Gilmore Girls: 5 Things That Proved Lorelai Should Have Stayed With Jason (& 5 Proving She Shouldn't)
Before Lorelai Gilmore started a whirlwind romance with Luke Danes on Gilmore Girls, she was in a brief romance with her childhood friend, Jason Stiles. The two met at summer camp when they were younger and rekindled their romance after running into each other again through her parents.
Due to the close relationship Jason had with Richard and Emily Gilmore, it made things tricky—but not impossible—between Lorelai and Jason. The two eventually broke up when the relationship with the Gilmores and Jason became too toxic. However, there are fans who believe that Jason was "the one who got away" and Lorelai's truest partner. But would the two make it through the mud?
10 Should Have Stayed With Jason: They're Both Outlaws
Jason and Lorelai are the outlaws of their own families. Lorelai never lived up to her family's high expectations of her. She didn't go to an Ivy League school, she had a baby out of wedlock, and she moved out when she was a teenager. Even as an adult, Lorelai still feels like the black sheep of the family.
Jason, on the other hand, started out on the right path with his family before going his own way. He became a Harvard graduate and started working for his father's company. He eventually left his father's company to work for the "enemy": Richard. Together, it was Lorelai and Jason against the world.
9 She Was Right To Leave: Jason Sued Richard
Jason and Lorelai could have been something great but Lorelai knew they would never work. After Richard went behind Jason's back and started working with Jason's father (leaving Jason out to dry), Jason had no choice but to sue Richard.
Lorelai was already on her parents' naughty list for life. If she was dating the man who sued her parents, things would have gotten worse for her. She had no choice but to end the relationship or her Friday night dinners would have been worse than they already were
8 Should Have Stayed With Jason: Emily Would Have Come Around To Jason
If Richard and Jason didn't have a bad fall-out, Richard and Emily would have come around to the idea of Lorelai and Jason being together. Emily and Richard despised Jason after Richard was forced out of the company. However, it was Emily who wanted to give Jason a second chance.
She's the one who forced Richard to take a meeting with him to see what he wanted. It was also Emily who made Lorelai and Jason "pretend" to be each other's dates at a black-tie event. She loathed Jason at first, but she would have come around to the idea. There were worse people Lorelai could have been with.
7 She Was Right To Leave: They Can't Sleep In The Same Bed
When Lorelai and Jason first sleep together at his house, he warns Lorelai that he can be a little quirky in his own space. He's a light sleeper who can't sleep with other people. It doesn't work for him. The only way Lorelai could spend the night at his house is if she slept in the guest bedroom.
Sure, he made the guest bedroom extraordinary for cases like these, but Lorelai is the kind of woman who enjoys intimacy and cuddling. There's no way she would be okay leaving her man's bed every single night to sleep alone.
6 Should Have Stayed With Jason: They Would Have Encouraged Each Other's Careers
In one episode of Gilmore Girls, Lorelai and Jason are spending time together but aren't really together. They're both on their phones the whole time talking to clients and construction workers. Jason was trying to get his business with Richard off the ground, and Lorelai was doing construction on the Dragonfly Inn.
Lorelai even called them an "all business corporate couple." Seeing how strong both of their work ethics were, these two could have inspired each other to do better. He's the only boyfriend of hers who wanted her to expand and grow.
5 She Was Right To Leave: Was She Only With Him For This Reason?
Was Lorelai only subconsciously with Jason to annoy her parents? In order to protect her relationship with him, she didn't tell her parents they were dating but it's the secrecy of it all the Lorelai may have liked.
She enjoyed dating a man no one knew about it. It was just them in their own little world and they had to pretend not to be friendly when they were in crowds. It was the game of the relationship that Lorelai liked most. As soon as people found out about Jason, things got messy and Lorelai ran away.
4 Should Have Stayed With Jason: He Was A Challenge
Jason and Lorelai were more alike than most people notice. Like Lorelai, Jason was also quirky, spoke fast, and understood her odd references. It was like they were speaking a language only they knew. It was his quirks that Lorelai found intriguing because she also had them.
Because of his business, Jason lived in the fast lane and always kept Lorelai challenged. She never knew what she was getting with Jason, which is something Lorelai liked. She hates monotony or when things are boring and stale. She never would have had that problem with Jason.
3 She Was Right To Leave: He's Everything She Didn't Want
Jason was wealthy, handsome, and worked with her parents. He grew up in the same lifestyle as Lorelai and knew a lot of the same heavy-hitters. He was a Harvard graduate and a wealthy man.
But do all of those traits sound like someone Lorelai would love? As amazing as Jason was, he's also everything Lorelai was trying to escape from when she left her parents. He may as well be another Christopher (and we all know how that worked out).
2 Should Have Stayed With Jason: She & Rory Would Have Been Taken Care Of
Lorelai is a very smart businesswoman and follows her gut in life. However, like many other people, Lorelai often found herself strapped for cash. As a single mother with pride, she hated asking for money when she was in need but she would do it as a last resort.
If she ended up with Jason, he was wealthy and successful enough to be relied on. If Lorelai ever needed a loan for the Dragonfly or for Rory, she could have easily gone to Jason instead of going to her parents or Luke.
1 She Was Right To Leave: Would Jason Move To Stars Hollow?
Jason is a fast-paced businessman who, presumably, enjoyed living close to the city because of business. Lorelai, on the other hand, loved Stars Hollow and never wanted to leave.
Stars Hollow was more than a town to her; it was home. It was a place where everyone knew and loved each other. She would have never left Stars Hollow for Jason. Likewise, one can't imagine Jason living in Stars Hollow and liking it.