‘Gilmore Girls’: Did Richard Gilmore Cheat on Emily Gilmore With Pennilyn Lott?

Cheating, or behavior that could be considered cheating, was a pretty common theme in Gilmore Girls. Rory Gilmore cheated on Dean Forrester and Logan Huntzberger. Lorelai Gilmore slept with Christopher Hayden hours after ending her engagement to Luke Danes, and Paris Geller cheated on Jamie with her professor, Asher Flemming. Not all of the cheating in Gilmore Girls was so obvious, though. Some people consider Richard Gilmore and Pennilyn Lott’s clandestine lunches cheating. Others do not. So, did Richard cheat on Emily with Pennilyn? Scott Patterson thinks so, but some fans do not. 

Scott Patterson thinks Richard Gilmore had an emotional affair 

In season 4 of Gilmore Girls, Richard and Emily run into Richard’s ex-fiancee, Pennilyn Lott, at a Yale football game. Lorelai Gilmore’s presence at the game indirectly led to the revelation that Richard had been meeting with Pennilyn at least once a year for the entirety of his marriage to Emily. It was a shocking moment, but did Richard Cheat? 

Patterson had a hot take on the Richard Gilmore and Pennilyn Lott storyline that played out during a small part of season 4 of Gilmore Girls. In his podcast, I Am All In, Patterson posited that Richard Gilmore and Pennilyn Lott had an emotional affair. Linda Gehringer, the actor who played Pennilyn for a single episode, was less committal about whether her character’s lunch dates with Richard constituted an affair. 

‘Gilmore Girls’ fans don’t think Richard Gilmore and Pennilyn Lott’s lunches constitute cheating 

While Patterson’s take is pretty clear, fans of the famed series don’t think Richard’s actions are nearly as cut and dry. Reddit fans discussed the Richard Gilmore and Pennilyn Lott storyline, and most agree that while Richard acted dishonestly, he wasn’t exactly cheating on his wife. 

Fans of the series concede that the Richard Gilmore and Pennilyn Lott storyline was ambiguous, but since the former flames only had lunch once a year, it wasn’t cheating. Had they met monthly or even a few times a year, one could classify it as an emotional affair. Since their meetups were just a once-per-year event, the connection likely wasn’t too deep. 

That doesn’t mean Richard was in the right, though. Regardless of how often Richard and Pennilyn met, he should have told his wife. The fact that he felt the need to keep it a secret indicates there was more to the decision than an innocent desire to stay in touch. The clandestine nature of the meetups makes it all very suspect. 

We think Richard’s behavior was inappropriate, and the secrecy was certainly a betrayal. It’s hard to call what he did cheating, though, since we don’t have all the facts. From what we know, we are inclined to say he didn’t cheat, but we think he had unresolved issues around the end of his romantic relationship with Pennilyn. That is problematic in a completely different way. 

Amy Sherman-Palladino missed a golden opportunity to expand the storyline 

Gilmore Girls creator Amy Sherman-Palladino inexplicably dropped the Richard Gilmore and Pennilyn Lott storyline after season 4. While Emily and Richard did split briefly, Pennilyn was not mentioned as a major factor in their marital strife. That might have been a mistake. The lunch dates were so troubling to Emily in the moment that it felt awfully strange that it was never mentioned again. 

Patterson and Linda Gehringer agree. During their chat on Patterson’s podcast, both noted that they thought Sherman-Palladino would stretch the storyline much longer than she did. In fact, they mentioned that Ed Herrmann, the actor who portrayed Richard Gilmore, thought there would be more to the story than there inevitably was. Pennilyn Lott was not mentioned in the Netflix revival, Gilmore Girls: A Year in the Life, either. Much of the revival centered around the ladies of the Gilmore family dealing with Richard Gilmore’s death.