Outside of the relationship between Lorelai and Rory Gilmore, work and career paths were the driving force behind many of the characters. Richard Gilmore based his life on his business, Lorelai and Sookie always dreamed of owning their own inn, Luke took pride in his diner, and Rory spent the entire series gearing up to become a journalist. The people of Stars Hollow are hard workers.
With hard work comes risks and tough choices. Along the way, every business owner or coworker is faced with a decision that could define their entire business or career path. And while every character on Gilmore Girls should be commended for their efforts, not every decision paid off.
When Lorelai and Sookie were renovating the Dragonfly Inn and gearing up for opening day, the construction team reminded Lorelai that while they adored her, they were basically working for free. They ran out of money and needed more to finish the job.
This is something that Lorelai hid from Sookie and didn’t want to face until it was too late. While she loathed going to her parents, as a business owner she needed to tackle this head-on and be honest with her business partner. She eventually got the money through a loan from Luke.
Everyone loves a grumpy Luke; it’s part of his shtick. However, there comes a time as a business owner where his personal preferences should be left out of everyday business operations. As a man who wanted his diner to do well, he loathed when the place was full. What’s worse for Luke was when people stayed for extended periods of time.
Whether they were enjoying conversations or staying for a business lunch with electronics, Luke hated it. There has to come a time where people will stop going to Luke’s because the owner is a stick-in-the-mud curmudgeon, yelling at customers for enjoying their time and spending their money there.
After a few chaotic weeks at the Dragonfly Inn, Lorelai decided to get her hair done and Sookie would stay at the inn for a kitchen delivery. But as Lorelai’s hair was being worked on, she got a phone call saying no one was there to accept the delivery. When Lorelai finally got in touch with Sookie about missing the delivery, Sookie’s excuse was that she had a kid. Sookie had to have known that being a working mom was going to have its challenges, but she should have kept open communication with Lorelai. That was a hurtful moment in their partnership.