Days later, Jess doesn't regret basically agreeing to be Rory's…boyfriend…but he sure regrets even mentioning it to Matt and Chris.

They interrogated him one day when the three of them were getting lunch on Monday. Rory was doing some work on her article for the zine and waved the three of them off saying they needed guys time and she needed to actually concentrate. Once they settled down they teased him mercilessly, noting that something had changed between the two of them over the weekend.

"Isn't this around the time you start getting bored and find reasons to nitpick the girl you're dating?" Chris asked. "I'm surprised Rory has lasted this long."

"Yeah don't fuck this one up, she's actually lightening up my load on the zine," Matt added.

Jess rolled his eyes. "Who says I get bored after like a month?"

"We do," his friends replied simultaneously.

"It's all fun and games but then it comes time for some actual commitment and you can't hack," Chris explained. "So is this the same thing once Rory leaves and goes back to school?"

Jess gritted his teeth in annoyance, mostly because they were right and that was his MO. "No."

"No?" Matt questioned. "As in no this isn't the same thing?"

"Why isn't it the same thing?" Chris added.

"Because…I basically told her I didn't want it to be over once she leaves," Jess groans.

The boys eyes widen and they let out a happy woop, shaking Jess's shoulders.

"Is she your girlfriend?" Matt teases.

"Can we not guys? Let's just eat. All I know is she's great, I'm great, it's great being together and I'm glad it's a thing. Can that just be it for now?" he tells them firmly.

The boys sheepishly nod and start to eat their sandwiches. They eat in silence for a few minutes before Chris quietly breaks the hush over them.

"She's definitely your girlfriend."

Ama is just as bad.

Jess finds it hard to meet new people, so when Rory introduced him to Ama during First Friday and left them to their own devices while she went and interviewed the artist she needed to for Matt, he was worried his introverted tendencies would fuck him over and make this new important friend of Rory's think he was a creep. Thankfully Ama seemed to get his dislike for small talk and noted how dumb it was as well.

"We don't need to do the small talk thing, I don't really need to know where you're from and your sad family history because I can tell doing all that will make you bolt so how about we sit in that corner and pick out the worst piece of art and see if there's any guys around here worth it for me to take home tonight?"

He simply nodded with a smile and followed her to an empty bench, both holding a glass of cheap wine they proclaimed was unnecessary if it was going to be so tart and managed to single out a bearded red head man that Ama deemed good enough for the task of ending her sex drought. He was surprised to see at some point during the night the way her eyes glazed over when she stared at a short brunette with long blonde hair, a curvy body and a nose ring. It was the kind of girl he probably would have went for if he didn't have Rory with him. When he and Rory walked over to the gallery and she talked up Ama and joked about her quest to end her horniness, she'd only mentioned Ama's specific types for a man. She'd never said anything about women.

He didn't say anything but merely observed from the corner of his eye the way Ama's eyes followed the girl for a minute, biting her lip. But then the red head man she ended the night with walked in and diverted her attention for the rest of their time. He played wing man for her and actually kind of enjoyed it. She was everything Rory said she was-blunt but with a politeness so that you could never say she was being a bitch. She seemed to like Rory, noting that they hadn't been friends long but that the girl had an innocence and wit that seemed mismatched but fun to figure out.

He and Rory had lunch with her on Thursday, getting a quick break from the craziness at Truncheon. He'd suggested a meal at Monk's since he was strangely craving mussels and Ama exclaimed to Rory that she'd found a good man with good taste. The three sat and Jess listened in and out of a conversation the girls had about Ama's 2nd date with Jerry the guy she met on Friday.

"He told me I'm the first black girl he's slept with and thought it was some prize of a compliment, I wanted to smack him," she told them rolling her eyes.

Rory's eyebrows furrowed in confused thought. "Why would he tell you that?"

"He probably thought it would make me feel special, that he grew up in the white suburbs, came to the city and is now open to the world of dating black women. I mean that's cool but I don't need to know all that."

"So what'd you say to him?" Jess asked with a smirk, already guessing she let him have it.

