Family Portrait

Author's Note: Thank you to those who reviewed. I'm still not done, and the ideas keep coming for this chapter. Telling Emily and Richard Gilmore is going to be a ball. Keep up the reviews!

Chapter Twenty-Two: Telling Emily Gilmore

Telling Emily and Richard Gilmore that she was engaged wasn't supposed to be this hard. She'd woken up that morning, Jess still fast asleep by her side, in the apartment above the diner and had promptly checked the time. Her grandparents would just be finishing breakfast, it would be the perfect time to tell them.

When she had gotten on the phone with her grandmother though, there had been no getting her to listen. Emily had gone on and on about throwing Rory a baby shower. She hadn't been able to get one word in before Emily jumped in about something else. In the end, all she had gotten out of the conversation was that she was going to Friday night dinner with her mother and Luke.

"This is impossible," she sighed, shaking her head. Jess stirred in his sleep and rolled over. Rory was amazed that her mother had actually suggested she and Jess stay together above the diner that night. Since she had gotten home from the hospital, Lorelai had insisted that Rory stay in the house and forget about her room at the Inn.

"Do you Gilmores ever sleep?" Jess mumbled tiredly, sitting up slightly in bed.

"Yes, we enjoy our sleep very much thank you," Rory replied, smiling at him.

"Tell me why you're awake then," he groaned.

"I needed to call my grandparents," Rory clarified, "Tell them about the engagement."

"Do we really have to?" Jess wondered, "We can always just get married, and in a couple of years, they'll ask and you can tell them."

"We have to tell them," she told him, and then leaned over and kissed his cheek, "I'm going to get coffee."

"Mmm…" Jess rolled over again, going back to sleep. Rory smiled and stood up, heading towards the door of the apartment. She could get used to this, being with Jess for the rest of her life. Of course, considering she was getting married to him she better be able to. This feeling of permanency though, it felt good to Rory. It didn't scare her at all, and she hoped that Jess felt the same way.

Walking down into the diner, she paused seeing the morning rush, and looked down at herself. She couldn't help but let out a little laugh. There was no doubt she was a sight to see. Her short, curly hair a mess with pajama pants on and just a white tank top. Spotting her mother at the counter, she went over and took a seat next to her. "Morning."

"Good morning oh daughter of mine," Lorelai grinned, "Sleep well?"

"Mm-hmm…" Rory nodded, and grinned at Luke as he slid a coffee over to her. The twenty-three year old received the off look from the occasional customer, but she didn't let it get to her. After all, it was her prerogative to eat in her pajamas if she wanted to.

"So, do Emily and Richard know that their dreams of you marrying to the likes of the prestigious Tristan DuGray are shattered yet?" Lorelai wondered.

"I tried to tell her this morning, but all she could talk about was throwing me and Haley a baby shower," Rory told her mother, "What was I supposed to say?"

"Hey, grandma, you better make it an engagement party at the same time," Lorelai offered.

"Why can't you just out and say that you're getting married?" Luke wondered.

"You do remember this is Emily and Richard Gilmore we're dealing with right?" Lorelai raised a brow at her husband, "Two people who when we announced we were getting married simply said, 'Oh, well, that's nice' and continued to eat their supper."

"So?" Luke shrugged.

"Oh, you still have so much to learn," her mother shook her head, and then turned back to Rory, "You do realize what kind of pressure this is going to put on poor Liza, right?"

"What are you talking about?" Luke was looking at his wife as if she was insane; "They love Liza."

"Right, they love Liza," Lorelai nodded, "But they put all their hopes and dreams into Rory to not disappoint them like me, their only daughter, did. Then, she gets pregnant at eighteen, ruins their plans for her. She goes to Yale though, and then when she gets pregnant again, there's a glimpse of hope, this time it's a DuGray, a name that carries value. Once again their hope is dashed because she's not going to marry him, but instead, the hooligan who ruined their plans in the first place. They're really going to be rolling out the red carpet for Jess.

"They still have a glimmer of hope though, a slight chance that at least one Gilmore will carry the name with honor. Their great-granddaughter, Liza. So, when the news finally breaks that Rory is marrying Jess, they invite us over for another Friday night dinner. But, this one is different. There are five-year-old boys, great-grandchildren of all their good friends, suitors for Liza. They'll be an arranged marriage, and they'll kidnap Liza in the middle of the night and lock her in a tower until she's old enough to marry the man they picked out."

Rory and Luke stared at her as she dramatically gave her monologue. When she was done, she took a sip of her coffee, and shook her head. Rory laughed lightly, knowing her mother was exaggerating, as always, when it came to talking about her parents.

"You're crazy," Luke shook his head gruffly, and went alone to serve other customers.

"I'd have to agree with Luke on that one mom," Rory said, still grinning.

