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Dean, the typical “boy next door”, came to Stars Hollow from Chicago and quickly fell for the quiet Rory just as she was about to leave Stars Hollow High for Chilton. At Rory’s 16th birthday party, Dean gave Rory a bracelet that he made for her and from that day on, Rory and Dean became a couple. In the beginning, they had the perfect relationship, complete with hand-holding and late-night calls. But their seemingly flawless relationship was ended when, on their three-month anniversary date, Dean told Rory that he loved her and she failed to reciprocate. Rory soon was able to work through her feelings and they got back together when Rory confessed her feelings for him. Just as their relationship had gotten back on track, another complication arose when Jess Mariano arrived in Stars Hollow and caught Rory’s eye. Dean, jealous of Rory’s obvious feelings for Jess, broke up with Rory at the Stars Hollow Annual Dance Marathon.

Dean rebounded with Lindsay Lister and after dating for a short while, Dean asked her to marry him despite his apparent feelings for Rory. After their marriage, Dean landed a job as a construction worker and continued working at Doose’s Market to earn enough money for the newlyweds to afford their own townhouse. In spite of Lindsay’s wishes, Dean continued to remain close to Rory, often talking to her over the phone, and once he realized that his marriage to Lindsay wasn’t working, he had an affair with Rory that ultimately led to divorce. After the bitter divorce, Rory and Dean tried once again to have a relationship, but when they realized that during their time apart their lives had taken two different paths, they broke it off and each went their separate ways.

Dean last appeared in season 5 and with Logan being a permanent fixture in Rory’s life, it is unlikely that he will return to Stars Hollow.

Jess Mariano, Luke’s nephew, came to Stars Hollow after his mother could no longer deal with his rebel-without-a-cause attitude. His father was no longer a part of Jess’s or his mother’s life, so he was sent to live with Luke in order to clean up his attitude. At first he rebelled from his new living arrangements by setting up pranks at a grocery store, stealing a lawn gnome, and taking all the baseballs from the Stars Hollow High baseball team. Though he almost failed out of school, Jess is very well read and has a vast knowledge of literature and other subjects.

His intellectual side caught the eye of Rory, despite the strong warnings from her mother not to fall for him. Though Rory was dating Dean, Jess worked to charm Rory away from Dean and soon won Rory over. They began dating after the Stars Hollow Annual Dance Marathon, but their relationship was ill-fated due to Jess’ lack of communication and his jealousy towards Rory and Dean’s now-friends only relationship. When Jess learned that he wouldn’t have enough credits to graduate, he left Stars Hollow for Venice Beach, California where his father was living. Rory and Jess remained out of touch until his mother returned to Stars Hollow for her wedding. Jess came to town to escort his mother down the aisle and after confessing his love to Rory, he went to her dorm to ask her to run away with him. She declined and Jess once again disappeared from her life. After a year, Jess yet again returned to Rory after getting his book published to tell her that he couldn’t have done it without her. Jess’s reappearance in Rory’s life led her to reconcile with her mother and break away from the rich lifestyle she had been living.

Jess currently works at his own bookstore/publishing company/art house working on his book in Philadelphia.

Jason Stiles, nicknamed “Digger” by his father, is the son of wealthy parents Carol and Floyd Stiles. During his childhood, Jason attended the same summer camp, Camp Chataguay, with Lorelai and Christopher, Rory’s father. Lorelai’s father, Richard, and Floyd were also business partners at Gehrman-Driscoll Insurance Corporation so Richard had known Jason since he was a child.

When Richard quit Gehrman-Driscoll Insurance Corporation to start his own business, Jason approached Richard about being partners and when Richard accepted his proposal, he was re-introduced to Lorelai at a family dinner. Though Lorelai originally resisted his advances, Jason’s persistence in pursuing Lorelai romantically paid off and the two began dating, their first date being at a grocery store. They kept their relationship hidden from their parents, in an attempt to avoid family controversy, but when Floyd decided to sue Richard’s company, and Jason, he informed the Gilmore’s of Lorelai and Jason’s relationship. After Floyd and Richard settled their differences and avoided the lawsuit, by cutting Jason off from both companies, Jason decided to sue Richard, leading Lorelai to break it off with him. His efforts to win her back proved fruitless – Lorelai had moved on with Luke Danes. Jason left Connecticut to start over and hasn’t returned to Stars Hollow since.