The Best and Worst Moments of Every Gilmore Guy

The Best and Worst Moments of Every Gilmore Guy

Welcome to MsMojo. We love our Gilmore Girls around here, and we love the guys who love them too. Sometimes, anyway. But when they’re wrong, we’re not afraid to say so. Today we’ll be looking at the best and worst relationship moments from the most significant men in the “Gilmore Girls” world. We won’t be including wannabe boyfriends, brief flings, or anyone who rates as almost perfect. Like Dave Rygalski.

Zack Van Gerbig
Worst: Sinking Hep Alien’s Big Chance

After years of grinding away in local gigs, it looks like Hep Alien’s ship is finally coming in when they get the chance to play for a label rep. Unfortunately, this coincides with Zack’s sudden insecurity about Brian and Lane’s friendship. Never mind that Lane has never given Zack any reason to doubt her. Maybe he just realizes what the audience has known all along: That she’s too good for him, and this relationship never really made sense. He shows up on the pivotal night with a major attitude, and proceeds to derail the performance with his antics, culminating in a physical fight. Worse, he remains unapologetic despite how heartbroken Lane is by their ruined opportunity. It should have spelled the end of Zack and Lane’s relationship.

Zack Van Gerbig
Best: Proving His Love Through Song

When Lane inexplicably accepts Zack’s sudden marriage proposal, there’s only one obstacle left. Mrs. Kim. And her condition for agreeing to the union takes Zack by surprise. After 20 hours of non-stop work, Zack still hasn’t been able to crack the elusive code on a hit song. However, when he proves willing to take Mrs. Kim’s collaborative advice, he finally has a breakthrough. This was a big turning point for Zack’s character, showing him willing to be flexible and put his pride to the side for Lane’s sake. And winning Mrs. Kim’s approval is nothing to scoff at either. Though, let’s be clear, it’s still not quite on the level of reading the whole Bible in one night.

Jason Stiles
Worst: Crashing the Dragonfly Opening

We’ll start by throwing Jason a bone. His decision to sue Richard Gilmore was justified. But something like that does tend to put a strain on a relationship, and we can’t fault Lorelai for ending things between them either. Apparently Jason doesn’t see things our way though. His disregard for the facts of the situation, that’s not great. But the bigger problem is how Jason refuses to respect Lorelai’s boundaries. Ambushing her at her place of work, especially during what he knows is a stressful weekend for her is overbearing and inconsiderate no matter how you spin it. It looks even worse when you consider how Lorelai, who tends to be a bit rigid, learned to be accommodating of Jason’s needs throughout their relationship.

Jason Stiles
Best: First Date

Then again, maybe the last scene between Lorelai and Jason was inevitable considering how tireless he was in getting her to date him in the first place. Even then Lorelai was not impressed with his idea of a good time. Trying to salvage the evening, Jason agrees to leave, and takes Lorelai for her favorite fast food instead. Except she refuses to eat when he declines to order any for himself. Finally, they wind up at a grocery store out of sheer desperation, where Jason proves he really will do anything to make Lorelai happy. Their mismatches in taste indicate this relationship is not destined to last, but Jason’s dogged efforts to give her a nice date are very endearing. As is the makeshift dinner they scrounge up together.

Dean Forester
Worst: Cheating With Rory

From his increasingly pronounced jealous streak to his habit of dumping Rory publicly, Dean has a few low points to contend with. But nothing beats this one for recklessness or collateral damage. As Rory struggled to adjust to college and Dean found his hasty marriage to Lindsay to be increasingly unsatisfying, the two exes were slowly drawn back together over the course of season four. By the time they’re alone in Rory’s bedroom it’s like watching a slow motion train crash as we witness them both dismiss his relationship and give in to their worst impulses. Rory would go on to try and justify this behavior. But even though Dean eventually comes to his senses, there’s no excusing his actions here.

Dean Forester
Best: Being the Perfect Date

Back in a simpler time, Dean is just the cute boy from the market, and Rory is just the teenage girl nervous about asking him to her school dance. The worry is for nothing though. The Chilton Formal isn’t his scene, but he is seemingly happy just to be spending the evening with his new girlfriend. From banishing the mean girls to sweet slow dancing, Dean is dream date material throughout the episode. He won’t even let Tristan spoil the night, holding his ground while refusing to be goaded into a fight. We know that puppy love isn’t enough to go the distance for these two, but in those early days, Dean gave us a moment right out of our teenage dreams.