"I told him if he kept thinking he'd get a prize for it I'll probably be the last black girl he ends up dating." Ama tells them with the wave of a hand. "He's dismissed I don't have time for that."

Jess laughed while Rory frowned, obviously bothered by the interaction. Jess looks and sees her expression. "What's up Rory?"

"It just sucks he made you feel that way, he should just like you for you," she says sadly.

Both Jess and Ama smile softly at Rory, already experienced with the ways Ama's features set her apart in the minds of some people. Jess saw it all the time growing up in New York in Latino and black neighborhoods. Rory lived in a bubble for all her life and that was hard to remember sometimes. She still seemed to have this innate belief in goodness.

"It's ok Rory. I mean it's annoying but it's ok. He should just like me for me and not think of me or himself as a special snowflake given the circumstances but there's more where that came from," Ama explains indifferently. "Plus he was a pretty selfish lover, I don't know why I even went on that second date. Free food?"

Jess laughed and Rory was able to muster up a smile, eating her fries daintily. The three continued on with their meal until Rory's phone rang. She reached in pocket and her eyes widened at the name on her caller ID.

"It's my mom," Rory mumbled. She continued to stare at the phone, not knowing whether to answer it or not.

"You should take it, she's actually calling you for once," Jess whispers. Rory nods and excuses herself from the table, hurrying outside to take the call. He and Ama watch her go, similarly hoping this call did not end in frustration and tears.

"Her mom usually doesn't call her, Rory has to make contact these days," Jess notes. "She calls her like once a week maybe? But the conversations never last more than five minutes because they're full of the general check up niceties. She cried the first time."

Ama gives him a sad smile and takes a sip of her beer. "She told me a little bit about it, it sucks."

"It does. They're close."

"I told her it's not surprising. That in the end her mom is her mom and no matter how cool she is she thinks her daughter's life should be a certain way. And I guess shacking up with a 23 year old guy in a strange city isn't part of that."

"I wouldn't think so," Jess agrees.

"Good," Ama says putting her beer down. "So I hope what's happening here is worth all of that grief," she tells him with a serious face.

Jess pauses, scrutinizing Ama for a moment. He didn't think her blunt nature would be turned onto him. "Excuse me?"

"I like you Jess, you're very much living up to the hype of Rory's words. She seems very happy with you. But I hope you remember this isn't her real life, here in Philadelphia. That she has a whole world that includes a mother she considers to be her best friend. And she should make whatever choices she wants to make, I really believe that, but I hope that whenever she leaves here, whether it's tomorrow or the day she has to go back to Yale that she doesn't leave here thinking you wasted her time."

Jess swallowed hard, shrinking under the hard gaze of this girl. "Did she tell you about Friday morning?"

Ama shook her head in denial.

"I told her that I couldn't see this ending when she leaves. Look I have a hard time with relationships, it's probably because my mom fucked me up with her flakiness and bad string of boyfriends when I grew up. I had one girlfriend in high school but she was more like my best friend I would sometimes fuck. I don't know what a good relationship looks like."

"Well I hope you can figure that out because Rory doesn't seem like a fling kind of girl to me. She seems like a relationship girl. I haven't known her very long at all, but she is so determined to be as good for you as she thinks you are for her. That's not a girl that let's things go after a couple months," Ama observes.

"You're right. You are. And I knew that going in but I still did it. I still told her to come here, I didn't tell her to leave when she did, and now here I am wanting to try to be what she needs."

Ama nods. "Good. Well your trying may have to start again soon if that conversation outside doesn't go well. Step one in being a supportive boyfriend."

Jess grimaces. "Don't say boyfriend."

"Boyfriend," Ama challenges. "It's what you're working towards. Say it with me…boyfriend."

He frowns and eats some fries in protest. Ama chuckles and takes a long draw of her beer. "She'll get you there," she promises.

After what seems like forever Rory walks through the front door with a sheen of sweat on her face from the humid, hot weather. She has a worried look and once she locks eyes with Jess she bites her lip in nervousness and returns to the table slowly.

