It isn't until Lindsay discovers the letter that she realizes Dean cheated on her, throws his belongings publicly out their apartment window, and they divorce. Afterwards, Dean and Rory begin dating, but the affair and their time spent apart has clearly taken its toll.
Rory and Dean Forrester's clandestine hookups are largely blamed for Dean's divorce from Lindsay Lister less than a year after their wedding. While we get how Rory gets some blame for the whole situation, we don't think she was to blame for their divorce, not even a little bit.
"Gilmore Girls" A Messenger, Nothing More (TV Episode 2004) - IMDb.
Having finally admitted they are separated, Richard and Emily formalise things by having Richard move into the pool house, with the girls splitting Friday nights between the two of them. Dean's marriage to Lindsay comes to an abrupt end when she finds a letter Rory wrote to him about their night together.
Season 4: Rory Loses Her Virginity To Dean
Dean and Rory don't actually spend a lot of time around one another during season 4 of Gilmore Girls. Rory is busy trying to find her footing in college and Dean is navigating married life.
Similarly, Dean pursued Rory while he was still married to Lindsey. Furthermore, while Rory is something of a serial cheater, she never cheats on Jess, either. She did cheat on both Dean and Logan with Jess, which is not great, but it proves that she was happiest with him and couldn't resist coming back.
Seven years after Netflix dropped Gilmore Girls: A Year in the Life, we finally have an answer to who Rory's baby daddy is, at least, according to the costume supervisor: It's Logan.
However, Rory felt like the relationship was moving too fast for her and the two broke up. While they eventually got back together, the arrival of Milo Ventimiglia's character Jess Mariano drove them apart again. Rory discovered she had more in common with Jess than the working-class Dean.
Emma Winchester is the daughter of Dean Winchester and Lydia. She is an Amazon warrior, trained to kill her father, but she refuse to go through it and was accepted by her family.
Later, Rory wrote a letter to Dean about it, which then Lindsay discovered and asked him for a divorce. Rory and Dean try to give their relationship another try after that, but sadly, it doesn't work out. Presumably, Dean moved on to marry Jenny and start a family.
Since he couldn't have the perfect small-town relationship with her, he just took the chance to have one with his current girlfriend, Lindsay. He got the attention that comes with a young marriage, so he got what he wanted! Attention and validation. He finally wasn't going to have the “Rory's ex” label.
Rory (Alexis Bledel) dropped the pregnancy news to her mom Lorelai (Lauren Graham) in the final scene of the series finale — but she never revealed who fathered her as-yet-unborn child, and the question has lingered in fans' minds for years. Until now! Gilmore Girls Cast: Where Are They Now?
“Raincoats & Recipes”
Luke and Lorelai consummate their romance with a passionate first kiss for the ages. (“Will you just stand still?”) Meanwhile, Rory has sex for the first time with Dean, her ex-boyfriend and first love, who's now married.
Dean — Her First Love
It is highly unlikely they've been together romantically in recent times as they seem to have moved on, and he is a happily married family man. For this reason, Dean is most likely not the father of Rory's baby.
Dean Forester: Dean is Rory's first boyfriend ever, who she meets at the local high school before she attends Chilton and after he moves to Stars Hollow. He's also her first kiss and the man she loses her virginity to. They embark on three different relationships during the duration of the show.
Rory doesn't end up with Jess, Logan, or Dean, who is married with three kids and a baby on the way. She ends up with a baby. Needless to say, it made for a polarizing ending that fans have been picking up for a while.
In Plucky Pennywhistle's Magical Menagerie, Dean mentions not wanting to get into bed with any more women in case he makes more babies, a clear reference to Emma. She was killed by her uncle. She is also the second direct relative that Sam killed with the other being Samuel Campbell, Emma's great-grandfather.
When Dean died, he left Sam alone, and he hasn't quite forgiven himself for that. Though we know that Sam is okay (he eventually marries and has a son, whom he names Dean in honor of his late brother), Dean is still the over-protective big brother he's always been.
When Dean had first met Ben Dean considered the possibility that Ben might actually be his son. Lisa confirmed to Dean that Ben wasn't his son and his similarities to him was due to her 'type' that she hooked up with that Dean had fallen under.
Jess and Rory had more in common intellectually than she did with Dean. It was good for Rory to date someone who was on her level as they were able to have more interesting and intelligent conversations.
However, in the end, Luke and Lorelai did finally end up getting married in the last episode, years after their failed first attempt in Gilmore Girls season 6.
Lane's Overall Journey
By the end of the show, we see Lane still married to Zack and taking care of their twins Steve and Kwan. It's not the life that she envisioned, but she made it work. In A Year in the Life, the twins are grown up and Lane and Zack are still living in Stars Hollow, and that's about it.
Rory is 32 now, twice the age Lorelai was when she got pregnant with Rory. Had this pregnancy put a stamp on the end of the original series, when Rory was in her very early 20s, it would not have felt as fitting as it does now. Like her mother, Rory has, as far as we know, gotten pregnant unexpectedly.
But the following autumn, they meet up in Stars Hollow for one last romantic night together. Soon after, Rory realizes she's pregnant. Campbell tells fans in her TikTok video that "Gilmore Girls" creator Amy Sherman-Palladino always intended for viewers to infer that the baby's dad was Logan.
Gilmore Girls: A Year in the Life ends with Rory revealing her pregnancy, but the father of her baby is never confirmed.