AUTHORS NOTE: Most of the story is still the same. The only thing I changed was the fact that Rory and Jess never dated in high school and that Jess is currently a Yale student. The characters will, from time to time, act ooc due to the fact that this story is based on real life. And for the sake of telling the narrative correctly, the characters may need to deviate from what their canon versions may be like.

"Look Rory, I really suck at this whole boy thing alright? I mean look at my dating history. The guy I'm currently dating is more emotionally needy than I thought. We're on and off almost every other week. He can't even make rent without his bum of a roommate. And he also happens to be my former editor in chief. The last really good thing I had going for me...well I completely ruined that by sleeping with my professor who was old enough to be my well-"

"Yes Paris, I remember."

In the midst of it all, Rory called the one person she knew could give her an answer straight up. They met up at the pub, Rich Man's Shoe because although Rory was not an avid drinker, tonight she really felt like she needed one.

"Anyway. I'm really the last person you should be talking to about this."

"Yeah but...I need some practical advice about this. You're the only one I trust with this. I don't know what to do."

"Practical advice huh?"

"Please."

"Wait. I need another beer. Excuse me miss?" Paris called out to the bartender.

It was a Saturday night and the pub was packed with students celebrating their last week of the semester. The place was alive with the sounds of students' cheering and of their drunken laughter.

"Excuse me!" Paris exclaimed. None of the bartenders could really hear her over the noise. "Jesus, whose ass do I have to kiss to get a drink around here?"

"Can I help you?" A bartender finally replied.

"Yes you can. 2 more Stellas if you can please, and quickly."

"I'll just check around back."

"Well, we'll just be here and if you could be back before we grew beards or something, that would be really great." Paris snidely remarked.

"Paris! Don't be so rude. She's just doing her job."

"It would help if she did it better."

"The place is packed Paris. If you haven't noticed people around here are celebrating. I mean, look at them. They're so happy."

Rory looked around at her fellow students laughing, celebrating and just having a good time.

"I was never one for irony." Rory said.

"Oh. Well did you want to go somewhere else? Somewhere where people are…I dunno. Less happy? Or more emotional? We could go to a poetry reading."

"God no." Rory giggled. "I can't take anymore drama. And well, I guess with how terrible I feel I just need to be surrounded by…people like this."

"Alright. Well, look I know how badly things turned out for you and Dean. The last time you followed your heart, you ruined a marriage."

"Thanks."

"Seriously. You were a mess that time and I get it. I get that back then he was your first and only boyfriend and when he left you for Lindsey-"

"Do you have a point in all this?"

"My point is-"

"Here are your two beers." The bartender interrupted.

"Thank you." Rory said. "Anyway, your point is?"

"Logan."

"Why?"

"Because he buys you coffee stands in the morning. He gives you Birkin bags that haven't even been sold to the public yet. His dad is CEO of a freakin newspaper. He could literally publish a feature article that's just about his love for you."

"Well, he's obviously not going to do that."

"But do you get what I mean." Paris asked seriously.

"So it's about the money? Like Logan could buy the entire Yale University but Jess needs a scholarship to stay in it?"

"It's not about the money. Logan...he can give you everything you want. Material or otherwise."

"And Jess can't?"

"I don't know that he can't. But Logan, without a doubt, he can and he will. And he loves you. And you love him."

"I do." Rory quietly remarked.

"And you know what it's like to be with him. You know that he's a good boyfriend. Well, okay not the best but he's good to you. I'm just saying, don't ruin your relationship with Logan for something you're not certain about. You two have a good thing going. Please just don't Eddie Fisher this."

"Huh? Ooohhh because he broke up with Debbie for Elizabeth and it failed anyway!"

"Yeah. So, stick with Debbie."

"That sounds wrong."

"You know what I mean. That's just my two cents on it but it is ultimately your choice. This time, follow your heart with your head, alright?"

"Yeah." Rory wistfully smiled at Paris. "Alright."