Top 10 Times The Guys From Gilmore Girls Were The Worst

Sookie and Jackson’s first date evolves into a double date when Jackson is forced to drag along his pesky cousin Rune. Lorelai, being a good friend, agrees to be Rune’s blind date, even though she’s evidently out of his league. Yet, it’s Rune who inexplicably has an issue with Lorelai’s appearance. Seriously, dude? In addition to being rude, Rune is anything but discrete, seeing how Lorelai overhears every word that comes out of his big mouth. Rune spends the evening looking at his watch and treating Lorelai like she has the plague. Meanwhile, Lorelai winds up chatting with Luke for most of the night, which thankfully pushes Rune to finally leave Sookie and Jackson alone.

It’s rarely a good sign when Emily Gilmore tries to set you up with somebody. Unlike Rune, Graham at least seems interested in Rory when they first meet, but he ultimately ends up being a total putz. With some slight hesitance, Rory decides to go out with Graham. Scratch that. She goes out with Graham and his beer buddies – and you know it's always totes fun to be the only sober one in a group! Graham dedicates most of his night to talking with his bros about sports, leaving Rory alone at a table. Then when Graham finally acknowledges Rory, he has the nerve to tell her to live a little and endorses drunk driving. A putz, indeed.

Marty starts off sympathetic. After all, many of us can identify with liking somebody, knowing full well you’ll perpetually be in the friend zone. Rory and Marty have a falling out after he confesses his true feelings, but she rejects him in favor of Logan. In Season 7, it’s revealed that Marty is now dating Rory’s new friend Lucy. For some reason, Marty feels the need to lie to Lucy, pretending he’s never met Rory. This just shows that Marty hasn’t matured since Freshman year and he’s still hung up on a girl who’ll never reciprocate his feelings. When the cat inevitably comes out of the bag, Marty destroys his relationship with Lucy while nearly ruining Rory’s friendship with her.

Following a bad date, Rory happens into a meet-cute with a fellow student named William. While their encounter is brief, Rory senses a spark between them, and asks him out for coffee. As if Rory’s night couldn’t get any worse, William straight-up turns her down with no explanation. William resurfaces in a later episode where Rory believes that he’s been telling people about “the laundry room incident”, leading others to believe that she’s obsessed with him. As it turns out, William was actually talking about another girl who really was stalking him. Regardless, that doesn’t change the fact that he straight up rejected Rory friggin’ Gilmore! Who does that?

Despite wanting to distance herself from the upper-class lifestyle her parents have always imposed, Lorelai is drawn to Jason Stiles, a business partner of Richard. Mixing business with pleasure is often a recipe for disaster, and it's no different here. Initially, Richard and Jason conspire against Jason’s father, Floyd Stiles. When Floyd catches wind of this, he strikes up a deal with Richard that’ll leave Jason in the dust. We can certainly understand why Jason would feel betrayed, but he takes things too far when he decides to sue Richard. For all the issues Lorelai has with her parents, she draws the line at litigation. In the end, Jason chooses a lawsuit over Lorelai

April is widely seen as a shark jumping moment, given how others respond to her. Giving Luke a 12-year-old daughter he never knew about was already pretty forced, but what’s even more forced is that Luke doesn’t immediately inform his fiancé. Luke keeps saying that he’ll tell Lorelai when the time is right, but of course she finds out from someone else. She takes the news better than most would, and is even open to postponing the wedding for Luke. When Luke refuses to meet Lorelai’s ultimatum, though, she winds up sleeping with Christopher. While Luke isn’t the only person at fault here, a lot of heartbreak could’ve been avoided if he just communicated with Lorelai.

Jess would later develop into one of Rory’s healthier love interests, but that’s where he started. Early in their courtship, Jess was either pushing her away or pressuring her into something she didn’t want. Case in point, a party where Jess attempts to have sex with Rory, who’s made it clear she isn’t ready. This results in one of their biggest blowups, as well as a fight between Jess and Dean. Jess subsequently leaves Stars Hollow without giving Rory a proper goodbye. When Jess returns the following year, he seemingly has a breakthrough when he tells Rory he loves her. The minute Jess reenters Rory’s life, however, he runs away again, which becomes a recurring habit.

In between one of his breakups with Rory, it’s revealed that Logan slept with multiple women and sucked face with another. To Logan’s credit, they were technically on a break and he does fully commit to Rory after some turbulence. Logan’s growth as a romantic partner is largely undone in “A Year in a Life”, however, where he engages in an ongoing affair with Rory, despite having a fiancé. As if cheating on a woman who loves him isn’t shallow enough, Logan seemingly feels no guilt about his unfaithfulness. Of course, Rory isn’t much better since she has a boyfriend she keeps forgetting to break up with. It doesn’t help that Logan’s act of infidelity might’ve resulted in Rory’s pregnancy.

Rory gets a lot of flak for sleeping with a married Dean, as she should. For many, this was the point where Rory becomes a much more self-absorbed, self-destructive character. But Dean carries just as much blame, if not more. After all, he’s the one who married Lindsay, despite still having feelings for Rory. He’s the one who continually led Lindsay on, despite clearly not being ready to be a husband. He’s the one who kept tiptoeing around the elephant in the room, making it all the more devastating when he committed adultery. While Dean would learn from his mistakes and have a more successful second marriage, the way he treated Lindsay remains inexcusable.

Before we get to our top pick, here are a few dishonorable mentions:

Jackson Lying About His Vasectomy
“To Whom It May Concern”

Tristan Generally Being a Jerk to Rory
Various Episodes

Taylor Always Being a Control Freak
Various Episodes

Trevor’s Date with Rory
“The Fundamental Things Apply”

Luke’s Ridiculous No Cell Phone Rule
Various Episodes

Honestly, was anybody on Team Christopher? After impregnating Lorelai as a teenager, he was rarely around for her, or Rory. Granted, it's partly because Lorelai refused to get married. Even years later, however, Christopher remains a mostly absentee parent, both to Rory and his other daughter Gigi. Worst of all, Christopher always reenters Lorelai’s life just when she’s starting to find happiness with someone else, namely Luke. Christopher has been pressured by others into interfering with Lorelai’s love life and sometimes Lorelai has even come to him. Chris never considers what’s best for Lorelai, though, jumping at every opportunity to take advantage of her. Whenever Christopher showed up, we trouble was following.