Although Emily and Richard's Gilmore Girls cast of characters were fiends for drama, but few of them would it this. Luke appeared to be a straight-talking, no-nonsense small-town guy, but this personality didn’t stop him from hiding a secret child from his fiancée for months. Similarly, Emily and Richard appear to disapprove of Lorelai and Rory’s chaotic personal lives, but a look at their relationship proves the apple landed near the tree.

Two Of Gilmore Girls' Most Unloved Stories Were Virtually Identical
April Nardini's arrival and Rory's relationship with Marty and Lucy both arrived around the same time and highlighted the same Gilmore Girls problem.
While season 4 includes some of Jason’s Gilmore Girls exit is one of the conduits for this big breakup, there is a more complex storyline going on underneath the surface. Emily and Richard’s breakup makes more sense on a re-watch as it becomes clear that the show was setting it up all along.
Gilmore Girls Was Quietly Setting Up Emily & Richard's Separation Throughout Season 4
Richard and Emily’s Breakup Was Foreshadowed In Earlier Episodes
Although Richard backstabbing Jason by making a deal with his father is seemingly the straw that broke the camel’s back, Emily and Richard’s breakup is caused by various events dotted throughout Gilmore Girls season 4. Firstly, the fact that Richard is still even working in season 4 is a major red flag. He promised Emily that he would retire so that they could spend more time together and briefly fulfilled this promise, although season 2, episode 12, “Richard in Stars Hollow,” proved that Emily didn’t always want him around either. Nevertheless, the stress of continuing to work adversely impacted their relationship.
The revelation that Richard had secretly been going to lunch with his former fiancée, Pennilyn Lott, for years without ever telling Emily dealt their relationship a major blow.
Not only did Richard refuse to retire, but he also gambled his and Emily’s pension on the risky venture that led to Jason suing him. Add in the fact that Richard didn’t appreciate all that Emily did for him, alongside missing her friend’s funeral for work, and it is clear that the pair weren’t working together. The revelation that Richard had secretly been going to lunch with his former fiancée, Pennilyn Lott, for years without ever telling Emily dealt their relationship a major blow. After that, Richard inadvertently causing Jason and Lorelei’s breakup by reneging on his deal with Jason didn’t help.
Richard & Jason's Lawsuit Was The Final Nail In Richard & Emily's Marriage
Richard Jeopardised His Relationship With Emily, Lorelai, and Rory Over Business
One harsh reality of Lorelai’s Gilmore Girls character arc was that she didn’t always have Rory’s best interests at heart, especially when it came to interactions with her parents. Lorelai was often so busy feuding with Emily and Richard that she ignored reality, arguing that Rory should only have applied to Harvard instead of listing Yale as a safety school solely because Lorelai’s parents approved of Yale. It is clear where Lorelai gained this trait when viewers look at Richard’s bullish behavior throughout season 4. Richard shamelessly double-crossed Jason during their business dealings and jeopardized Lorelai’s relationship in the process.
In doing so, Richard risked everything that he and Emily had worked for with Lorelai, Rory, and their shared Gilmore family dinners. Richard got lucky when Lorelai sided with her father and dumped Jason, but she would have been equally justified in siding with her romantic partner given Richard’s underhanded maneuverings. Interestingly, Gilmore Girls season 4 implies that Richard doesn’t consider anything about his conduct unethical, and he is only annoyed that Jason’s relationship with Lorelai impacted his personal life. Viewers can surmise that Richard always conducted business like this, so the break-up is arguably karmic justice for him.
Richard & Emily's Separation Was Actually Good For Gilmore Girls
Emily and Richard’s Separate Lives Were More Complex Than Expected
Since Rory and Lorelai always received the lion’s share of the show’s screen time, Gilmore Girls frequently sidelined Emily and Richard in early seasons. As such, the pair’s breakup was arguably a good thing as it allowed the show to explore them more as individual characters and not a unit. As Rory and Logan’s Gilmore Girls story began in season 5, viewers got a new level of insight into the couple that raised Lorelai. This led to some funny moments, but also sad ones. Emily crying alone after her date was devastating, but this scene also humanized a seemingly cold character.
By the time one of the best Gilmore Girls Christmas episodes reunites Emily and Richard, viewers have seen a new side of them.
Similarly, Richard’s new hobbies and his attempts to golf with Luke were endearing after years of Gilmore Girls treating the character as either a benevolent patriarch or a stern, self-serious businessman. It is endearing to see Richard struggle when earlier seasons portrayed him as a stoic figure, and humanizing to watch the self-righteous workaholic reckon with the realization that all his years of making money were as much for his own ego as his wife and family. By the time one of the best Gilmore Girls Christmas episodes reunites Emily and Richard, viewers have seen a new side of them.
Gilmore Girls Needed Emily & Richard To Get Back Together
Richard and Emily Belonged Together And Their Separation Proved This
While Richard and Emily’s separation was good for their character development, Gilmore Girls still eventually needed to reunite the couple. Often, Gilmore Girls is listed among classic cozy comfort watches, and the show is ittedly low on high-stakes, potentially traumatizing drama. However, the series isn’t short on conflict, and Richard and Emily’s breakup lasted longer than viewers might have anticipated. It wasn’t just the need for a happy status quo that brought the duo back together, but the fact that Gilmore Girls required them to be a unit for future storylines. Lorelai’s relationship with Luke and Rory’s Logan romance justified this.
Soon, Gilmore Girls needed Richard and Emily to be the strong foundation of the eponymous family again.
Early in season 5, it made sense for Emily and Richard to remain separated. Lorelai and Rory were in an atypically stable place after the Dean debacle and both were pursuing relationships that lasted until the series finale. In the wake of Jess’ Gilmore Girls exit, things seemed comparatively stable. However, as Mitchum Huntzberger and April Nardini entered the picture, Lorelai and Rory’s lives became more complicated. Soon, Gilmore Girls needed Richard and Emily to be the strong foundation of the eponymous family again. Thus, their breakup needed to be resolved now that Gilmore Girls had made the two pivotal characters more believable and rounded.
Gilmore Girls and A Year in the Life are available to stream on Netflix.

Gilmore Girls
- Release Date
- 2000 - 2007-00-00
- Network
- The WB
- Cast
- Jared Padalecki, Milo Ventimiglia
- Seasons
- 7
- Streaming Service(s)
- Netflix