Lorelai, Rory, and Anna were at Doose's looking for a basket for the annual Bid on a Basket Fundraiser that the town held. "So, I've decided I'm saving myself for William Holden," Lorelai told her daughters.

"Wow, it's nice out here in left field." Rory lifted an eyebrow.

"And a very odd choice." Anna was looking at more pricey baskets. She had saved up her tips from Lukes to get a basket that she can use all year round. And, that way she wouldn't have to buy a basket every year that would only get thrown away by the end of the day.

"Hey, I'm sorry. Sunset Boulevard was on last night, and I don't know…I've known him for years, Sabrina, Stalag 17, and yet last night something snapped." Something in her said this was the man for her.

"I'll say." Rory laughs.

"I think it was the monkey scene." She told them, getting a look from her daughters.

"You know he's dead, don't you?" Rory informs her.

"The monkey?" Lorelai asks.

"William Holden!" She yelled.

"The movie was made in the 1950s, so it's safe to say the monkeys are dead too." Anna looked at the picnic basket set that came with a blanket, a thermos, plates, containers, and utilities that match the blue fabric lining in the basket. It was around 200 dollars but with all the stuff in it, she felt like it was worth the money.

"Ugh, every great relationship has its obstacles. You'd know that if you weren't dating Andy Hardy." Lorelai playful scoffs.

"This one?" Rory held up a big basket.

"Hm, no." She shook her head.

"Why?" She asks.

"It's too big, it raises expectations." She explained.

"Like there's a home-cooked lunch in there?" Rory smiled.

"Instead of whatever is leftover in our refrigerator... exactly." Lorelai nods.

"Okay, going back to the pile." Rory put the basket back

"I'm getting this one." Anna picked up the suitcase-style picnic basket.

"You sure you want to spend all that money?" Lorelai asked. Anna nodded her head. "Alright, you let Taylor know it's the food in it he's selling, nothing else. If the guy gives you a problem let me know."

"Which guy, the one that buys it or Taylor?" Anna asks.

"Either, I'll kick whos ever ass for my kids." Lorelai puffs her chest out, before deflating as she goes back to looking at the baskets. "Oh, it's quaint, isn't it? The women get to make a nice lunch basket, the men get to bid on it, and the world rotates backward on its axis."

"I think it's fun." Rory smiled.

"That's because you have a pretty boy to bid on your basket." Lorelai smiled.

"Yes, I do." She nods.

"I'm going to go look for ingredients." Anna put her basket into her cart and went down an aisle. She was putting a bag of flour in her cart when her sides were squeezed making her jump and scream. "Jess, what the hell?" She punched his arm.

"Oh my god, is that a basket? You're going to that thing." He looked into her cart.

"Yeah, it's tradition. I've been doing this since I was eleven when we first moved into the house." Even though she lived in Stars Hollow her whole life they didn't start participating in town events until they moved out of the Inn. Before that, they were kept busy with Inn events that they didn't have time for town ones.

"Who was buying an eleven-year-old's basket? That's just creepy." He cringes at the thought of a child having a picnic with some strange man.

"Rory and I thought it was romantic. We begged my mom to let us join in. So, she got Michel to buy our baskets, the year after that was Morey, and then Jackson." She pushed her cart to the produce section to put lettuce and tomatoes in.

"So, who is buying it this year?" He asked.

"Thomas, I told him I would pay him back later and make his favorite dessert." She grabs some lemons.

"So, it's a date?" He asks.

"No, we are going to meet our friends and have a big picnic." She explained.

"Sounds like a fun day." He hummed.

"I hope so." She smiled.

On the day of the fundraiser, Lorelai, Anna, and Rory were walking down the street with their baskets. "You know what's wonderful about this festival?" Lorelai asks.

"No, what?" Rory asks.

"That always falls on the day after trash day. Therefore, all the stuff that you forgot to throw out that you would normally be stuck with for another whole week, you can instead put in a pretty basket and auction off for charity." She held up her basket.

"That is less wasteful." Anna nods.

Lane runs up behind them. "Okay, I've got it all worked out."

They turn around to address her. "Tell please."

