Rory Gilmore has a pretty great life on Gilmore Girls. She gets to live in Stars Hollow, a small town where everyone cares about each other, and while it's too bad that her dad is absent, her mom more than makes up for that loss. Fans watch Rory experience love and heartbreak over the show's seven seasons, and any hard times in her life are always balanced by fun movie nights with Lorelai.
Rory falls in love three times, although fans have different ideas about who her true soulmate is. Her boyfriend Logan can be horrible, and even Dean Forester, who is widely considered a great TV partner, has his negative moments on the series.
He Complains About Rory's Busy Schedule And Ambition
In the season 2 episode "Hammers and Veils," Rory starts freaking out that she won't get into Harvard unless she has more after-school activities on her application. It's a totally legitimate thing to worry about, as it's her dream to get into an Ivy League school.
Dean complains that Rory is so busy and he seems threatened by how ambitious she is. This isn't supportive because he should realize that while she wants to spend time with him, she cares about her future.
He Dumps Rory In A Cold, Cruel Manner
Dean may have romantic things to say to Rory on a regular basis, but when he dumps her in the first season after she doesn't say she loves him back, it's cold and cruel.
He tells her the relationship is finished and she has no chance to talk to him. He sets up a lovely evening with a fancy dinner and even gives her a car that he's fixing up, and it feels manipulative that he would have certain expectations of the evening.
He Breaks Up With Rory A Second Time In Front Of Everyone
Many fans love watching Jess and Rory flirt with each other, although they have their own problems once they do start seeing each other.
Even so, it's horrible when Dean breaks up with Rory for a second time and does it front of all of Stars Hollow. A dance competition isn't exactly the best setting for this, especially since he's so angry and loud about it. Rory needs someone who can treat her with more sensitivity and who knows that there's a time and a place for that kind of discussion.
He Cheats On His Wife And Has Sex With Rory
It seems fair to say that Gilmore Girls fans didn't think that Rory and Dean would sleep together when he's married in the fourth season. It's odd that Rory doesn't seem to think that there's anything wrong with this and that Dean would cheating on his wife.
This is one of the worst things about Dean and it's hard to root for him after this moment. Any good will he had with fans was pretty much gone from this point on.
He Fights With Other Guys Over Rory's Affections
From Tristan Dugray to Jess Mariano, Dean never stops fighting with over guys over Rory.
He seems to think that he's her knight in shining armor and it's actually pretty creepy. Instead of being calm and mature, he gets into a physical fight with Jess at one point. Since Dean is supposed to be so sweet and caring, this isn't behavior that Gilmore Girls fans would expect from him.
He Puts Lorelai In An Awkward Position
It's true that Lorelai likes Dean more than Jess, although she gets mad when Dean and Rory sleep together. But ultimately, Lorelai thinks that Dean is a nice guy and that he always has good intentions with her daughter.
Dean puts Lorelai in an awkward, weird position when he says that he knows that Rory has a crush on Jess. What is Lorelai really supposed to say? There are a few times on the show when Dean shows his immaturity and this is one of them.
He Acts Desperate To Stay With Rory
Dean doesn't do himself many favors in the second season of Gilmore Girls. In the episode "Back in the Saddle Again," he feels like Rory doesn't love him anymore.
Sure, it makes sense that Dean would be envious of Jess and that he would understand that his girlfriend had feelings for someone else. But he acts super desperate about it, and it's not one of his best moments. He shouldn't act like Rory is the only one for him and he can't imagine not being together, as he's the one who breaks up with her in season 1. He also knows that he doesn't want to go to college and Rory does, so there's always that looming in front of them.
He Marries Lindsay Even When He Knows He Loves Rory
Lindsay isn't a good match for Dean and their marriage is random and weird; he should never become her husband.
He marries Lindsay even though he knows that he loves Rory. Even Luke knows that Dean is still hung up on his ex-girlfriend, which says a lot since Luke doesn't like to get involved in other people's business. Dean should own up and realize that he's not being fair to his wife.
He's An Angry Person
It's never attractive when someone lets their anger get the best of them, and this is something that Dean does on a regular basis.
Jess is known for being the show's bad boy and while Dean is supposed to be the "good guy," he doesn't always act like it. He gets upset when things don't go his way or when Rory wants to have some time away from him, and it's strange that he doesn't learn how to settle down.
He's Too Old-Fashioned
Rory and Lorelai act like the same person a lot of the time, but it's tough to picture Lorelai cooking dinner for someone she was dating.
Rory, however, does this in the first season, as Dean is an old-fashioned person who believes women should be domestic goddesses. While he does support Rory and he likes her intelligence, it's weird that he has these beliefs when he's only in high school. He doesn't seem very progressive.