Gilmore Girls: 10 Times Viewers Felt Bad For Jason

Jason Stiles (aka Digger) was introduced in the fourth season of Gilmore Girls as an old family friend and Richard’s future business partner. Personality-wise, he was the male version of Lorelai. Aside from Christopher, he was one of the few men who could keep up with Lorelai. The two made a fantastic couple when they finally acted on their attraction, but as is the case with many of Lorelai’s suitors, it didn’t last.

As confident and charismatic as Jason was, he was burned badly by not only the Gilmores but also by his own family. He gained nothing from working with Richard, his father, or from dating Lorelai. In fact, his life got worse when he entertained a relationship with the Gilmore clan.

10 Emily & Richard Judged Him Harshly

Due to Richard’s intense relationship with Jason’s dad, he wasn’t particularly thrilled when Jason reached out to him. Even Emily was against Jason, but she encouraged Richard to take his call because she was curious about what he had to say.

And while the Gilmores took a chance on Jason eventually, they were never completely #TeamDigger. It seemed like Jason was always trying to prove his worth to the Gilmore clan – just as Lorelai did.

9 Richard Screwed Him Over… Hard

Jason went out of his way to go against his own father and business to join forces with the powerful Richard Gilmore. He bought his way into the company and brought a percentage of his clients with him. Richard and Jason made a great team until Jason’s dad decided to sue Jason and Richard.

When Richard realized he was about to lose his financial stability and reputation, he went against Jason and made a deal with his father instead. So, not only did Jason lose his business, he lost his partner and his dad at the same time.

8 Jason Had No Choice But To Sue Richard

Lorelai was shocked when she heard that Jason was counter suing her dad. She couldn’t be with someone who was in an ongoing lawsuit with her family.

Friday night dinners would be more intolerable than they already were. In the span of a couple of days, Jason lost everything he cared about. If he didn’t sue Richard, he would have to move to a different state and start from scratch.

7 The Gilmores Didn’t Want The Two Of Them Together

When Jason and Lorelai were dating on the down-low, they pretended to be friends when they were around Richard and Emily. At one event, Lorelai and Jason even had to pretend to be each other’s dates because they showed up (purposely) alone.

Emily didn’t want the two of them looking like outcasts, so she matched them as dates for the day. Later, when Lorelai brought up the idea of dating Jason, Emily literally laughed in her face and found the idea ridiculous.

6 Lorelai Wanted Their Relationship Kept a Secret

Jason knew that dating Lorelai could be risky because of his working relationship with Richard, but he was willing to take a chance. He and Lorelai had known each other for years and fit nicely into each other’s lives.

But just because they were getting along didn’t mean that Lorelai was ready to let the cat out of the bag. Because of her parents’ reactions to everyone she dates, she wasn’t ready to tell them that she and Jason were dating. This upset Jason, but he ultimately understood. However, being kept a secret could not have been easy for him.

5 Lorelai Should Have Gone Easier On Him During Their Break Up

When Lorelai realized that Jason was serious about suing her dad, she knew she wouldn’t be able to date someone who was in a lawsuit with her parents. Even though they liked each other and Jason gave Lorelai a key to his house, Lorelai dumped him in a public place without much emotion.

Basically, she kicked him when he was down and didn’t care about how he felt. She didn’t want to be between her boyfriend and her dad, but poor Jason just lost a great many things, and she could have been more sensitive to his perspective.

4 She Was Also Cold To Him At The Dragonfly’s Soft Launch

On the opening night of the Dragonfly Inn, Lorelai was a nervous wreck. She wanted the evening to go well and hoped everyone in the town would say good things about the business she, Sookie, and Michel built together. Surprisingly, as Lorelai was dealing with customers, Jason arrived.

Jason wasn’t invited and didn’t have a room to sleep in, but he didn’t care. He wanted to win Lorelai back and was willing to wait at the Dragonfly for her to talk to him. But with Lorelai’s peaking interest in Luke, her mind and her heart were already elsewhere. Jason got the boot and wasn’t seen again in the original series.

3 His Relationship With His Parents Was Disheartening

Not much is known about Jason’s personal relationship with his parents, Floyd and Carole, but it’s safe to assume they were similar to Richard and Emily. Richard and Floyd had worked together for decades, and Emily and Carole appeared incredibly close when they had dinner at the Gilmores.

And after hearing Jason’s pitch to Richard, it’s safe to assume that he has an awful relationship with his dad since he was trying to take down his business. Without Lorelai and his parents, Jason appeared to be a loner.

2 Lorelai Got Mad At Him For Bringing A Date To A Work Function

The moment Lorelai got mad at Jason for bringing a date to a work function was the moment fans realized she was being a hypocrite. She didn’t want people knowing that she and Jason were dating, and she didn’t want to be his date at functions for the same reason.

She had no right to be mad at Jason for bringing a friend as a date to save face when she denied him every chance to whisk her away as his date. Jason felt awful for simply following the rules that Lorelai set in place.

1 His First Date With Lorelai Was Ruined

Lorelai initially turned Jason down when he asked her out. She thought it would be too weird since he was going into business with her dad. But when her mom and dad annoyed her at the Harvard vs. Yale football game, she decided to go on a date with Jason to spite them. Jason took her to a very expensive restaurant that everyone was raving about, but Lorelai’s need to be in the center of the room ruined the evening.

She felt a private dining room was awkward, so the two left the dinner early. Afterward, they drove around until they found what they wanted to do. In retrospect, Jason created a beautiful night for Lorelai, and she ruined it because of a nice gesture.

About The Author

Lynn Gibbs
(1645 Articles Published)

Lynn is a nomad who travels the globe on the hunt for her next adventure with her husband. A lover of being outside (and finding the best latte in town), Lynn is typically hiking, walking, or jogging when she’s not focusing on her love of writing. When it comes to shows streaming on Netflix or anything Bravo-related, Lynn’s your gal.

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