"Well, I invited my cousin David to come and bid on my basket, you know, to keep my mother happy." She adds what she needs her cousin for. They nodded their heads. "Then when he gets it, we tell my mom we're gonna go eat over to the park where Henry's gonna call on the payphone at exactly two o'clock for the 'all is clear' sign. Then David, with the twenty bucks I give him, will disappear, Henry will arrive, and we'll finally have our first official date."

"All those times I sat at Luke's counter wasn't a date?" Anna put her hands on her hips.

"It will be the first date we can be alone." She clarified.

"My head is spinning." Lorelai never knew of someone with such a complicated dating life.

"Stash this at Miss Patty's for me, okay?" She held the basket out to Rory.

"Don't you need this for David to bid on?" She took the basket.

"Oh no, my mom packs that one. You know, homemade granola, wheatgrass juice, soy chicken taco." She made a face as she described the healthy food.

"Suddenly our lunches are looking pretty good," Lorelia said to Rory, who nodded.

"I don't know. At least Mrs. Kim's doesn't have the chance of being spoiled." Anna saw them putting food in their baskets that they had in their fridge for months.

"This is the Henry basket. I went by Gianelli's and picked up a couple of meatball heroes and some chips. I also packed a change of clothes, makeup, makeup remover, and three temporary tattoos." She listed off on her fingers.

"Sure, 'cause four would be trashy." Lorelai teased.

"I gotta go. I gotta sneak back into my house. Oh, I'm so excited!" She runs off.

"Ah, man. I remember the days of lying to my mother about a boy. Once I had a boy hidden in the closet and of course, Mom wouldn't leave, so I finally had to pretend to get sick to my stomach just to get her out of the room long enough for him to climb out the window and down the tree. He fell, broke his leg. Ah, to be young again." As Lorelai told the story, her daughter's face went from smiling to concern frowns.

A crowd that was divided with women on one side and men on the other were gathered in front of the gazebo filled with baskets. Taylor stands at a podium in front as the auctioneer. "Sold for fifteen dollars to the man in the yellow. Thank you very much." A pink basket was given to a man in a yellow jacket. "Now the next basket I have here is a lovely green wicker number that would be a charming addition to any room once the lunch is gone. Let's start the bidding at five dollars. Do I hear five?" Taylor picked up Lane's basket.

"Five dollars." David raised his hand after getting the nod from his Auntie.

"Okay, I have five dollars. Do I hear ten?" He asked the crowd.

"Ten dollars." Kirk raised his hand. Mrs. Kim glares at him. "Withdrawn." He put his hand down.

"Okay, I'm still at five, do I hear ten?" Taylor asked. Mrs. Kim glares at the crowd of males making them look at their feet. "Five going once, five going twice, sold to the young man for five dollars." David went up to the podium with Lane running after him. "You know what's nice, you can put a couple of extra rolls of toilet paper in there and stick it someplace in the bathroom, decorative and convenient. Now this next one…" Taylor advised him before moving on to the next basket.

"It's mine." Anna cheered.

"I have been told to inform you that it is the food being sold, not the basket, so I'll start it off at five dollars." Taylor didn't want an angry Lorelai screaming through the rest of the event like she threatened to.

"Five dollars." Kirk raised his hand.

"Five, do I hear ten?" Taylor looked around.

"Thomas." Anna hissed at the teen that was standing across from her. She invited him along, so she wouldn't have to have lunch with a weirdo. He didn't turn his head to acknowledge that he heard her. "I made that damn lemon bar and I don't even care for lemon." She growled.

"Five going once… five going twice.." Taylor counted.

"You're dead." She glares at the side of Thomas's face.

"Ten." A voice shouted from the back.

She turned her head to see Jess standing there. He had on a tan coat over a green shirt and jeans. She looked back at Thomas who still wasn't looking at her but had a large smile on his face. Kirk and Jess went back and forward until it got to ninety and Kirk stopped. Jess went up to collect the basket. Anna ran over to Thomas. "You knew?"

"He came up to me before this and asked if I would let him buy the basket." He told her. Jess knew he didn't have enough money to outbid the rich kid, so he figured asking was the best option. He also wanted to double-check that Thomas wasn't interested in Anna.