"I have to bail on our trip to the arboretum on Saturday Ama, I'm sorry," Rory says sadly.

"Oh…it's ok. We've got time I guess. Why what's up?"

"I…I need to go home. I need to go back to Stars Hollow."

When Rory gets outside and answers the phone she's not sure what to expect from her mom. Their short phone calls during her time in Philadelphia had been painful, not because her mother was harsh or mean with her words but because of how short and plain they were. Rory would call, wanting to bridge the gap and find some way to make Lorelai understand where she was coming from, but all she got was a brick wall. They would exchange hellos, Lorelai would ask if she was ok, if she had enough money, and if she was coming home yet. Rory would reply, yes, yes, and no she wasn't coming home yet. She wasn't ready. Lorelai would stew in silence, Rory would ask after Lane and meekly ask how things with Luke were going. That always felt touchy, a subject that would bring rapturous stories if things were normal between them but all Rory got was a simple good.

Rory cried after the first time but she refused to the next. Jess looked almost guilty when she cried, knowing that he was a catalyst to all of this but in the end these had been Rory's choices and he had in no hand in them. He didn't make her do anything and he certainly didn't make her mother take a turn and become more like Emily in the way of holding her daughter to an unachievable expectation of morality.

Lorelai hadn't called her before though, so maybe this was a turn.

"Mom?" she answered earnestly. She waited a beat for a voice to take over.

"Hey kid," her mom answered. Her voice was scratchy and Rory recognized right away it was the way her voice turned when she'd been crying.

"I…were you crying mom?" she asks concerned. "What's wrong? Is everything ok? Are grandma and grandpa ok?"

"Everyone is fine," Lorelai assures her. "Mom is still away and dad is living like a bachelor. So weird."

Rory laughs at the thought. "I can't imagine that, I bet he's still afraid to go in the main house thinking grandma will catch him all the way from Europe."

"Oh you know it," Lorelai agrees. "The Gestapo have eyes everywhere!"

"Mom!" Rory chastises. This felt all too familiar.

"Sorry, sorry no more Hitler jokes." Lorelai promised.

Rory giggled and a silence passed between them.

"How are you Rory? Are you safe? Do you need money?" Here it was.

"I'm good…I'm really good mom. I'm safe. I don't need money," she answers mechanically.

"Good…good."

"How is the inn?"

"Good."

"How is Lane?"

"Good."

Rory grows frustrated at this point, sick of having this same conversation over and over when she knows what's going to be said. "Mom why did you call?"

"Excuse me?"

"We do this every time, you don't want to actually talk to me until you hear me say I'm coming home. But I'm not coming home right now, I'm not ready."

Her mom lets out a big sigh. "And why aren't you coming home huh? Jess hasn't gotten sick of you? What are you going to do if this fling you're having blows up in your face tomorrow? What are you doing Rory?"

"I'm with him mom! I don't understand why I have to keep explaining this to you?"

"You didn't even know anything about him Rory except that he wrote a book when you ran away to him Rory."

Rory clenched her eyes and let out a hard breath. "That's not fair. I know a lot about him now."

"Oh really," Lorelai mocks. It's almost like a challenge.

"Yeah, I do. I know that his birthday is Christmas Eve and that his mother was so hopped up on drugs that she intended to name him Jesus but forgot the U. I know that he didn't graduate high school because he thought it was more important to find his father who abandoned him as a baby so that he could finally figure his life out. I know that he likes vanilla coffee, he doesn't burn in the sun easily, and when he drinks whiskey he's more likely to reference Notorious B.I.G. lyrics. He writes best when he's by the water even though he hated California so he rented a shore house for us in a couple weeks so that he could finally break his writer's block. And most of all I know that when I do leave here this will not be a fling because he told me it wouldn't be. That I shouldn't be with anyone else because he doesn't want me to leave."

She was breathless and holding back tears, so angry that she had to defend herself and defend Jess against someone she always believed was so…cool. It was surprising to her that for all her mother's missteps, she'd forgotten them so quickly and turned it around to judge Rory harshly.

