‘Gilmore Girls’: Fans Discover a Plot Hole Regarding the Dragonfly Inn

Most long-running shows have a few plot holes. Usually, fans can overlook them. Financial plot holes, in specific, are exceedingly common, but Gilmore Girls fans can’t let go of one glaring financial plot hole in the show’s seven-season run. How did Lorelai Gilmore open the Dragonfly Inn if she used her investment money from Richard Gilmore to pay for Rory’s Chilton tuition?

Lorelai Gilmore used the money from her father’s investment to buy the Dragonfly Inn

In Season 3, Lorelai and Sookie St. James decide to open an inn together. The best friends had been dreaming of the possibility for years and finally had the perfect property picked out. The well-time maturation of an investment made for Lorelai by Richard helped the plan along. Before putting in an offer on the property, Richard presented Lorelai with a check for $75,000, which she intended to use on the inn.

Michel Gerard sitting in the dining room of The Dragonfly Inn
Michel Gerard in ‘Gilmore Girls: A Year in the Life’ | Netflix

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Later, it was suggested that she did, in fact, use the money to purchase the property. There is a big problem with the storyline, though. Lorelai had seemingly already used that money for a different cause. Did she have multiple checks for $75,000, or did the writers forget that she already used the cash to start a fight with Emily Gilmore?

Earlier, Lorelai supposedly used that money to pay Richard and Emily back for Rory’s Chilton tuition

Rory’s decision to go to Richard and Emily for help with Yale was made behind Lorelai’s back, but she had a good reason. Rory didn’t want Lorelai to spend the money from her investment on Yale instead of the Dragonfly. With financing for Yale secured, Rory told Lorelai she could use the money to purchase the inn with Sookie.

Reddit users see one big problem, though. Lorelai shouldn’t have had much money left to invest in the Inn or to pay for Yale, for that matter. When she was speaking to the Bursar’s office at Yale, she noted that she no longer had the $75,000 that prevented Rory from getting financial aid. She insisted she had already used the money. So, which was it? Did she earmark the funds for her business venture, or did she use the money to pay back Richard and Emily? It seems like a plot hole that was never fully explained.

How much would Chilton have cost?

So, if Lorelai used Richard’s investment money to pay the couple back for Chilton, she likely wouldn’t have had enough money to buy the Dragonfly Inn. Some fans argue that she would have had money left over from the investment, even after paying for Chilton, which could have served as her down payment for the inn. Still, it hardly seems like the money would be enough to repay Richard and Emily and buy a property.

Alexis Bledel as Rory Gilmore and Lauren Graham as Lorelai Gilmore in 'Gilmore Girls'
Alexis Bledel as Rory Gilmore and Lauren Graham as Lorelai Gilmore in ‘Gilmore Girls’ | Warner Bros./Delivered by Online USA

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Rory started prep school as a sophomore in 2000 and graduated in 2003. That means Richard and Emily would have needed to foot the bill for three full years of school. Chilton wasn’t just an imaginary school, though. The elite prep school was based on Choate Rosemary Hall. Since Chilton was based on a real school, we can assume the tuition was about the same.

According to Niche, the Wallingford, CT school charges $45,000 a year for non-boarding students for the current school year. Even 20 years ago, the tuition likely ran upwards of $20,000 per year. If Chilton cost $20,000 per year, Lorelai would have owed Richard and Emily $60,000 by the time Rory graduated. If that was the case, she would have had $15,000 left from her investment check after paying Richard and Emily. That hardly seems like enough to buy a property like the Dragonfly, no matter how dilapidated it was.