"The problem with life is that it is rarely how we picture it. Tell me what you pictured."
"Something completely, and totally unrealistic," she admits.
"This is me you're talking to," he reminds her.
"I pictured a life like my grandparents. I pictured a big life, I guess."
He shakes his head, "You would never be content with that. You would be miserable. Big houses are lonely when you're alone. You would just be trying to be someone that you're not. He isn't right for you. He isn't good enough for you. He has made that abundantly clear. If he was good enough for you nothing would stand in his way. He would do whatever it takes to be with you."
"It doesn't really matter, does it?"
"You're having his kid, aren't you?"
"Maybe," she shrugs.
"Rory, what do you mean, maybe?"
"I ended things. That isn't true, because we didn't have a thing. It was an ongoing fling. Anyway, I was hurt after it was all said and done. I was trying to find my niche, and I couldn't. I was flitting from one thing to another. One weekend I was at Paris's, and I went to a party with her. It was a bunch of super successful, rich people. I felt unworthy, so I just kept drinking, trying to numb whatever it was I was feeling. I ended up doing the walk of shame back to her place the following morning."
"When did you become so reckless? What happened to the girl who made pro-con lists before even considering what movie to see?"
She shrugs, "I don't know what happened to her. I know I have to stop being reckless. I am having a baby. I am far too old to be acting this juvenile. I just don't know how I am going to do this."
"You can do this," he insists.
"How can you be so sure?"
"Because you're Lorelai," he answers.
She furrows her brow, and scrutinizes his facial expression, in an attempt to decipher his meaning.
"You are strong, and fierce, and brave. You can do anything, you just have to keep telling yourself so."
"What am I supposed to tell my kid? How do I explain why they don't have a father?"
He stops, and breaks eye contact, "How long are we going to do this?"
"Do what?"
"Pretend that we're finished. How long are we going to act as if we're satisfied with the end?"
"What do you mean?"
"We aren't naïve kids going two different directions anymore," he reminds her.
"What are you asking me?"
"I am trying to tell you something," he admits, struggling to find the right words.
"What are you trying to tell me?"
"It was always you."
She falls silent. She allows time to pass as she processes what he has said. It makes no logical sense. Why would he say such a thing? She is knocked up by someone else. She is thirty two, and has nothing to show for herself.
"Why? Why would you want me?"
He shrugs, "The heart wants what the heart wants."
"It is completely illogical," she points out.
"Love often is."
"When did you become a sap?"
"Rory I am asking you if you would consider…"
She cuts him off, "Yes."
"Yes?"
"Why would you want to consider it, though? I am knocked up by someone else. I am living above Luke's diner. I have a mediocre job, and am still stuck on the right ending for my book. I have wasted so many opportunities, because I let my ego over inflate my head. I acted like a privileged kid with a trust fund to fall back on."
"You do have a trust fund to fall back on," he points out.
"That is the problem. I have always had a safety net. Someone has always been around to bail me out. Now, all of a sudden I realize that I needed to do it on my own. That is why my mother stopped talking to me when I stole a yacht. She saw then, what I am only seeing now. I screwed up. I should have been able to handle it on my own. I was an adult. I also should have seen that Logan was never right for me. He is the springboard for so many questionable decisions. Did I stroke out, or something? Why was I so okay with being the other woman? In what world did I lower my standards so much, that I am okay playing second fiddle to some blonde heiress bimbo? Why would you want me? I am not worthy of…"
He cuts her off, "Stop!"
"You can't even argue. All of it is true."
"You are an incredible person. You're right. Having a safety net has held you back. You haven't had to be successful, because it wasn't your only option. Now it is. You either sink or swim."
"I am completely drained physically, and emotionally."
"I have been reading the articles you have been writing lately, and they are on point."
"I doubt it. I am usually up until some ridiculous hour finishing my pieces for the Gazette."
"Give yourself a break. Not everyone can be successful right out the gate."
"You have it. What if I don't have it?"
"You have it. Anyone who thinks otherwise is a fool."
"How do you know?"
"It doesn't get polished, until you are at rock bottom," he points out.
"What exactly are you suggesting, anyway?"
"I can work from anywhere," he reminds her.
"You hate Stars Hollow."
"It has become more appealing lately," he admits.
"Because of me?"
"Yes."
"You grew up, and I regressed," she admits.
"Let me show you the ropes, Gilmore."