Lorelai and Max meet in the first season of Gilmore Girls and become instantly curious about each other. It was Rory’s first year at Chilton and both ladies wanted to make a good impression. Being young, gorgeous, and spontaneous, Lorelai got a lot of attention from the men at the school but she only had eyes for Rory’s teacher, Max.

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The two enter a secret relationship with the best intentions but when things get too serious, Lorelai exits without much of an explanation. But after a short break, the two get back together and are better than ever. Or are they? After a quick engagement, things went downhill for Lorelai and Max. Was he the one that got away or were they never meant to be?

10 Great Together: Rory Loved Max

It was weird for Rory when she discovered her mom was dating her teacher — especially given how she found out. Lorelai was trying to keep her relationship with Max under wraps until she knew what they were but the cat was out of the bag when Rory saw Max walking up to her house.

It took some time but Rory ended up liking Max (or as she called him, Mr. Medina) with her mom. After Lorelai and Max broke up, Rory opened up to him in a gut-wrenching moment and said she really wanted him to be her stepfather.

9 Never Made Sense: They Didn’t Discuss Anything Important

Lorelai was understandably nervous to tell Luke that she was engaged to Max. It was painfully obvious to everyone but Luke and Lorelai that they had crushes on each other, which is why she waited to tell him. When she did, Luke knew it wasn’t going to work.

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He immediately asked her where they were going to live and brought up deep questions that she had no answers to. It turns out that she and Max didn’t discuss anything important. This proved that they really didn’t know each other well enough to get married.

8 Great Together: He Would Have Fit In Perfectly With The Gilmore Gang

Max didn’t meet the Gilmores in the best of atmospheres — Lorelai and Emily were fighting at the time — but he would have gotten along beautifully with Lorelai’s parents. Max worked as an esteemed teacher at Chilton and was highly educated. He was handsome, respectful, and knew how to carry a conversation. And while Emily and Richard didn’t know him well, they were both equally ecstatic about the wedding and were happily planning everything down to the minute. Having a partner that got along with Richard and Emily could have made Lorelai’s life easier.

7 Never Made Sense: Lorelai Wouldn’t Allow Max To Be A Parent

When Max and Lorelai went on a double date with Rory and Dean, Max wasn’t sure how to handle the whole Rory-and-Dean-thing. Does he give her a curfew? Does he ask Dean to leave? Max wasn’t sure where he stood.

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When he asked Lorelai about his role in Rory’s life, Lorelai told him not to worry about it and that she would handle the disciplining, etc… This upset Max. Was he going to ever have a say in the Gilmore household?

6 Great Together: There Was No Lack Of Passion

Lorelai is the kind of woman who flies by the seat of her pants. She’s a passionate woman who can’t help herself when she’s attracted to someone. She’s slept with Christopher on and off for years because of their deep connection to each other. And it appeared that she had the same kind of connection to Max. Their passion for each other was different than her passion with Luke.

5 Never Made Sense: Favoritism

With Max as a teacher at Chilton, he had a hard time being both an educator and a close figure in Rory’s life. He didn’t want to show favoritism towards Rory just because he was trying to get on her good side with Lorelai.

Max breaks teacher mode and ends up kissing Lorelai when she visits for Parents Day. And unsurprisingly, Paris saw everything and told the whole school. If Max wasn’t able to keep his personal life out of the classroom, he may have had to choose between Lorelai and Chilton.

4 Great Together: They Were Realistic About Their Partnership

The smartest thing Max and Lorelai did in their relationship was dissect it. They both knew dating each other came with problems. They were too hot too soon. They both agreed to take some time apart and think about their relationship and the direction it was going in. This could have broken them but it made them stronger. After months of being without each other, they started with daily phone calls before diving back into dating again. This was one of Lorelai’s more adult decisions.

3 Never Made Sense: His Proposal

At the end of the first season, Max is furious when he finds Luke and Lorelai talking inside Lorelai’s house. He didn’t understand how close they were and hated their bond. The two begin arguing about Luke when Max says “There’s only one thing I can think of that could solve [fighting].”

Lorelai assumes he’s going to break up with her but out of nowhere he says “we should get married.” Lorelai is shocked and has nothing to say. She’s upset at his proposal because it sounded desperate and was anything but romantic.

2 Great Together: He Was Her Total Opposite

They say that opposites attract. Max is accomplished, sophisticated, and well-read; Lorelai is messy, spontaneous, and wild. The two were each other’s perfect balance. Max gave Lorelai the stability she unknowingly needed; and Lorelai added color to Max’s world. It also helped that Rory was the epitome of the perfect stepdaughter.

1 Never Made Sense: He Didn’t Want To Be In Connecticut Forever

Max was a beloved teacher at Chilton but he didn’t want to be in Connecticut forever. He once taught at the University of Toronto in the summer months, which proved he was interested in trying out other avenues of education. When he and Lorelai broke off their engagement, he said that he moved to California where he taught a class at Stanford.

If Max was with Lorelai, she wouldn’t have ever left Stars Hollow where her friends, home, and job were to support his career across the country.

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