‘Gilmore Girls’: Do You Remember Everyone Lorelai Gilmore Seriously Dated?

There was a lot to love about Lorelai Gilmore on Gilmore Girls, but there was also a lot to dislike. Her manic romantic relationships were a point of contention for fans of the show for seasons. While she ended up with the man that many fans believed was her true love, there were more than a few potential suitors. Do you remember all the men that Lorelai seriously dated during the show’s original run?

Lorelai almost marries the English teacher

Lorelai makes it pretty clear that up until Rory enters Chilton, she didn’t do much dating. That doesn’t stop her from striking up a little romance with Rory’s English teacher, Max Medina. Admittedly, Max and Lorelai are a bit of an odd pairing and his pursuit of her borders on a little creepy.

Lorelai and Rory
Alexis Bledel as Rory Gilmore, Lauren Graham as Lorelai Gilmore. | Mitchell Haddad/CBS Photo Archive via Getty Images

He pursues Lorelai almost immediately, even though Rory is his student. The whole thing is very clandestine. When they break up and eventually get back together, he proposes during an argument. The only one who has a clear head about the whole thing is Luke. Luke manages to point out that Lorelai and Max haven’t discussed having children, where they would live, or if they were going to combine their finances. The entire thing is a bit absurd, and most fans agree that not marrying Max was a smart move on Lorelai’s part.

Lorelai quietly dates a businessman before he disappears from the show

After Max, Lorelai takes a little break from dating, save for one disastrous date with Jackson’s cousin, Rune. She meets a businessman named Alex during a seminar, and the pair have a pretty amazing first date. They try out a bunch of coffee, and Alex seems like he might just be the man Lorelai is looking for. The relationship doesn’t last long though.

In fact, fans never find out what actually happened to Alex. The last time fans see Alex is when he scores four tickets to a Broadway show in New York. The date goes well, and Lorelai is allegedly seeing Alex throughout Season 3, but he’s never mentioned again. For all we know, he’s still waiting for Lorelai to call him back.

Lorelai connects with a childhood friend

Lorelai finds an unlikely romantic connection with her childhood friend, Jason Stiles. True to form, however, there is a complication. Jason is Richard Gilmore’s business partner and the bane of Emily Gilmore’s existence. Lorelai only accepts a date with the insurance man because she knows it will annoy her mother.

Regardless of how the pair get together, they seem to enjoy each other and are accepting of each other’s quirks. Jason doesn’t seem to take it too personally when Lorelai hates his decision to book a private room for dinner, and Lorelai is pretty calm about the fact that Jason doesn’t want her sleeping in his bed with him.

Everything goes off the rails when Jason is forced to sue Richard. The couple breaks up, and while Jason does try and win her back, it’s not meant to be. While the pair didn’t make it long-term, fans still believe it was a good pairing. It is never revealed if Richard settled the lawsuit with Jason.

Luke can finally see her face

Just as things were wrapping up with Jason, Luke finally figured out that he wanted to be with Lorelai. He invites her to his sister’s wedding, and while things go well, the pair are left in kind of a grey area. Neither Luke nor Lorelai knows if they are actually dating. That’s all figured out once they kiss at the opening of the Dragonfly Inn, and everything seems right with the world. Wait, there’s a problem though, Emily and Richard hate the idea of them together.

Emily’s plot to break up the pair works and they spend several episodes apart, pining for one another before reconnecting. One yacht-stealing incident later and they are engaged, but a mysterious daughter shows up, thwarting their relationship once again. Eventually, the pair get it right, but the back and forth between Lorelai and Luke was truly gutwrenching for fans of the couple.

The Christopher chronicles

While Lorelai ends up with Luke in the end, her second most significant relationship has to be Christopher Hayden. As Rory’s father, Christopher walks in and out of the lives of the leading ladies several times over the show’s seven seasons. They almost give their relationship a try in Season 3, but a pregnant Sherry breaks up the plan. He tries to win her back in Season 5, effectively destroying his chances with her for the foreseeable future.

Christopher, however, will never go away, and once things go south with Luke, he’s waiting with open arms for Loralei. While the pair may have seemed like the perfect couple who just couldn’t get their timing right, a lot was keeping them apart. Christopher and Lorelai were both incredibly headstrong, they were both prone to shutting down when they didn’t get their way, and neither took criticism well. The troubling personality traits meant their short-lived marriage was never going to work, and it didn’t. Before long, Christopher was out of the picture.