On Gilmore Girls, Dean Forester was Rory Gilmore's longtime love interest and one of the hardest-working people in Stars Hollow. And while Dean and Rory didn't work out, he finally got his life in order and got the family life he always wanted (as seen in A Year in the Life).
The more viewers got to know Dean, the sadder his life became. Dean had demons inside his head and bigger issues at home that weren't given the screentime they deserved. Dean is a great young man, but he sure got the short end of the stick in the series.
He Was In A Loveless Marriage To Get Over Rory...
Dean and Rory weren't even broken up for a full year by the time he proposes to Lindsay. This means he and Lindsay were barely dating long enough to know if they loved each other by the time they became engaged.
When Dean tells Rory he and Lindsay are engaged, he's obviously seeking her approval and was almost looking for her support. On the night of his bachelor party (a night before the wedding), a drunk Dean falls into bed and says he missed Rory. It's crystal clear: he married Lindsay to get over Rory.
... And Then Broke Up His Marriage Because Of Rory
Dean is 100% responsible for the death of his marriage. Lindsay tried hard to be the perfect homemaker and to praise her husband but he was far too consumed with his own shortcomings to notice his perfect wife at home.
And although Dean cheats on Lindsay with Rory and probably never really loved Lindsay, one can't help but feel bad for him. He destroys a woman's life because he isn't over his ex-girlfriend. The inner torment he goes through just to find himself is crushing beyond belief.
Never Good Enough For The Gilmores
Dean's first encounter with Richard and Emily Gilmore is a disaster. Dean is the first of Rory's boyfriends they meet and their expectations were high. Rory and Lorelai warn Dean before entering the lion's den but even Rory doesn't expect the night to go so horribly.
Richard immediately quizzes Dean about his upbringing and his education. He warns Dean that Rory is destined for better things and that he shouldn't hold her back (which was never Dean's intention). The evening goes so horribly that Rory scolds her grandparents and she and Dean left in a hurry.
Constantly Fighting For Rory's Heart
As protective and sweet as Dean is to Rory, he isn't perfect. He is incredibly jealous and needy of a woman who is busy with her education. But Rory isn't exactly a peach either. She lies to Dean and hides things from him when they're dating.
Dean was constantly battling other men for his girlfriend's heart. He goes against Tristan at the start of their relationship, he battled Jess over the years, and he finally gives up on Rory when he sees her with Logan.
Didn't Think He Was "College Material"
When Rory and Dean were dating, the topic of conversation always revolved around Rory's hopes and dreams. But what Dean's? Dean was satisfied with going to community college after high school but it doesn't seem like a priority for him. When he and Rory break up, he tells her he applied and got accepted into Southern Connecticut State College. However, fans think he does this to appeal to Rory.
When he and Lindsay get married at the tender age of 19, Dean starts working more jobs to please his wife and her family, so he stops going to school. If he never married Lindsay, who's to say he wouldn't have been a college graduate?
Never Had A Chance To Be A Kid
Dean never had a chance to be a kid. He worked multiple jobs as a high school student and then got married at 19. He never had a period of time where he could let loose, live in a dorm, or be a single man in a new town. Dean has always acted older than he is and that results in him making incredible mistakes because he wasn't ready for the responsibilities thrown his way.
Had No Say In His Own Wedding
Nothing was more telling of Dean and Lindsay's relationship than when he says it's "her wedding" while talking to Rory. Lindsay and her mom are seen running around the gazebo planning the wedding while Dean stays out of the way and lets Lindsay do her thing.
Lindsay and her parents had the upper hand when it came to Dean. He tells Luke her family is the most selfless people he's ever met, which is probably why he complies with so many of their demands.
Lindsay Aired His Dirty Laundry
When Lindsay read Rory's letter and finds out that Dean was cheating on her, there was no chance for reconciliation. Dean had been treating Lindsay horribly for months and his indiscretion is the cherry on top.
To embarrass him to his core, Lindsay dumps all of Dean's belongings in the front yard while yelling at him. At that moment, the entire town knows what happened between Lindsay, Dean, and Rory. Now, Dean deserved everything Lindsay throws his way but that doesn't mean it's not a sad moment in his life.
Where Were His Parents?
Where in the world were Dean's parents? Viewers rarely see them! There were plenty of times that would have been great to hear Dean's parents' points of view but they were nowhere to be found. He does everything for Rory and Lorelai and then does everything for Lindsay and her mother when they get married. He stays with Lindsay's parents and says how helpful they are. But were his own parents not helpful? It looked like they weren't as involved in Dean's life as he might have needed them to be.
Was He Better Off In Chicago?
Dean moved to Stars Hollow as a teenager from Chicago. Rory is the one who helps him get to know the town and hooks him up with a job. However, Dean's life in Stars Hollow hasn't been rainbows and daisies.
He gets into multiple fights with anyone who shows interest in Rory (Luke even thought Dean was bad news), he stops going to school to focus on his bride, and he has an affair with the town's angel, which leads to his divorce. One can't help but wonder if his life would have been on a better path if he stayed in Chicago.