Jackson Belleville
Worst: Lying About His Vasectomy

With the season five birth of their second child, Sookie and Jackson have completed the all-American family. And Sookie, for one, wants to make absolutely certain that they remain a quartet. Now, she definitely should have discussed this with Jackson rather than springing it on him. But we cannot justify the way he responded. Sookie’s inevitable pregnancy finally forces Jackson to confess that he never got the procedure. Which she takes about as well as one might expect. To be clear, this entire issue deserved a calm, mature discussion between both parties. But Jackson keeping a secret that had huge implications for their family, and for Sookie’s health definitely makes him come off the worse of the two.

Jackson Belleville
Best: The Basket Buyout

Okay, on closer inspection, Jackson and Sookie may have always had some communication issues. Like when Jackson didn’t know how to ask Sookie to move in with him, and Sookie didn’t realize he wanted her to. Thinking she wasn’t serious about him, Jackson refuses to bid at the town basket auction, letting Sookie’s lunch date go to Kirk instead. However, once they finally talk honestly about their insecurities, it’s clear how much in love they really are. Of course, Jackson still has to go through Kirk to get the basket back. But the whole chain of events helps him figure out what he really wants. And proves that Jackson can make himself clear in pretty adorable fashion.

Max Medina
Worst: Proposing as a Power Play

What’s a good indication that a couple should have stayed broken up? Maybe if they can’t even get out of the house for their second first date without tension breaking out. Max instantly turns possessive after encountering Luke at the Gilmore House. He makes incorrect assumptions about his relationship to Lorelai, before throwing his own interim dating experiences in her face to make her jealous. Lorelai at least sees the writing on the wall. But in response to her suggestion that they break up again, Max takes an unhinged left turn. Nothing about this feels organic or in good faith; more like a transparent attempt to mark his territory. Lorelai calls it for what it is, but however Max denies it, it still feels manipulative.

Max Medina
Best: Cafe Banter

Max and Loreali’s courtship started with the lure of forbidden fruit. His role as Rory’s literature teacher instantly complicates any potential attraction, but while that initially gives Lorelai pause, he proves to be persuasive enough to get her to consider him. Okay, maybe not. At first it looks like Lorelai will handily lap Max in a battle of wits. Except he proves to be a surprisingly quick study. Whether he’s right or whether Lorelai simply recognizes a worthy opponent, she agrees to go on a date, and their relationship blossoms afterwards. True, it ends badly not once, but twice, and it’s rife with issues, but chemistry was never one of them. We can appreciate that in different circumstances, Max might have been a perfect partner to the formidable Lorelai Gilmore.

Richard Gilmore
Worst: Leaving Emily Out of the Loop

At their best, Emily and Richard Gilmore are a perfectly matched team. But whether it's a generational shortcoming, or plain old hubris, Richard also has an unfortunate tendency of keeping Emily in the dark about certain matters. His early retirement represents a consequential shift in their lives, which he neglected to prepare her for. However, a worse breach of trust comes when Emily discovers that Richard has continued to see his college sweetheart on a yearly basis for decades. Incidents like these stack up across the first half of the show, with a noticeable effect on Emily’s mental state over time. Feeling increasingly undervalued, she eventually reaches a breaking point that leads to a dramatic separation between the pair.

Richard Gilmore
Best: “My Name is Bill”

Whatever faults he has, Richard is not stupid. It doesn’t take long before he realizes the error of his ways, and the Gilmores reunite, marking the occasion with a lavish vow renewal. Here, Richard proves he really has learned when he chooses an obscure favorite song of Emily’s from decades ago as their first dance. Considering how invisible Emily was feeling prior to the separation, this song is indeed the perfect note for their next chapter. It proves that Richard is willing to notice and celebrate the details important to his partner. We never really had any doubt about the depth of the love between these two, of course. Season one laid the groundwork with an emotional promise from Richard to Emily that still gets us every time.

Jess Mariano
Worst: The House Party

From the beginning Jess had issues with boundaries, often making Rory downright uncomfortable in his pursuit of her. Even once they were officially a couple, his mercurial temperament keeps her consistently off balance. Upset about having to repeat his senior year, and unwilling as ever to communicate, Jess retreats from the party to brood in private. When Rory follows to comfort him, he pushes to take things further, ignoring her repeated protestations. This isn’t just a low point for Jess, but arguably the worst moment for any guy on the series. And made even more appalling by the fact that he lashes out and blames Rory. He immediately regrets his actions, but this is the kind of thing we find hard to forgive, and will certainly never forget.