"That's why you made me put on something cute." She was going to wear her sweats but he insisted on her dressing up. She was wearing a jean jacket over a skull and flower satin tank top, black jeans, and black heeled combat boots. She dug out her aristocrats' purse from her Tristan box and her favorite pair of sunglasses that were sitting on top of her head.

"Yeah, part of the deal was I still get a piece of that lemon bar." He smiled at her shocked expression. He didn't blame her, Jess was a hard guy to read.

"This is a part of our deal, now scram." Jess held out a piece of the dessert to the teen.

"See ya, I got to meet Roger and Eleanor. Or maybe I won't and they can be alone." He wiggles his eyebrow as he walks away.

"I know he got in because of his family. But, he's passing classes." Jess pointed at Thomas. He liked the guy just fine but he seemed like a total airhead.

"He's good at memorizing things. Long enough to take the test at least." She told him.

"Well… you ready to go?" He held up the basket.

"Sure." She hooked arms with him and walked to the bridge over the lake. They sat down in the middle. "How come you wanted to buy my basket?"

"You really are going to make me say it?" He sighs.

"I would like for things to be clear." She nods.

"I like you and I wanted to take you out so I bought your basket." He looks down at the pond.

"Never took you for a scared cat." She teased.

"What?" He turns his head towards her and narrows his eyes at her smiling face.

"You could have just asked me to go out, but then I could have said no. So, you had to find a way where I would have no choice but to go out with you." Her smile widened.

"You know what I lied. I bought this basket out of pity because it's pathetic that you had to bribe someone to buy your basket." He glares.

"You think I'm gorgeous. You wanna date me. Love me and marry me." She sang.

"What the hell is that?" He stared at her for breaking out in song.

"Miss Congeniality." She screamed at him, feeling offended that he didn't know it.

"You watch that shitty movie?" He scoffs.

"Did you?" She screeched.

"No, why would I? An undercover job at the Miss United States." He scrunched up his face.

"We're going to watch it." She pointed at him. He rolled his eyes but didn't decline it. "Now, let's eat." She opened the basket. She pulled out the thermos and mugs. "It's loaded potato soup." She opens the flask, pours the soup into the mug, and passes him a mug with a spoon.

"What else is on the menu?" He put a spoonful in his mouth. "This is good." He pointed at the soup with his spoon.

"Thank you. We have fruit punch." She grabbed the wine bag that was lined with blue ice.

"Is that a wine bottle?" He eyes it.

"Yeah, but I filled it with punch." She poured them a glass each. "We got turkey wrap, sun chips, and lemon cream crumble bars."

"Sounds good." He tips his cup back, pours more soup into his mug, and grabs a wrap.

"So, is this your favorite place in Stars Hollow?" She looked out at the lake.

"Yeah, it has great memories, like Luke pushing me in." He told her.

"What?" She laughed, picturing that.

"Yeah, right up there." He pointed to the right.

"I'm sure, you deserve it." She giggles.

"I guess." He shrugs. "So, have you read a classic that wasn't school required?"

"Rory and I have a two-person book club. So, I have read a few." She opened the sun chips bag and put it between them.

"What about Ernest Hemingway?" He asked.

"Rory couldn't get through it, so I never did." She shrugs.

"Did you even try?" He looked offended when she shook her head. "If I have to watch that chick flick, you have to read Ernest Hemingway."

"Anyone?" She asked.

He thought for a second before saying, "The Old Man and the Sea."

"Alright, after this we can go to the bookstore." She agrees.

Anna came through the door with a smile on her face and a book in her hands. "Hey." She nodded to her mom, who was sitting at the dining table. She put the book down on the table and the basket by the sink to wash the dishes.

"So, how was the picnic with Jess?" She asked.

"He said he liked me." She blushes.

"What?" Her jaw dropped.

"I can't believe it. I mean I know we get along well. I know I always denied it when someone asked if I liked him but I didn't know if he liked me. Unrequited love is the saddest love. But it's not unrequited." She hummed happily as she washed.

"Are you sure about this?" Lorelai asked.

"What do you mean?" She put a plate in the dry rack.

"I just don't want you to make the same mistake twice." She looks at her daughter's back in concern.

