaking of which, do I have to bid on that basket?”
“I will let you off the hook this time,” Jess teased. “But I have to say that my food would be much more valuable and edible than whatever I paid for that nonsense you tricked me into eating.”
“Clearly the payment was for the pleasure of my company so the food is irrelevant,” Rory retorted.
“Well, in that case, I clearly didn’t pay enough,” Jess said, grinning.
Her smile widened. “You’re such a sap.”
“Don’t spread it around,” Jess warned. “I have a reputation to maintain.”
“Oh, please, whatever reputation you think you had, you lost ages ago,” Rory scoffed. “Basically everyone in this town has seen you push Leia around in her stroller so you can say goodbye to that bad boy image. Unless it’s Taylor, I guess, who is probably the only one that doesn’t seem to believe that you are no longer seventeen and stealing garden gnomes.”
“Well as long as Taylor doesn’t like me, I’m still doing something right,” Jess remarked, with an easy smirk.
Rory was about to comment, but then she realized that they had arrived at their destination, and her eyes lit up. Much like the rest of town, the pier overlooking the lake was exactly the same as it had been all those years ago.
“Keeping with the theme, are we?” she asked, visibly pleased.
“Yeah, I figured why break tradition now,” Jess offered, placing the picnic basket in the middle. Pulling out a checkered blanket, he set up their picnic and gestured for her to take a seat, which she did, and he took the one opposite of her.
“This looks great,” Rory said admiringly. “I think if your basket was up for bidding, I would have some stiff competition.”
“Clearly my basket is for your eyes only,” Jess told her.
“Dirty,” she teased.
“Oh geez, now you sound like Lorelai,” Jess snarked.
“And you just sounded like Luke,” Rory shot back, causing him to chuckle and shake his head.
“Now that’s terrifying,” Jess said. “I didn’t think the becoming like your parent/parent figure thing happened this early.”
“Well, once you have kids, you are officially in danger,” Rory pointed out. “Though really, the food looks great. You could’ve made a killing a week from now.” Her eyes narrowed. “Wait, was it a coincidence that you chose this date or-?”
“Or?” Jess urged.
“Did the bid a basket happened today all those years ago?” Rory asked, amazed. “No way.”
“Like I said, why break tradition now?” Jess offered. He had a vague idea about the exact date, but one in depth search into the Stars Hollow Gazette archives gave him the answer he was looking for.
“Jess.” Rory softened. “Why?”
“Because,” he explained, “It was one of the first moments.”
“First moments?” she repeated.
“Yeah, that I realized that this, that you were more than just the only person I could stand in town, more than just a girl I had a crush on,” Jess confessed. “Just … more. I don’t know if it was love yet, but it was something more than I had ever felt with anyone else before.”
“Jess,” she tried again.
“And I know I was kind of an ass, and you had someone,” Jess said. “But I couldn’t help it. You were the only one that saw me.”
“Well, it’s not like I did much protesting,” Rory reminded him. “I liked being around you. I always felt most like myself with you. I still do.”
“I think that goes both ways,” Jess said, heart skipping a beat, as she closed the distance between them and kissed him. That part never got old.
“So now we can eat?” she asked, once they had parted.
“I know better than to keep a Gilmore away from food,” he said, mock seriously, as he unpacked the plates and food, dividing it easily.
“Always knew you were a smart man, Jess Mariano,” she proclaimed, as they delved into their food. “And a good cook. I am definitely keeping you around.”
“Well, I don’t have any plans to go anywhere,” Jess promised her, bringing another smile to her face.
“Good,” she said, a touch of smugness in her tone.
As they continued to eat, they made light conversation, Rory eagerly bringing up a new band she had learned about via Lane and Jess was able to tell her about the latest book he had been reading the night before. Squeezing in date nights with a kid around and both of them pursuing their careers was hard, so it was a pleasant change. The ring in his pocket was always at the back of his mind, but he was trying to do his best to enjoy the moment.
