- “When it's right, it's right, and me and Lorelai are right”
- —Jason to Luke[src]
Jason and Lorelai knew each other as teenagers in camp, where she had the nickname umalauts and she called him digger. They parted ways until they were reunited by Jason and Richard Gilmore's choice to become business partners.
They started a secret relationship for five months, until Floyd Stiles revealed the relationship. They eventually broke up when Jason sued Richard for leaving their partnership and Lorelai sided with her father.
Richard and Emily Gilmore had planned a launch party in celebration of his partnership with Jason. Lorelai and her friend Sookie St. James would be catering for them. When they told Jason, he told them he thought a catering party would be the wrong way to go. Emily was upset which made Lorelai confront him. Jason invited Lorelai for dinner but she declined.
After a blow up with Emily at the Harvard-Yale game, she phoned Jason and accepted his invitation for dinner. They go out to a fancy restaurant but Lorelai felt uncomfortable when Jason placed their table in a separate room from the main dining area.
They decided to go a supermarket to shop for food instead. When they brought the food, they ate outside. Lorelai asked Jason to keep the relationship from her parents.
Lorelai was surprised when Jason showed up at her parents house to give them something in the middle of their Friday night dinner. They pretended they hadhave only just met since they were at camp. Lorelai asked Emily to give Jason some marzipan as a joke, and she laughed when Jason realised how horrible it is.
Lorelai then left the room to phone Jason, who was in his car outside. She was happy he had returned from Australia and he said he thought about her a lot and invited her out for dinner on Monday.
Jason made Lorelai breakfast the next morning, which she thought was lovely. Lorelai wondered what they would say to people about them. Jason said they should say something simple but Lorelai says nothing is simple for her parents. Lorelai says maybe they shouldn't tell them, but Jason says secrets have a way of being found.
At Friday night dinner, Lorelai was surprised to find out Jason took a date to a function the previous night. When Jason popped by the Dragonfly Inn, she asked him about his date. Jason said his date was just a friend, and that he would have preferred his date be Lorelai, but she wanted their relationship to be secret.
Lorelai took Jason on a tour of Stars Hollow. When she invited him to Luke's Diner, he said he would stay in the car because he upset Luke that morning. When he noticed Luke watching them, he told Lorelai to find a new place for them to drink coffee. Emily then rung Jason to invite him to a charity event the next day, and then she phoned Lorelai to invite her. Lorelai wanted Jason to hide their relationship at the event but he thought they would be found out soon.
Emily wanted Lorelai and and Jason to pretend they were dating at the event. They agreed but Lorelai whined about it in the hope of annoying her and keeping the secret. She then met Floyd. Floyd found out they were dating when he sent a someone to spy on Jason. He revealed the relationship at a gathering of their parents. Floyd also tells them that night about Floyd's lawsuit against Jason and Richard. Jason argues with his father and begs Richard for his trust back.
At home, Lorelai and Jason appeared fine together where they speak about the evening. Jason says he is happy they no longer have to hide their relationship, which Lorelai agrees with. They drink to the positive side of the evening. However, Richard teams up with Floyd in the hope of salvaging his financial situation. They agree Jason needs to be out of their partnership.
When Jason finds out when they took every one of his clients, he files a lawsuit against Richard. Lorelai tells him that she cannot be with a man who is suing her family. Even though Lorelai had ended their relationship, Jason shows up the evening of the test run for the inn. Luke and Lorelai were becoming close romantically, but Jason tries to intervene by telling Luke that Jason and Lorelai were the ones who were right for each other. Luke confronts Lorelai and Lorelai says she and Jason are over. Luke and Lorelai kiss at the end of that episode.