"He wants to be with you?" Lorelai asks weakly.

"He does," Rory confirms.

Silence takes over again.

"You're going to burn like hell on the beach," Lorelai finally says.

Rory rolls her eyes. "Seriously?"

"It's true!"

Rory smiles to herself, leaning against the building for support and looking out into the crowd of people walking up and down the street.

"I just miss you kid. You've been so off lately, especially before you left. You have to understand that what I was seeing, it wasn't the kid I raised. I didn't raise you to be that irresponsible, I didn't raise you to be…the other woman in someone else's marriage. You know Dean is still with Lindsay?"

"I don't want to talk about Dean mom," Rory hisses.

"Well we have to at some point. You had sex with a guy you don't know, kissed your married ex-boyfriend, and then ran away to live with your one night stand you knew nothing about for the summer. It's just not what I wanted for you."

"And you're entitled to that because you're my mom, but you're also supposed to be my best friend. Isn't that what you tell me all the time?"

"Well I pulled the mom card."

"You can't do that! You can't just play that card when it becomes convenient!"

"That's not what I'm doing!"

"Yes you are," Rory says firmly. "You're playing your mom card to judge me right now when a best friend wouldn't do that. Mom I'm an adult now and I have to make my own decisions. When I was younger you could do this and I had to go with it because you had the pop tarts and the money for the coffee but it's not like that anymore. You can't do this."

Her words get caught in her throat by the end and she feels a cry coming on. She swallows hard and tries to continue.

"It really hurt when you tried to dismiss me to Europe like I was some shameful person you had to hide away. It was so…it was really Emily of you. And I didn't expect that. I probably would have gone with grandma on my own with my own convincing but once you did that I couldn't do it. So I came here. And I've been really happy here mom. Jess is so great, and you'd like him actually. I made this great new friend and I swear you'd want to shop in her closet. I'm working with one of the guys at Jess's publishing house and interning with him on the zine they do. I went to this art gallery Friday night to interview an artist and it was so weird but it was fun to write about because it was different. I eat Philly cheesesteaks all the time even though Jess hates going and I'm working through a list of all the coffee shops to declare which place is the best by the end of the summer."

Lorelai continued to not say anything but Rory could hear her crying and her heart sank. She hated that.

"For what it's worth I miss you too. I miss you so much," she whispered.

Lorelai continued to cry, "I was like Emily? God, Rory how could you…I was like Emily?"

Rory rolled her eyes. "That's all you got about that?"

"What kind of mother am I?" Lorelai cries.

"The kind that had a daughter who didn't rebel for 19 years?" Rory questioned.

Lorelai laughed through her tears. "You really know how to work through a phase kid I'll give you that."

"I am a perfectionist. Can't stop until it's right."

Her mom sniffled. "I'm really sorry you felt that way kid. I just wanted to protect you."

"I know you did mom…I know."

The short walk back to Truncheon is quiet. Rory walks behind Jess with her head down, unable to look at his body fraught with tension and stalking down the street. She walks fast to keep up with him but she's just barely able to do it. She realizes now that she didn't explain herself or her impending departure very well. And she probably shouldn't have just done it with Ama as an audience. Both of them had looked at her surprised, but once the words settled in, Jess's jaw clenched and he mumbled that he had to go to the bathroom and that they should be getting back. He dropped some money on the table and basically did god knows what in the bathroom until they were ready to go. Rory informed Ama more about what was causing her to leave and they said their goodbyes with the possibility to have a quick coffee and chat before she left the next afternoon.

She paid for their lunch and once Jess came out of the bathroom he led them out without a word.

When they arrived back to Truncheon he picked up his notebook and told Matt and Chris he was taking the rest of the day off to write by the river. It had been working for him lately but not enough to totally push through some of the blocks he was experiencing with his writing.

He ignored Rory as he walked out the door and she blinked back tears, not used to this cold, angry side of Jess. She imagined that when he got mad it would be visceral and harsh but not this. Rory looked to Matt and Chris and told them she would be back in a few minutes. She knew she had to finish the layout of the zine for the printers tomorrow but this was important.

