As Tuxedo Mask, he was the object of Usagi's interest (along with many other guys), but as Darien, he was the object of her annoyance...until they revealed identities.
Locked together in an elevator (again), a trap set up by Zoicite, Darien swallowed his pride and toled Usagi the hardships of his past. "I keep getting this recurring dream...there's this moon princess waiting for me, she keeps begging me to bring her this Imperium Crystal....I think she can tell me who I am" (Crystal Clear Destiny). At that tendering moment, Zoicite sends a rave of fire to end Tuxedo Mask, (yes, she does know Darien's identity). Revealing her identity, Usagi transforms to Sailor Moon in front of Darien to save him and herself from Zoicite's fire of hatred. "It's her!.....Serena's Sailor Moon!" Feeling that "special bond" Darien transforms to Tuxedo Mask in front of Usagi's and Zoicite's eye. "Walah....Cranky ol' Darien my dream hunk?...This is going to take some adjusting to!" But after a perilous attack from Zoicite, our dear Tuxie falls and struggles for his life in Sailor Moon's arms. A lone tear from her eye falls, forming the Imperium Crystal and transforming her to Princess Serena/Serenity. The memories of their past love flood to them both. She faints. But Malachite appears and captures Tuxie and takes him to the Negaverse. There, his memory was erased, and he was turned evil to tend to Queen Beryl's, ...er....needs. She erased Darien's memory of the past and of being Tuxedo Mask, turning him into a warrior for the Negaverse."
This "new" Tuxie, raging with evil, chases after Sailor Moon for the Imperium Crystal. She is torn to see her love plot against her. She heals him once, but only for Queen Beryl to brainwash him again. In the battle with Queen Beryl, Saior Moon finds her dear Tuxie fighting against her. In dispair, she brings out the star locket, a symbol of their love. He touches it. The light flows through him and heals his soul. The red rose drops. He is free and once again he remembers his love for his princess. Out of jealousy and hatred, Queen Beryl throws a large crystal spear headed for Sailor Moon and Endymion. To save his love, he uses the last ounce of his strength to throw the final rose shattering the crystal. Sadly, a piece of the crystal found its way to Endymion and thus, putting a tragic end to dear Tuxie.....