As silence fell between them, Rory glanced around sand said, “Man, this place really feels the same. Though I have to say, I’m glad the evil swan is long gone. Mom says she hasn’t seen it in years.”
“Evil swan?” he echoed, trying not to cringe.
“Yeah, we even had a name for it,” she said thoughtfully. She must’ve seen something in his face, because her eyes immediately widened. “Did you see it too?”
“I don’t know if I saw the one you’re talking about,” he admitted, “But I certainly met an evil swan. Do you remember my black eye-?”
“Yes,” she said, recognition dawning on her face. “Are you telling me?”
“I got beaked,” Jess said, old humiliation over the incident coming up to the surface.
“No way!” she exclaimed. “Jess, why didn’t you tell me?”
“I was embarrassed,” Jess told her. “I only told Luke.”
“Aww, Jess,” she said, eyes shining with mirth.
“It’s okay, you can laugh,” Jess assured her. “I know it’s ridiculous.”
“I wish you had told me,” she replied, a small giggle escaping.
“Yeah, well, I could’ve said a lot of things I didn’t,” Jess said, as they continued to eat. “Words weren’t always my thing. Probably isn’t completely now.”
“Hey, no self-hating,” she said, poking at his chest. “I didn’t say that to make you feel bad. I was just making a comment.”
“I know you weren’t,” Jess said. “I can’t help it sometimes.”
“We both made mistakes, but we’re here now, and that’s all that matters,” Rory stated firmly. “So deal with it.”
“Worse things in life to have deal with,” Jess insisted. “I love you.”
Her whole demeanor seemed to brighten. “I love you too.”
He would never get tired of hearing it, of saying it. And he couldn’t imagine ever not feeling it. That’s when he knew. He had been trying to figure out the right moment, but he couldn’t imagine a more right one than the one they were sharing.
“Especially,” Rory added, peaking into the basket, “Since you seem to have brought pie. Is that chocolate cream? Because you are outdoing yourself-”
“Marry me,” he blurted out.
“What?” she asked, mouth dropping, hands falling to her side.
In a swift motion, he took her hands, and pulled them both to their feet. She allowed him to guide her a few steps away, and he fell to one knee in front of her. Her blue eyes were watching him in awe. So Jess took a deep breath, one hand going into his pocket of his jeans, to reconfirm the ring was there. Pulling it out, he opened the box and took out the ring, offering it to her. Her eyes didn’t leave his face.
“Marry me,” he repeated. “I love you, I’ve always loved you. I am not sure if I ever really stopped and I don’t think I would ever want to now. You’re the best thing that’s ever happened to me and from the moment I saw you, I knew we were meant to be together. There’s nothing more I want to do than make you happy for the rest of our lives. Will you marry me?”
“Yes!” Rory exclaimed, grinning. He had noticed Rory had already nodding halfway through his speech, but he wanted to say what was in his heart.
“You want to think it over a moment?” Jess teased.
“Hand over that ring, Mariano,” Rory demanded, mock glaring. Jess slid it onto the ring finger of her left hand, before standing up once more.
“Not even married yet, and already bossing me around,” he joked, wrapping his arms around he waist.
“Yeah, well, no take backs now,” she warned, her arms settling around the back of his neck. “There may have been no vows yet, but there’s only one way you’re getting out of this.”
“Somehow I’ll survive,” he drawled, as their lips met in a kiss. She said yes. Somehow, that part hadn’t really settled in his brain until that moment. And he couldn’t stop smiling.
“Keeping me happy for the rest of our lives,” Rory murmured, one they separated. “Pretty big promise there.”
“One I plan to keep,” Jess said seriously.
“Does that include endless supplies of coffee and pie?” Rory suggested.
“Even that,” Jess agreed. “Luke may have a few objections, but we’ll figure it out.”
“I’m going to hold you to that,” Rory made sure to say.
“I’ll put it my vows,” Jess promised, leaning forward once more.
“Deal,” she agreed, as they kissed again.
And it was a promise that he intended to keep. Now and always.