Prologue:

Emily allowed herself to savor her triumph. It had taken some doing, but her plans had come to fruition. Rory's relationship with that unsuitable boy had come to an end. Sure, she seemed upset when Dean had unceremoniously dumped her, but soon Rory would be caught up in a new romance and forget all about him. Indeed, the Huntzberger boy had shown a gratifying interest. Now there was a young man worthy of her granddaughter.

Meanwhile, Rory walked along the deserted streets of Stars Hollow feeling alone and depressed. Last night had been a total disaster. She hadn't meant to hurt Dean, but events had just gotten out of hand. Replaying the evening in her head, Rory felt a stab of irritation at Dean. It's not my fault Grandma and Granddad threw that party, she thought. I didn't ask them to invite all those boys. It's not as if I'd kept him waiting for hours, it was just a few minutes. He didn't have to overreact like that and dump me in front of Logan and his friends.

A shadow fell across her path. She looked up and saw her ex-boyfriend.

"You!" she said angrily. "What are you doing here?"

He took her hand and said, "I'm sorry Rory, I never meant to hurt you. I was wrong to break it off."

Rory yanked her hand back. "You dumped me and think you can come back here and apologize, and I'm supposed to take you back?" she snapped.

"Please give me another chance," he said, giving Rory the full puppy dog eyes. Her heart melted. They kissed.

Six Weeks Later:

Emily was puzzled. Less than an hour ago, her daughter and granddaughter had arrived for the usual Friday Night Dinner. However, instead of Lorelai's usual tedious, juvenile banter, both mother and daughter seemed uncharacteristically serious.

Then things started getting strange. First Rory started stammering something about being sorry to disappoint her and Richard. Then Lorelai, looking smug, made several cryptic remarks about keeping tomorrow free.

Emily snapped, "Stop being obstreperous and tell me what's going on!"

"What Rory is trying to tell you Mom, is that she's getting married this Saturday," Lorelai said, relishing her mother's confusion.

Emily reeled from shock. "But why? Why does Rory have to get married immediately? Why does she have to get married at all?" Emily said.

Lorelai simply smirked.

"I, I, kinda have to get married, Grandma," Rory mumbled. "I'm pregnant".

The full meaning of her words sunk into Emily. Rory had to get married. That could only mean one thing. She had failed. Her brilliant plan was too little, too late. Now Rory would be forced to marry that yokel instead of gracing the home of one of Yale's finest. She gave Rory a fierce look.

"I didn't plan for this," Rory said apologetically. "We ran into each other, and it just kinda happened."

Emily felt faint. Catching a glimpse of Lorelai's smug expression, she quickly pulled herself together. Lorelai expects me to go into hysterics, but I won't give her the satisfaction, Emily thought. Her mind raced. This doesn't have to be a disaster. After all, Dean is a polite, pleasant boy, unlike some she could name. Yes, this could work out.

Naturally, Dean would have to abandon the silly idea of working in the trades, but Rory had mentioned that he'd been accepted into Connecticut State and completed a semester. He'd simply have to go back to school, then Richard would find Dean a suitable post in his office. Fortunately, Dean had always been extremely eager to please Rory, so Emily didn't anticipate any serious objections.

Emily found herself warming to the idea. They'd live in the pool house under her watchful eye, at least for the first few years. Then she and Richard would find them a suitable home, preferably nearby. Rory could spend her days helping with the DAR events and other charities Emily deemed appropriate for a woman in Rory's position. Emily, of course, would supervise the child's education – no public school for her great grandchild. Perhaps they would consider adopting the surname 'Forrester-Gilmore'.

Giving Lorelai and Rory her most gracious smile, Emily said, "I won't pretend to be thrilled my granddaughter is having a shotgun wedding, but we're Gilmores. We'll manage. I assume the Forresters are in agreement with this marriage?"

"Um, no, Grandma," Rory said in an oddly sheepish tone. "I'm not marrying Dean, I'm marrying Jess."

Emily fainted.