'Gilmore Girls': 3 of Lorelai Gilmore's Most Heartbreaking Moments With Her Father, Richard Gilmore

Lorelai Gilmore (Lauren Graham) had a strained relationship with her bow-tie-wearing father on Gilmore Girls. Crushed when Lorelai dropped out of high school after getting pregnant with Rory Gilmore (Alexis Bledel), Richard Gilmore (Edward Herrmann) had to face the fact that his daughter’s life didn’t turn out how he imagined. 

Lorelai eventually moved out of her parents’ house to raise Rory on her own. She settled in the fictional town of Stars Hollow. Only years later, and at her mother’s insistence, did she show up for weekly dinners. Through the years, Lorelai and Richard had heartwarming moments but they had their fair share of heartbreaking scenes too. 

When Richard Gilmore explains why he yelled at Straub Hayden

Originally airing on March 1, 2001, Gilmore Girls Season 1 Episode 15: “Christopher Returns” marked the introduction of Rory’s father, Christopher Hayden (David Sutcliffe). He made a surprise visit to Stars Hollow at the end of the previous episode. Until then, he’d only been mentioned by name. 

Christopher joined Rory and Lorelai for dinner at the Gilmore house with his own parents, Straub (Peter Michael Goetz) and Francine Hayden (Cristine Rose). Dinner hadn’t even been served and an argument had broken out. Richard defended Lorelai — or so she thought — before retreating to his study.

Lorelai thanked her dad for sticking up for her, thinking he did it out of protectiveness for her. But Richard told her he only did it because the family name was being attacked. 

When Lorelai Gilmore spends the day with her father

Rory and Lorelai got a visit from Richard in Gilmore Girls Season 2. After retiring from the insurance business, Richard spent a little too much time at home for Emily Gilmore’s (Kelly Bishop) liking. In need of a break, she sent Richard to Stars Hollow to spend the day with Lorelai and Rory. 

Panicked about spending the entire day with her father, Lorelai counted down the hours until Rory got home from school. In that time she had an awkward conversation about grapefruit and another about the clothes she wore to work.

Everything came to a head after Richard insisted Rory couldn’t accept a car as a gift from her then-boyfriend, Dean Forester (Jared Padalecki). Instead of being a fun episode about spending the day together, it only highlighted the sad state of Lorelai and Richard’s relationship.

When Richard Gilmore’s hospitalized

After getting uninvited to her parents’ annual Christmas party, Lorelai is shocked to learn her father’s been rushed to the hospital. In Gilmore Girls Season 1 Episode 10: “Forgiveness and Stuff,” Lorelai is panicked, thinking her father’s going to die. 

On the way to the hospital with Luke Danes (Scott Patterson), Lorelai talked about being a disappointment to her father. When she finally gets there, she can’t bring herself to see Richard. She finds every reason to avoid entering his room until Luke eventually calls her out on it. 

Eventually, Lorelai steps into his room. She and her father make eye contact, and just as she’s about to say something, Rory and Emily come in. Realizing her father’s going to be OK she cries to Luke. It’s a heartbreaking moment showing that despite the state of their relationship, Lorelai truly cares for her father. 

Watch Gilmore Girls and Gilmore Girls: A Year in the Life on Netflix.

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