"You just wait," Lorelai told her daughter, "If anyone knows my mother and father better than me let them speak up and say different, but I was raised in that house and trust me on this. Emily and Richard Gilmore will not rest until Liza's future is set in stone, so they won't have to worry about little mistakes like mine or yours."

"Oh, quit the drama queen routine Lorelai," Christopher chuckled, sliding into a seat next to his daughter. Rory offered her father a small smile, and moved off her stool to give Georgia a hug.

"Chris!" Lorelai exclaimed, "Your daughter is currently engaged to Jess Mariano, now tell me I'm being a drama queen."

"Oh," Chris then turned to look seriously at his daughter, "In that case, beware of the wrath of the Gilmore clan."

"I think I'm going to take my coffee and breakfast upstairs," Rory shook her head, "Where sanity is more likely not just optional."

"Right, Jess is sane," Lorelai chuckled, "You just want to have crazy morning 'I'm engaged' sex!" Rory rolled her eyes at her mother, used to this behavior, Chris coughed trying to suppress his laughter, Luke glared at his wife, and the rest of the diner started at them in silent interest. Gossip would be flying around the town about Rory and Jess' apparent engagement in no time.

"Well, then just make sure not go upstairs," Rory grinned, disappearing up the stairs with no further comment on the matter. Just let them wonder what was going on up there between her and Jess.

(The Elder Gilmore mansion)

"Jess and I are engaged," Rory announced to the closed front door of her grandparent's house where she found herself standing. It wasn't even a Friday night, but she had forced herself, Jess and Liza to pile into the car and head over to Hartford for a visit.

"There, you said it," Jess said, he was leaning against the wall, his hands in the pocket of the suit jacket Luke had forced him to wear, "Can we go now?"

"No, Jess!" Rory frowned at her fiancée; "I have to tell them that we're engaged." She sighed looking over at Liza who was sitting on the steps playing with her Leap Pad as she had been for the past ten minutes they'd been out there.

"Then just knock on the door and tell them," Jess coaxed. Rory could tell he was trying his hardest to be patient with her. This dinner thing was really something he didn't want to do, but he was doing it because she wanted him too.

"All right," and with that, she reached out and rang the doorbell.

Within seconds, the maid appeared at the door and regarded them carefully, waiting for someone to tell her who they were and what they were doing at the Gilmore residence. Especially since Rory was sure her grandparents weren't expecting any company tonight.

"I'm Rory Gilmore," she informed the maid, whom she'd never seen before, "Can you tell my grandparents that I'm here to see them."

The maid nodded and led the two adults and Liza, who help onto Jess' hand now, into the house and took their coats before rushing off to Richard Gilmore's office. Rory seemed relieved that she would face her grandfather first, maybe he would at least be more civil than her grandmother.

"Rory?" her grandmother's voice rang through the hall, shattering all hopes that Richard Gilmore would be there to calm his wife down when she found out who Jess' companion of the night was. "I wasn't expecting you here? What are you doing here?" She paused, turning to Jess, "Who are you?"

Rory looked at Jess, wondering if he was going to be polite and answer, but he was waiting for her instead. He'd never been faced with the wrath of Emily Gilmore before, and he certainly hadn't prepared himself well enough for this encounter with him. None of Luke's stories had prepared him to actual meet the famous Emily Gilmore.

"Grandma," Rory began, "This is Jess, you remember me telling you about him, right?"

Her grandmother frowned, "That horrendous criminal who got you pregnant when you were eighteen? Of course I remember him!" With that, a glare was sent in Jess' general direction.

Just then, Richard Gilmore game striding into the room in his usual distinguished manner. "Emily, you didn't tell me we were having guests," he paused and turned to see Rory, "Rory! What a pleasant surprise! It's always nice to see you and Liza."

Grinning widely at her grandfather, Rory moved foreword to give him a hug. She was happy to have this relief from questioning, this temporary distraction from having to tell her grandparents their big news.

"Who's this young man you brought with you today?" her grandfather questioned.

Before Rory could speak, Liza piped up, "That's Jess. He's my dad and grandma thinks he's a horrendous criminal and mommy and daddy are getting married."

The whole room froze. Rory looked down at her daughter, and then over at Jess who had a small smirk on his face before she finally looked at the shocked expressions of her grandparents.

Them finding out about her engagement had gone exactly as she thought it would. Now, all she had to do was wait for the yelling to start, wait for Emily Gilmore to start going on, right in front of Jess, about how Rory was making a big mistake. How she should be marrying Tristan, and not some hooligan who broke her heart and got her pregnant almost crushing her chances at going to college.

Instead, Emily Gilmore just smiled politely and said, "Well, congratulations."

This time, it was Rory's turn to be shocked. She's see Emily's reaction to her mother's announcement that she and Luke were getting engaged, but she hadn't expected the same non-emotional response from her grandmother with her. She didn't know whether to be happy or not about this.