Rory and Logan first meet around the Yale campus. Along with Marty.

"That's right, you have. You're a talented man. He makes a kick-ass margarita."

They met up again at Rory's dorm when one of his freinds was looking for a girl. Logan: Okay, put my number.

Then they me up in the newspaper office of the Yale Daily News. Where Rory learns Logan's father is esteemed newspaper mogul, Mitchum Huntzberger.

Later she gets Logan on a trip with the Life and Death Brigade.Logan invites Rory to join him in jumping off a seven story high scaffolding. He takes her hand before they leap into the air, holding an umbrella in their free hand. Landing on the ground post-jump, breathless and elated, Rory holds Logan's hand to her heart as it beats wildly from the rush as she looks at him saying, "It was a once in a lifetime experience," to which Logan replies, "Only if you want it to be."

Rory's grandparent'shost a Yale alumni party to introduce Rory to someone worthy young men. Logan comes to her rescue at the party, telling a suitor that he's Rory's boyfriend and they have been together for a year and a half. Soon after Dean breaks it off with her. Though Logan appears at her side, reassuring her that all will be okay. Logan: It'll be okay.

Rory: No it won't.

Logan: Okay, that's it. Back to the pool house men. We have some serious bucking up to do here.

Logan,Colin, and Finn pull a prank on her during one of her classes in which Colin storms in, bellowing that he loves Rory. Logan storms in and a fight breaks out. The fight, which is staged, is broken up by Officer Finn who declares, "Alright, that's enough. Break it up. Rory Gilmore, you should be ashamed of yourself...toying with these boys like this. They used to have pride, they used to have dignity, they used to have balls. Dammit, Gilmore, give 'em back their balls."

Rory offers to help Logan with an article for the Yale Daily News.Meeting him at the pub to exchange notes. They start having a conservation in which Logan confesses that he doesn't find her at all boring.

Logan attends Rory grandparent's wedding. She asks him to dance and questions if he's ever going to ask her out. When Logan's silence becomes deafening, Rory scrambles to gather what's left of her pride, but Logan refuses to let her go. He admits that he's thought of asking her out several times, but that he thought that it wasn't such a good idea seeing that she was girlfriend material whereas he was not boyfriend material, citing that he can't do commitment and didn't want to pretend to her that he could. Rory proposes a "no strings attached" relationship with him.

Taking the initiative, Rory grabs a bottle of champagne, takes Logan's hand and leads him into a secluded room where she surprises him with a kiss. Finding humor in her being dressed like the best man, Logan cracks a joke, saying, "I feel like I'm kissing a guy," which leads to Rory kissing him again, this time illiciting a more pleasurable response from him: "And apparently I had no idea what I was missing." two are caught in the act of making out by Lorelai who has come to fetch Rory for pictures, which then leads to a not-so gracious encounter with Chris and Luke who come barging into the room upon finding Logan alone with Rory.

After Logan fails to call her, Rory calls him the following night proposing to "hang out." He invites her over to his dorm where he is hosting a poker game.The next morning Rory wakes up on Logan's sofa .Then Sookie calls to tell her of her mother's depressed state after Luke breaks off their relationship, Rory hightails it home to Stars Hollow after Logan lends her his limo when she remembers that her car is being serviced.

When she returns to Yale later that night, she drops by Logan's door to bring back his limo.Rory remarks that she'd been hoping for something a little more intimate, Logan jumps to the conclusion that she means that they can only see one another to have sex, which Rory quickly dismisses which leads to Logan pointing out that they can see each other under all sorts of conditions, alone or in a group and that the poker game just happened to be a group thing. Rory deters, realizing that he made a valid point. Logan tells her that he'll be out of town for a few days, but that he wanted to make plans for the night of his return, promising "no group this time."

When he returns from his trip, he stops by her dorm, inviting her out to dinner with his friends only to find her hanging out with Marty, so he invites him along. The night goes great until the time comes to split the check. Logan pays for Rory and offers to pay for Marty's portion when he realizes that Marty is short, but Marty dismisses him and leaves in a huff to find an ATM. Rory goes after Marty.Rory walks back to the dorms with Marty where he confesses that he likes her as more than a friend. Unfortunately, she has to tell him that she likes Logan.

Later that night as she lies in bed, Logan appears at her window, being he'd failed to properly bid her goodnight.After a brief kiss, Rory asks, "I thought you said a proper goodnight?" as she pushes Logan's leather jacket from his shoulders. Logan, again, jokingly, asks if she wanted to change into something more comfortable, hoping for feetsy pajamas. Rory tells him that "she's not that kind of girl" as they make their way toward the bed. He asks her twice if she wants him to go, the second time saying her name to prove his seriousness and when she sternly declares, "No," he says, "Good, 'cause if you think climbing through that window was hard," meaning that, at that point, it would've been harder to say goodnight. Rory says, "Shh," before they stretch out next to one another on the bed.

With mid-terms wrapping up just in time for Spring Break, Logan happens upon Rory on her knees in front of one of the many Yale coffee kiosks.. He orders a coffee and tells the guy serving coffee to "put the lady's coffee on his tab." Rory objects at first, but then happily accepts him buying her coffee. They start to make their way away from the coffee stand as Logan admits to stopping by the Yale Daily News room in hopes of seeing her only to be cornered by Doyle after realizing that she was nowhere around. Logan asks if Doyle ever leaves the newsroom, which Rory answers, "Unfortunately, yes, otherwise I'd be denied the regular pleasure of seeing him in 'Property of Alcatraz' pajama pants. ". Then he pulls her aside, surprising her with a kiss.

Rory then interrupts Logan's kisses to tell him that someone could see, but Logan doesn't care. She goes on to say that a professor could see and at a moment when he's distracted, pull him away to take a mid-term. Logan then confesses that all his mid-terms have been taken, the ones that he couldn't worm himself out of. Rory's asks what he's doing there and questions if he's still going skiing. He explains that he had to drop off an Ethics paper at eleven-thirty first and then he'd be off. Looking at her watch, Rory sees that it's eleven-twenty-five to which Logan says, "We're swimming in time," before kissing her again.

Rory breaks her contact with Logan as she reaches into his bag for his paper, telling him that she wants to see his paper. He tells her that her mind is a mysterious thing as she says that she's dying to know what his take on Ethics is. He refuses to show her his paper, saying that he actually put forth an effort on the paper and it was going from his hands to his professor's. Rory tells him that she's not going to lose it and he points out about her coins from before, which then leads to a small discussion about Hemingway and how the manuscript to one of his novels was stolen. Rory insists that she is right to which Logan asks how much she is willing to bet.

While Logan is away, Rory uses the time spent with her mom to tell her of the newly developing relationship with Logan, gushing about how beautiful and well read he is and how much she likes him.

Rory calls Logan on his cell to tell him that they were both wrong about Hemingway, then asks how his trip is going. He confesses that he cut the trip short complaining that it got boring and there were too many people there he knew so he went back to Yale early. He muses about the serenity and privacy, teasing her saying that it's too bad that she wasn't there. When she ignores his plea, telling him to take her a picture, he flat out suggests, "You know, if by chance you decided to cut your spring break short you could be here with me to see it yourself." And, not too surprisingly, she cuts her vacation short to spend the remainder of her break with him.