Taking place a few months after Tangled and before their marriage in Tangled: Ever After, Eugene has found a home in Corona Castle, living alongside Rapunzel and her parents. While Rapunzel has apprehensions toward her new life as a princess, Eugene couldn't be more ecstatic with his newfound life. During Life After Happily Ever After, he reveals to Maximus and the pub thugs that he plans to propose to Rapunzel during her coronation weekend, having already practiced his speech and purchased a ring. Once he finally proposes, however, she rejects him and storms out the room. Eugene is left confused and tries to talk things over with Rapunzel, but when he visits her bedroom, he instead finds Pascal covering for the princess, who secretly left the castle with her handmaiden (and Eugene's rival) Cassandra. Knowing Rapunzel's overprotective father will blow a fuse should he learn of Rapunzel's actions, Eugene teams up with Pascal to distract the king until Rapunzel returns.
The following morning, Eugene and Pascal hear a commotion coming from Rapunzel's bedroom and storm in to help. Eugene finds that Rapunzel's 70-feet of magic hair has mysteriously returned, and what's worse, she refuses to tell him how this came to be. Though he reassures Rapunzel that she can trust him with anything, Eugene helps her and Cassandra cover up the return of the hair from Rapunzel's parents. Rapunzel eventually gets the idea to hide it in an oversized wig, which proves to be successful. As Rapunzel spends the day with her parents, Eugene tries to get answers from Cassandra, who berates Eugene for only focusing on what he wants out of life and ignoring Rapunzel's own personal struggles. Later on, the day of the coronation finally arrives. At the ceremony, the royal family is attacked by a band of pirates out for King Frederic's head. Eugene joins Rapunzel and Cassandra as they successfully fight off the villains, but the truth behind Rapunzel's hair is voluntarily revealed to the king and queen in during which.
Fearful that the return of Rapunzel's magic hair will attract danger similar to Mother Gothel, King Frederic forbids his daughter from leaving the walls of the kingdom without his consent. Rapunzel mourns the loss of her freedom in her bedroom, though she is soon visited by Eugene who apologizes for pressuring Rapunzel with the surprise proposal, who in return apologizes for her poor reaction. He confesses that he is unsure as to why she would reject his proposal, but assures that he is willing to stand by her side to help understand her struggles as best as he can and take their romance slow. He also promises to be patient with her at Rapunzel's request, strengthening their relationship significantly.
As seen in the episode What the Hair?! (one week after Tangled: Before Ever After), Rapunzel has still yet to tell Eugene the truth about how her hair returned, claiming she simply "woke up with it" one morning. Because of this, Eugene starts to question his relationship with Rapunzel, though she eventually refuses to keep secrets from Eugene any longer and fully confesses the truth of how the hair returned, including the fact that Cassandra was the one that helped her escape Corona. Eugene initially plots to turn Cassandra in but decides not to after realizing how important she is to Rapunzel. He nevertheless shows gratitude in Rapunzel's honesty.
Afterward, Eugene and Rapunzel continue to hold a healthy relationship. Despite this, Eugene has other insecurities to face, such as his abilities beyond thieving (which are focused on in Fitzherbert P.I.), and his relationship with his future in-laws (as shown in In Like Flynn and The Way of the Willow).
He still holds his rivalry with Cassandra, which culminates in Cassandra v. Eugene. In the episode, Rapunzel forces Eugene and Cassandra to work together to escape a prison cell. Following the escapade, they reach somewhat of a common ground, though they are still prone to bickering. Some of Eugene's backstory is also explored.
In The Return of Strongbow, Lance Strongbow returns to Corona in hopes of enlisting Eugene to assist the former in a heist, though, in a turn of events, Eugene and Rapunzel get Lance to reform. This would allow Eugene and Lance to continue their longtime friendship, at adulthood.
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- In the past, he has gone by the name Flynn Rider.
- In the episode, Fitzherbert P.I., Eugene reveals that he knows Italian from his days as a thief.
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