Just Gilmore Girly Things: Lorelai's Exes and the Theory of Relativity

Just Gilmore Girly Things is a blog series on my inexplicable obsession with the CW/WB series Gilmore Girls that aired from 2000-2007. This series explores the personal and social connections I’ve made in my repeated watch-throughs over the last 23 years that nobody asked for. 

While I’ve already spent more time than I would prefer talking about straight men in this blog series already, but I think nothing shows that sometimes what makes a relationship seem great is just how terrible the people that came before were. While obviously I have a soft spot for Luke (Scott Patterson), he’s kind of a pretty basic guy. He’s got just as many flaws as he does good qualities, and as a person, he’d probably annoy the crap out of me in real life. 

But seeing who Lorelai (Lauren Graham) chose before, he does seem pretty dreamy. 

Christopher 

He sucks. If you’ve watched the show, you probably don’t need any explanations here, but Christopher (David Sutcliffe) was terrible. 

While he starts off in a sympathetic position, having Lorelai reject his adolescent marriage proposal after she gets pregnant at sixteen and runs off with his baby, he soon makes it clear why that was a preferable decision for her. Without marriage, Christopher isn’t there for Lorelai and Rory (Alexis Bledel) in any meaningful way. He drifts in and out of their lives with no consistency and no responsibility. 

He also knows that Lorelai is waiting on him to get his life together but her parents are continually admonishing her for that choice because it’s not the “proper” way to do things. Chris gets to keep his youth and keep Lorelai in his life—sometimes with the support of her parents—-but never has to actually step up as a parent. It takes Lorelai getting engaged to another man before he starts to grow up and get serious—for another woman. 

Sherry (Mädchen Amick) gets a lot of hate from Lorelai, but she doesn’t really deserve it. Her worst trait is that she’s the opposite of Lorelai: she’s organized, she’s confident but sweet and honest, however that honesty can be abrasive to people (Lorelai) who come from parents who only understand manipulation as a form of communication. She’s also originally only a part of Christopher’s life to make Lorelai jealous. That is until she also becomes pregnant. 

There’s a lot of implications that the pregnancy was a way to trap Christopher into a crumbling relationship, but truthfully, if the relationship was falling apart, why was he having unprotected sex with someone who openly desired children and a serious relationship? And when she leaves him (and their child) for her career, we’re supposed to hate Sherry, but I think she saw Lorelai and Rory and saw Christopher still not showing up for her and their baby and went, Not me buddy! 

Eventually, he learns how to become a single dad (for Gigi, not Rory), but he doesn’t know how to be a husband. He only ends up seeing Lorelai as a prize to be won, and once he gets her, he realizes that he can’t actually give her what she needs to be happy. The best thing he ends up doing for Lorelai is leaving. 

Max

Max. Medina. Max Medina. The young charming private school teacher (Scott Cohen) is the first person to seriously catch Lorelai’s attention outside of Christopher. He’s her first serious adult relationship. 

On the surface, Max seems perfect. He’s smart but not elitist, sensitive but masculine, and he’s head over heels for Lorelai. He’s ready to be Rory’s stepfather, and he’s the kind of guy that Rory would want as a stepfather. But looking deeper, I think Lorelai dodged a major bullet. Like Rory, she’s able to romanticize him afterwards because she never let him actually have any power in her life. 

But Max is actually kind of a jerk. He insists on asking Lorelai to give him a chance, even though she’s concerned about how it could impact Rory and her education. Yes, the first time she breaks up with him is out of insecurity and self-sabotage, but when it results in Rory’s humiliation and his career being jeopardized, that’s when he decides to draw the line—after the damage is done and Lorelai is already on the hook. He’s also prone to letting his feelings control his actions and never holding himself accountable for being in control of them. It’s always Lorelai who’s making him act that way.

But the biggest red flag has to be that he thinks that the solution to toxic cycles of jealousy and miscommunication is marriage. Lorelai is ready to admit that it’s possible that their relationship is over when he proposes to her in the middle of an argument. While he eventually agrees it wasn’t the right reason, he still gives her the proposal of her dreams and urges her to consider it as a solution to their issues. 

Which is why I think Lorelai can never get fully comfortable with him when they’re engaged. He gets offended when Lorelai seemingly keeps forgetting to make him a copy of their key, but in my opinion, Lorelai’s gut was telling her something was off. If they stayed together, it would not have been able to stay a feel good satirical comedy. 

Jason

Probably Lorelai's best match to be honest, but as a person Jason (Chris Eigeman) is ick. 

Jason is the son of her father’s former employer who pushed him into retirement and once spent a summer at the same camp as Lorelai. He re-enters her life twenty years later when he decides to leave his father’s company to join Lorelai’s father, Richard (Edward Herrman), to join his business and become a rival to Jason’s own father.

To describe Jason, he’s your typical grown up geek. While he’s a successful business guy, his whole life revolves around his insecurities. He seeks his father’s approval in business and when that proves to be impossible, he decides to crush him instead. His whole self-worth is tied up in his work, so he’s debilitated by anxiety and stress, to the point of insomnia. But then again, that’s probably what Lorelai relates to most.

Lorelai sees him for the first time after Emily (Kelly Bishop) shows up at Lorelai’s house to announce in devastation the party she’d been hired to cater for Richard and Jason’s business launch was cancelled last minute. Lorelai shows up at Jason’s office to confront him for hurting her mother’s feelings after she can’t get him on the phone. But when she arrives, he brushes off her concerns because he becomes determined to get her to go out with him. 

While in the early 2000s the trope of the persistent suitor was still considered romantic, now we’re aware that it’s a little more insidious. Like with Max, Lorelai isn’t sure if she should get involved with him at first, but he continues to pursue her. He figures out that her mother is her weak spot and leans into it blatantly.

“Your mother would hate it.”

“My mother would hate it,” she replies, unable to keep a smirk from her face. 

But Lorelai is still trying to keep some peace in her relationship with her parents for Rory’s sake so when she finally agrees to go out with him and realizes she likes him, she wants to keep it a secret. While I agree with Jason’s resistance to keeping secrets, I can’t help but suspect that he actively opts to use manipulation and insecurity to prove his point when he takes “his friend Crystal” to an event with her parents in attendance.

Lorelai finds out about it at one of her weekly dinners with them as Emily spends the meal mocking Jason’s date, unknowingly making Lorelai feel insecure and defensive. When she confronts him about it, he explains that she put him in that position and that it was actually torture to spend time with this woman that he calls his friend. But as much of a red flag that is for me personally, it’s exactly what Lorelai needs to hear to feel secure in their relationship. 

In the end, their values end up diverging when it comes to family. While Jason comes from a family that ruthlessly uses business to hurt and retaliate against each other, Lorelai still believes in family coming first, a sentiment shared by her own mother. Which is why Lorelai ends her relationship with Jason after he decides to sue her father for a business betrayal and Emily (temporarily) leaves Richard for doing the betraying and hurting their relationship with Lorelai. 

Jason could’ve been the one to give Lorelai both the life she wanted and the life her parents wanted for her, but it’s her loyalty to her family that drives them apart.

So yeah, even Luke’s basicness seems particularly attractive after all of that. Which is basically why Nice Guys like Luke need the jerks like Christopher and Jason to exist to make him seem all the better.