Rory cheated on almost every single one of her boyfriends, except Jess. However, she did cheat on Logan with Jess — unbeknownst to him. During a fight with Logan, Rory went to Jess in Season 6, Episode 18 and kissed him.
Similarly, Dean pursued Rory while he was still married to Lindsey. Furthermore, while Rory is something of a serial cheater, she never cheated on Jess either. She did cheat on both Dean and Logan with Jess, which is not great, but it does prove that she was happiest with him and couldn't resist coming back.
Rory and Logan began dating in season 5 and broke up in season 7. They met in the courtyard at Yale her sophomore year and said goodbye at her graduation when she denied his marriage proposal. When the show returned 9+ years later, Rory and Logan are having an affair.
A Messenger, Nothing More.
However, on the night of its grand opening, Dean finds Rory collecting CDs at her house, and they end up sleeping together (Rory's first time). Not long afterwards, Lorelai returns home and sees the two hurriedly exit Rory's bedroom.
Rory losing her virginity to Dean at the end of Season 4 seemed like a pretty positive experience—except that, y'know, he was married at the time.
But one of the biggest surprises arrived at the very end, when Rory revealed to Lorelai that she was pregnant. However, it was never disclosed *who* exactly the father was... until now. Thanks to costume supervisor Valerie Campbell, we know it's none other than Logan Huntzberger.
"Gilmore Girls" The Party's Over (TV Episode 2004) - IMDb.
Gilmore Girls is a mostly beloved TV series, but the show still had storylines that were almost universally despised by fans. Rory Gilmore's decision to sleep with her married ex-boyfriend is one of them.
Logan Huntzberger (Matt Czuchry) may not be the greatest guy in the world, but he's the best match for Rory out of the men she dates. These two complement each other well and (usually) bring out desirable sides of each other. Logan is the classic playboy, and Rory seduces him into monogamy: a tale as old as time.
In Gilmore Girls: A Year in the Life, at the end of the Fall episode, Rory tells Lorelai she's pregnant, revealing the final four words Sherman-Palladino had in mind all along; “Mom?” “Yeah?” “I'm pregnant.” While not 16 years old like her own mother was, Rory is romantically unattached and without a steady job, ...
Rory and Logan break up, when Rory discovers Logan slept with other women during their break. Rory later decides to forgive him and they get back together, until Logan realizes Rory still isn't over the cheating and decides to do a stunt with the Life and Death Brigade.
At no point in A Year in the Life do we see the two of them hook up. But it would not be surprising to learn that, after their conversation at the Stars Hollow Gazette office, Jess and Rory got it on and we just didn't see it happen.
After ruining Dean's marriage, she proceeds to ruin his life.
Rory writes a letter to Dean while she is away, and Lorelai delivers it to him. 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.
Yeah, things just got complicated. 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 the end, Rory ends up alone, though her final words to her mother — “I'm pregnant” — should indicate this story is still far from over. “Gilmore Girls: A Year in the Life” is currently streaming on Netflix.
Dean appeared less frequently on Gilmore Girls starting in Season 4, as he eventually married Lindsay. Rory didn't react well to the marriage, and at the end of the season, Dean cheated on his wife with Rory, which resulted in Rory losing her virginity.
As for fans who hoped that Rory's first love Jess (Milo Ventimiglia) somehow impregnated her, Campbell quickly shoots down that idea. Why? Well, for starters, Rory and Jess never have sex in the the show's revival. "Seriously, guys, it's not immaculate conception," Campbell jokes.
They were what they needed from the moment
Jess Mariano's real-life counterpart Milo Ventimiglia argues that it made sense for the young couple to break up, as they were too young to know what they wanted or needed in the long run.
Paris and Rory's kiss in the seventeenth episode of season four was met with anticipation from viewers and the media, drawing attention from Fox News, Spin magazine, and other journalists.
Valerie Campbell, who worked on 2016's Gilmore Girls: A Year in the Life, has declared in a series of TikTok videos that Logan Huntzberger (Matt Czuchry) is the father of Rory's (Alexis Bledel) baby, ruling out the forgettable Paul (Jack Carpenter) and the Wookiee that Rory had a one-night stand with in the series.
Melissa McCarthy's Gilmore Girls character Sookie St. James and Jared Padalecki's Dean Forrester were two prominent Gilmore Girls mainstays who barely put in an appearance in A Year in the Life. Although both actors do show up in A Year in the Life, they're both only in the revival very briefly...
Do they have any children? The pair have one child. Poppy Kennedy McIlroy was on born August 31st, 2020. McIlroy took to Instagram to confirm the announcement, writing: 'Poppy Kennedy McIlroy, born August 31st, 12:15pm.
Dependent Personality Disorder in Gilmore Girls.