Personality
When first introduced, Flynn is presented as arrogant, backstabbing, and trouble-making. He unabashedly committed acts of thievery on the royal family of Corona, all to achieve a selfish lifelong goal of becoming as wealthy as humanly possible. Despite these antagonistic traits, Flynn viewed such acts as mere means to boost his ego which, at the start of the film, was comedically inflated, to the point where he would rely on his supposed charisma to sneak his way out of a potentially dangerous situation.

As mentioned above, Flynn is also rather comedic, whether it's intentional or not. He has a peculiar relationship with the palace horse, Maximus, who he constantly finds himself at odds with throughout the film, being that they were highly different on the moral spectrum at the start of the film. Even so, they managed to form a meaningful partnership, and eventual friendship; initially for the sake of Rapunzel, though they were shown to have become fond of one another over time. Despite viewing himself as charming, a recurring situation involving Flynn includes the thief being looked down upon by other characters (such as the Pub Thugs or the palace guards) who would often perform acts that would purposely result in Rider's humiliation, such as having the portraits of his "Wanted" poster be depicted with cartoonishly large or unattractive noses, much to his annoyance. He can also be a bit dimwitted at times.

Despite all of this, Flynn's arrogance is revealed to provide a false sense of optimism as the thief is highly vulnerable and capable of showing and feeling legitimate emotion. This is seen after he meets and forms a relationship with Rapunzel. The princess' refusal to be fooled by Flynn's charisma, and genuine interest in his life and struggles, would be the first motivators to dropping the "Flynn Rider" persona and accepting who he alluded to being in the orphanage, which was caring, starry-eyed, and selfless.

Once his facade is dropped, and Eugene truly opens up to both Rapunzel, and himself, he is portrayed as a loving, loyal, and protective companion. For Rapunzel, he was willing to give up his life of thievery to remain by her side, in hopes of starting a new life for both himself and the princess, believing they've both deserved second chances after facing experiences less than pleasant over the years.

Unlike Gothel, Eugene viewed Rapunzel as a person, caring for her feelings, rather than her magical hair. In spite of being greedy at the start of the film, Rapunzel's magic was never a concern to him, nor did he once ponder on the thought of using her for her powers to obtain wealth. When those who attempt to do so came about, such as Gothel, Eugene takes action and becomes a fierce protector, willing to go against foes twice his size, if necessary. He also proved himself to be selfless in this instant, risking his life for Rapunzel's safety, despite being given the chance to leave a situation safely.