Terry and Dana began dating when they attended Hamilton Hill High School. Her father disapproved of the relationship because of Terry's checkered background, but Terry worked hard to prove his worth.
Their relationship was a close one; when he had her drop him off at Wayne Manor, she expressed concern about leaving him alone in the middle of nowhere, and he responded with the same tenderness.
When Terry started being Batman, it put a strain on their relationship, with his frequent absences, and often last-minute cancellation of their plans. He often covered these absences with his new "job" for Bruce Wayne and the new family responsibilities caused by his father's death. Later, their mutual friend Maxine Gibson, who learned Terry's secret identity, also helped cover for him.
As time went on, Dana devised her own explanation for Terry's attachment to Wayne: that he had become a father figure to replace the one Terry had lost. This made her feel sympathetic (and she was more right than either she or Terry knew, as Bruce Wayne would later be proven to be Terry's biological father).
Still, on at least one occasion Dana broke up with Terry over being stood up once too often. Unaware that she was being stalked by Ratboy, an abandoned child who had grown up in the sewers, she mistook a mash note from him as coming from Terry and offered to meet with him. She was abducted by Ratboy and kept in his underground lair, but she showed considerable bravery, first trying to escape through the sewers by crawling on all fours, and then improvising a trap for Ratboy that ended up torching his lair, and probably him along with it. Severely traumatized, Dana was approached by Terry afterwards, very contrite, and surprised him by hugging him closely.
Max once suggested to Terry that Dana could be trusted with his secret, and should be if he wanted to keep their relationship alive. Terry refused flatly, citing concern for her safety.
Nevertheless, the two continued dating after they left high school for fifteen years, and at some point during that time (possibly after the events of Batman Beyond: Return of the Joker) she became aware of his identity as Batman. He constantly warned her that she would be in danger if anyone ever discovered his secret, but she refused to leave him.
When Terry discovered his true lineage, he became disillusioned with his identity and imagined himself breaking up with Dana at last, seeing himself as "cursed." But on the advice of Amanda Waller, he came to grips with his past and took her advice to "take care of the people who love you." After this conversation, he planned to propose marriage to Dana.
- There is a line in Paul Dini's screenplay of Batman Beyond: Return of the Joker, from the scene in which Terry is explaining to Bruce why he wants to go on being Batman. Terry says that Dana's father's disapproval is a constant reminder that he'll never completely erase his criminal past.
- Season One
- Season Two
- Season Three