"What?" Anna turns around to face her.

"You went through the bad boy routine already, so why again?" She asks.

"Tristan and Jess aren't the same. Tristan pretends to be someone else and Jess is..." She couldn't believe her mom right now.

"Being an ass from the start." Lorelai cut her off.

"No, he's not the friendliness, but that doesn't make him a bad person." She argues.

"No, but he gets into fights, steals, and draws chalk outlines and lets you take the fall. Don't think I didn't know about that." She pointed a finger at her.

"What, are you going to join the angry villagers?" She put her hands on her hips.

"I'm just concerned because your judgment for men isn't the best." Lorelai crossed her arms over her chest.

"And yours is." She felt like her mom was being a hypocrite.

"Hey, this isn't about me, this is about you." She pointed at her.

"I don't understand, you didn't freak out like this about Tristan. Even after our first break up." She pushed her eyebrows together.

"That was before I knew you were having sex." She didn't want her to make the same mistakes she did.

"So what, do you think I'm just going to jump into bed with Jess? Even if I did, I would make sure to be safe." She never realized her mom thought so low of her.

"It's not just about sex. He is trouble. He's going to lead you down a bad path." She warns.

"I'm some brainless idiot who will do whatever he says. You know what… I think Jess would want me to walk away right now so that's what I'm going to do." She grabbed the book and went to her room.

Lorelai, Rory, Anna, and Emily were eating dinner. "A cigar club. Can you imagine a more disgusting organization to join? Your grandfather now pays money to sit in an enclosed room with a bunch of other men and blow smoke in each other's faces. Twice a week he comes home smelling like a flophouse. So I finally just confronted him. I said, Richard, I know you're going through a transitional period here and I encourage you to try out new things, but this seems completely out of character for you…. I'm sorry, am I boring you?" Emily asks when she saw everyone staring at their plates.

"No, you're not," Lorelai reassured her.

"Sorry, Grandma." Rory and Anna apologize.

"So, how are things at the inn?" She looks at her daughter.

"Fine, the same." She smiled.

"And Rory, how's that boyfriend of yours?" She turns to her oldest granddaughter.

"He's good." Rory nods. She didn't know what to say with the heavy tension between her mom and sister.

"Well, that's nice. How have you been, Anna?" She turned to her more talkative granddaughter.

"Everything is the same with me. No new addition, yet at least." She shot her mother a tight smile.

"Okay…. Lorelai, anything new with you?" She turns back to her daughter since Anna wasn't making any sense.

"No, nothing. It's been pretty quiet around the house lately." She shot Anna a glare.

"Well, sometimes quiet can be nice. Soothing. You can hear yourself think. Alright, what's going on with you two?" She put down her fork and knife to point at Lorelai and Anna.

"Nothing." Lorelai shrugs.

"It's not nothing. You've both been sitting here all night, not saying a word and not even looking at each other. Are you in a fight?" She asks.

"I'm not." Lorelai looks down at her plate.

"What? You're the one that started the fight." Anna let out a bitter laugh.

"So, we have one argument and you freeze me out all week." Lorelai scoffs.

"What's the point in speaking if you don't trust my judgment on things?" She shrugs.

"Not on things, just a boy." She put up a finger.

"A boy?" Emily asked.

"Jess had a tough time adjusting to Star Hallow. You want to hold one night against him for the rest of his life." She shouts.

"Jess, who's Jess?" Emily asks.

"Luke's nephew," Anna told her.

"He is trouble. It was one thing when you were friends with him, but now that it has become more it needs to stop." Lorelai slammed her hand down on the table.

"You know, you never liked Dean at the beginning." Rory tried to help her sister.

"That's because I didn't know him." She said.

"You don't know Jess. You think you do, but you don't. If someone caught you on a bad day, they say you're a bit..." There was a reason she didn't want to have this talk.

"HEY!" Her mother yelled before she could finish.

"All I'm trying to say is that you can't know someone off one night and things you hear around town." She crossed her arms.

"Anna, if your mother thinks this boy isn't appropriate company for you then you need to listen to her," Emily spoke up.

"There, thank you, Mom." Lorelai pointed at her mother.

