5x22 & 6x01: "Luke, Will You Marry Me?"
Luke gathered his thoughts. He had been trying to follow Lorelai's rambling explanation for the last few minutes as they sat alone in his closed diner. From what he could gather, Rory was actually dropping out of school, on account of some emotional, mental….. baggage, he wasn't sure what it was, still. Finally, the diner owner found his voice. "OK, I'm sorry. I have to jump in here. I know you think you have this thing handled, but I can help." He sighed long and low, gathering his thoughts. "First off, we call Yale, and we tell 'em something like…. uh…. Rory had a chemical imbalance and she was mentally out of her mind when she told them she was…. dropping out. Then, we get her out of your parents' house – whatever way we can – lock her up in her room, with you, cuz you can talk her into this; you can talk anybody into anything! And if worst comes to worst….. we will drive her to school, every day, and we will follow her to class, and camp out there to make sure she goes! I'll take morning classes, you take afternoon classes, or the other way around, if it works out better with your schedule, and…. I know there's a few kinks to work out, and the kidnapping thing might be a little problematic, but either way, she is not quitting school! This was her dream! I am not gonna let this happen!"
Luke paused to catch his breath after his diatribe to find Lorelai gazing at him almost lovingly. "What?"
"Luke, will you marry me?"
As Lorelai would tell it to friends and family later: "In that moment, when I realized how much he cared for Rory…. That was it. Suddenly…. I knew I was ready….."