Dean was Rory's first real boyfriend on Gilmore Girls, and fans (and Lorelai) absolutely loved him. He was charming, handsome, devoted to Rory, and seemed like the ideal guy - especially in contrast to her other two main love interests, bad-boy Jess and rich-kid Logan.
However, Dean may not have been as perfect as he first seemed, especially when it comes to his dynamic with Rory. There were times that it was clear that the two weren't just ill-suited, but that their relationship was actually pretty toxic. Of course, a lot of this can be forgiven given their young age and the fact that it was the first real relationship either one had, but still... things weren't all Donna Reed, all the time...
10 Toxic: Cut Off Other Friends
Dean never really seemed to have other friends, and spent all his free time with Rory, or working. In fact, when Lane even asked to be set up with one of his friends, he told Rory that the two weren't even 'friends', they just kind of knew each other. Even later in the show, Dean is rarely seen with friends (except for his bachelor party, when a few pop up). Rory, too, essentially ditches Lane when they get together, until she is called out on it. Dropping friends for a relationship is never a good sign.
9 Perfect: Got Along With Family
Both Rory and Dean got along with the other's family, which is a great sign of a healthy relationship. Rory really liked Dean's younger sister, although we didn't see his parents much. And of course, Lorelai adored Dean (and not just because he could change her water jug, either). She was always happy to have him over and hanging out with her and Rory, and often said that she thought he was the best first boyfriend she could have wanted. Even Emily and Richard were fans!
8 Toxic: Pressure To Say 'I Love You'
When Dean first said 'I love you', Rory didn't feel comfortable saying it back yet - and although they had been together for a long time at that point, this was still her first relationship, and the first time she would be saying 'I love you'. But when she didn't reciprocate, Dean got upset, and put pressure on her to say what he wanted to hear.
7 Perfect: Grand Gestures
The grand gesture is a staple of on-screen romance for good reason - everyone loves the idea of a huge, sweep-you-off-your-feet moment... and Dean is really, really good at them. He comes up with sweet date ideas, gift ideas, takes her to a debutante ball, to a fancy dance, and even builds her a car.
Rory has her own set of grand gestures, too, such as her Donna Reed date night ideas. It's lovely to see both of them making a huge effort for the other.
6 Toxic: Making Fun Of Interests
Of course, one of those big date ideas is a little tainted by the fact that Rory only comes up with a Donna Reed date idea because she and Dean can't agree on how they feel about the Donna Reed show, and she makes fun of his ideas about it. He also makes fun of her love of reading - and even though it is in a patient 'loving' way, it's still a bit uncomfortable to watch them put each other down and hide it with a smile.
5 Perfect: Being Willing To Compromise
While they may not always see eye to eye, at least Dean and Rory show that they are willing to compromise. He may not love the idea of a big fancy dance at Chilton, or of her staying home to study, but he knows when to compromise for the sake of respecting her and making her happy. Similarly, Rory does make the occasional sacrifice for him, although this is shown less, probably because Rory is the main character!
4 Toxic: Totally Different Goals In Life
While no one really expected these two to go the distance (as high school sweethearts rarely do!), if they had tried to, it probably wouldn't have worked - because at the end of the day, they just wanted different things.
Rory wanted to go to an Ivy League school and then travel the world as a journalist... and Dean wanted to have a wife at home, and live in Stars Hollow. Clearly, those are life goals that just don't line up.
3 Perfect: Balanced Each Other Out
In the shorter term, though, Rory and Dean balanced each other out nicely. Rory pushed Dean to bigger goals, to trying harder, and encouraged him to go to college. Dean helped Rory feel loved, and protected, and gave her the kind of admiration that she craved, and confidence to explore her new Chilton world. For the time that they were together, they were exactly what the other one needed.
2 Toxic: Cheating
Things definitely didn't end well for Rory and Dean, as they ended up breaking up over Rory's obvious feelings for Jess (not forgetting the fact that she kissed him at Sookie's wedding, when she and Dean were still together). This was nothing compared to later in the series, though, when Rory and Dean were the ones who had an affair, sleeping together despite the fact that Dean was married to Lindsay. Cheating just isn't the sign of a good relationship, no matter what side of it the people involved are on.
1 Perfect: The First Big Love
No matter what their flaws, the first time that Rory and Dean were together was perfect was because they were each other's first love. Thankfully, by the time of the revival, it was clear that they could be polite to each other and just appreciate how important they were to each other once - and that's a big deal. Lorelai was right to call Dean the best first boyfriend her daughter could have, even if they weren't always perfect.
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