Jess Mariano
Best: A Push in the Right Direction

One thing we can say for Jess is that he was always supportive of Rory’s Ivy League goals. And unlike Dean he never saw them as prohibitive to their relationship. He did, of course, beg her to drop out of college a year later to run away with him. But in the long term, Jess realized Rory was right to say no. Which is why he reacted so strongly to discovering later that she had left school all the same. Rory was slowly realizing this mistake on her own, but Jess’ outburst gave her the last push she needed to get her life back on track. As problematic as he could be, Jess’ honesty in this moment reveals a genuine concern for Rory and her future that was undeniably impactful.

Christopher Hayden
Worst: Interrupting Friday Night Dinner

Just when it looked like Christopher and Lorelai were finally ready to be together, he found out his girlfriend was pregnant. It’s a devastating blow for them, but they both accept there’s no way to move forward as a couple. Or so we thought, anyway. Christopher’s desperate attempt to force a conversation with Lorelai is the ultimate selfish act. He is deep in his feelings, and he decides to make that everyone’s problem. Looking for pity and comfort, Chris never stopped to consider how his actions might impact the women around him. He uses love as an excuse to make this awful situation entirely about himself, displaying cringeworthy disrespect for Sherri, and a callous disregard for the feelings of either Rory or Lorelai.

Christopher Hayden
Best: Finally in Paris

As teenagers, Lorelai and Christopher talked about traveling in Europe together after high school. And though life intervened, they did eventually make it to Paris. The trip gets off to a bumpy start when jet lag causes them to miss their dinner reservation, and they’re forced to wander the streets trying to find food. Luckily, Christopher remembers he can use his recent inheritance to grease some wheels. Throughout the episode we see why Lorelai and Chris are so good together. Their banter is unmatched, and their long history gives them an understanding of one another that is rare. This gesture doesn’t feel like a stunt, but a heartfelt attempt to realize an old dream. Chris carried a torch for Lorelai for a long time, and his sincere devotion on display here is touching.

Logan Huntzberger
Worst: An Aggressive Third Wheel

Few people would take it well if they found their significant other meeting up with an ex behind their backs, so we can understand Logan’s sour feelings. But that doesn’t make the way he handled the encounter with Rory and Jess any better. Forcing himself in on their reunion, Logan is completely insufferable, dangling his wealth and privilege in a way that just feels gross. He makes his intent to insult even more blatant when he starts challenging Jess’ intellect. We’ll give Jess credit and say it shows a lot of growth that he didn’t take the bait here. But of all the sides Logan showed during his time on the series, this is by far his least attractive.

Logan Huntzberger
Best: Saving the Paper

Logan first got us swooning with his literal call to adventure in the iconic “You Jump, I Jump, Jack.” But arguably his finest moment comes when he finds the Yale Daily News in crisis following Paris’ meltdown. With the paper’s integrity on the line, he swings into action to help Rory, offering a sharp skill set, fresh material, and valuable management suggestions. And when it looks like all the staff’s hard work might be in vain, he buys them time to get to the finish line. Not only does this show us how much Logan has been holding back behind his slacker facade, it proves that he and Rory are more than a good couple: They’re a true partnership. They support and complement each other perfectly, and together there’s nothing they can’t do.

Luke Danes
Worst: Keeping April From Lorelai

Discovering you have a twelve year old kid? Yeah, that would rock anyone’s world. But Luke has never been great with change to begin with, and as he struggles to adapt he puts a firm separation between his daughter, April, and the rest of his life. But when Lorelai meets April at the diner, worlds collide. Lorelai is remarkably understanding, all things considered. However, Luke doubles down on his poor handling of the situation when he reiterates his intention to keep her out of April’s orbit. It’s clear Luke is overwhelmed. But rather than let his partner help him manage those feelings, he makes unilateral decisions that lock her out of the equation entirely. And when he asks to postpone their wedding it causes Lorelai to doubt their entire relationship.

Luke Danes
Best: The Going Away Party

Luke fell for Lorelai at first sight, but what ultimately made him endgame was how much he loved Rory as well. With the clock rapidly ticking down on her last days in Stars Hollow, this man who hated every event the town ever hosted went into overdrive to throw her an epic going away party. Luke oversees every step of the planning and execution while also managing to keep the party a secret from the Gilmore Girls. And when rain threatens to thwart their efforts, he’s ready with a Plan B. While he’s not always great at expressing himself, Luke is at his best when he can show his love. The party was the grandest of grand gestures, allowing him to declare his true feelings for Lorelai in terms far deeper than any words.

Which Gilmore Guy moment makes you swoon? Which makes you rage? Pour yourself some coffee and tell us about it in the comments.