She ran outside and saw Jess already down the street, still walking fast. She had no choice but to run after him, glad she wore her keds today instead of the cute sandals. It never seemed like she was getting near enough to him so she shouted out to make him possibly slow down.

"Jess, wait!" she yelled.

He stopped but didn't turn around, walking to the side to move out of the way for passersby going at his pace. He turned towards her, arms crossed and waited until she came to a slow stop from her jog, panting and holding her hip.

"I didn't know you could walk that fast," she said breathlessly. He didn't respond, looking past her. They stood for a few minutes while Rory caught her breath.

"Shouldn't you be packing?" Jess finally mumbled. "It's not like you brought much but I'm sure you'll want to hightail it out of here soon."

"Jess, no it's not what you think! I'm not going back, going back. I just need to go for a few days, a week at the most."

"Oh," his hard exterior softened at the revelation.

"Yeah. I should have phrased it better earlier."

"Well I jumped to a conclusion."

"You did."

The two fell back into silence and Rory wiped the sheen of sweat on her face.

"When are you leaving?" he asked.

"Tomorrow afternoon. My mom wants me to come to Friday night dinner with my grandpa."

"So you two are ok?"

"We're getting there, that's why I'm going home. We hashed out a lot of things over the phone earlier but it's not the same. I think if I wait this out totally all summer it'll make things worse once I go back. And even though I was so mad and hurt by her, enough to run away, she's still my mom. She's really important to me. So I have to go back just to make sure things will be ok for her and me because I would hate for it not to be. Can you understand that?"

At a certain point, he couldn't because this was not at all the relationship he shared with Liz. But he could understand that Rory didn't feel whole right now and that was largely because she didn't have her mother to share in any of her joys with. She had told him this quietly in bed yesterday morning when he'd asked her how much she missed her mom. She broke down and he held her as she talked about how happy she was here but how lonely it was for her best friend to not see that.

So he didn't understand it for himself, but he understood Rory needed this.

"I do," he tells her, taking a step towards her. She takes a step towards him and reaches for his hand.

"I promise I'm coming back. I'll even leave something you know I can't live without for more than a week so that you see," she promises.

"You don't have to do that Rory. If you say you're coming, I have to trust you're telling the truth. And that's what this whole relationship thing is about right?"

"Yeah…yeah it is. And I will call you because I'll miss you."

"Yeah I was getting used to you kicking me at night," he smirks.

She scoffs and shakes her head. "I do not do that!"

"Yes you do and I get a glorious week break from it," he mocks.

"Whatever, you know what else you're getting a break from," she challenges.

He thinks that over for a second and frowns. "Whatever I'll just call you."

"Ew, I'm not doing that!" Rory throws her hand up in disgust.

"Don't knock it till you try it."

"I'm not having phone sex with you in my childhood bedroom," she opposes.

"Whatever you say, you'll have a drought too."

He's smiling now, his face brighter than when he left Truncheon and Rory feels relieved.

"Were you that hurt Jess…that I was leaving?"

Jess blushes and looks down. "I mean…we just kind of figured out what was happening with us and then you just leave…"

She pulls him closer and leans up to kiss his cheek. "I swear I'm coming back. You're going to go to the river and do some writing, I'm going to finish putting together the zine and when we're both done I want a banh mi sandwich for dinner and you get to pick a movie."

He fights the grin on his face. "Even if I pick Almost Famous even though you keep saying you hate Kate Hudson?"

She resists the urge to protest and takes a deep breath. "Even if you pick Almost Famous."

He nods and kisses her cheek and then her lips quickly. He reluctantly lets go of her hand and waves as he walks off into the crowd. Rory watches him go until she couldn't see him anymore before turning around and slowly making her way back to Truncheon.

This was the right thing to do, she thought to herself. The best way to restore some kind of order to all the parts of her life.

She was happy with Jess, but what would that mean if she and her mom weren't ok?