"I'm going to my room." Anna stood up to walk to her room in Gilmore's manor. She picked up the phone. She thought about calling Lane but didn't want to deal with Mrs. Kim, so she called Henry. She sat on her bed while the phone rang.

"Hey, Anna." He answers.

"Hey Henry, how was your date with Lane?" She asked.

"I didn't go on the date." He said slowly.

"What?" She was shocked.

"I like Lane, but I can't keep sneaking around. Especially when her parents would like me. I want to be able to go on a date without needing a decoy. I want prom to be a special time, not a stressful time that is why I asked someone else." He explained.

"I get what you mean." She felt bad for Lane, but she understood Henry's point. It wasn't fair to him. "How did she take it?"

"I was actually about to call you to check on her for me. She was nice about it but I could tell she was crying." He told her.

"I'll sneak in her window later. I doubt Mrs. Kim would let me in. Probably will think I did something to make Lane cry." She didn't want to get banned from seeing Lane.

"I hope she can find a guy that she won't have to sneak around with." He said.

"Me too." She sighs.

The door opened. "Can I come in?" Lorelai stuck her head in.

"I'll talk to you later, Henry." She hung up the phone. "If you didn't hear that was Henry, not Jess."

"I've come to reach an understanding." Lorelai sat down on the bed next to her. "I don't wanna lock you up and throw away the key."

"That's a relief because I don't want to be a prisoner." Anna didn't know that was going to be an option.

"Your judgment means something, especially to me. I can't be your eyes and your ears and your brain." She knew she raised a strong woman.

"Then why did you say those things?" She asked.

"I got spooked. I know it violates the fabulous cool mom clause we're supposed to have going but I did and I'm sorry." She grabbed her hand to squeeze it.

"I get it. You find out I'm not a virgin and I'm starting to see this guy that no one has anything good to say about. It would spook any parent. I know I'm infatuated with him, but I wouldn't do anything out of character with him like drugs or a crime. When we hang out it's watching movies, talking about books, and eating." She didn't want her mom to worry when she was out with him.

"I know, I trust you. I saw a teenage me getting on your dad's bike and freak out and it turned me into my mom. She agreed with me tonight. My mom agreed with me tonight. " She made a face.

"I'm sorry." Anna rolled her eyes, laughing.

Later that night, Lorelai, Anna, and Rory walk through the front door. "I need a shower," Lorelai shouted.

"Don't be so dramatic." Rory closed the door.

"I agree with you a hundred percent." She imitated her mother's voice.

"Go upstairs." Anna pointed up the stairs

"Find a movie, I'll be down in a minute." She took off her coat and purse.

"Okay." Rory and Anna did the same.

"I agree with you a hundred percent. I may have to shave my head also." She shouted as she climbed the stairs.

"So, everything's good?" Rory asks.

"Yes, we have an understanding." She reassured her.

Rory and Anna were climbing the tree by Lane's room. "Lane," Anna whispered as tapped the window.

She opens the window in her pajamas. "Did Henry call you?"

"Yes, we can call him the idiot if it makes you feel better." Anna smiled.

"No, I was an idiot. I appreciate this guys but I don't feel like talking to anyone right now." Lane went to close her window.

"But, we got ice cream and brownies." Rory taps Anna's backpack.

"Whip cream, hot fudge, and sprinkles," Anna added.

"Alright." She opens the window back up. They climbed in and made their sundaes.

"I'm sorry," Rory apologized.

"It's my fault. I lost a good guy for no reason. My mom's calling all the Cho in the phonebook." She told them.

"You told her." The siblings said in surprise.

"Yeah, now she's upset too. It's so stupid, I should want my mom to like the guy I'm dating." She let out a bitter laugh.

"It's just a prom date, not a wife. Maybe you guys can still get back together." Anna wanted to lift her spirits.

"No, he wants to date other people, he has that right. He was never officially my boyfriend, even though he felt like it." She sprayed more whip cream in her bowl.

"There be another," Rory told her.

"They would be lining around the block if they weren't scared of your mom." Anna teased.

"Oh yeah, cause Kirk wanted my baskets. So, I got the top choices in town." Lane laughed.