Trapped in a Dating Sim Season 2 Episode 1 starts with a battle as airships start destroying everything in the sky, while Olivia wonders whether the Saint's powers would prove to be enough. This is an audacious start to the new season as it brings the viewers into the fight before the story shifts to Leon's point of view.
This difference is what defines the episode. Trapped in a Dating Sim Season 2 Episode 1 depicts how Leon switches the chaos of the war for family drama and gets involved in protecting the self-proclaimed Saint. Then, he ends up on a treasure hunt he has never wished to take part in.
A Chaotic Battle Opens the Episode

The premiere features a war scene with fierce aerial battles. Olivia is uncertain of her power as the Saint, but Julius addresses her with confidence, saying that they will win. He immediately starts confessing his love, which is part of the sappy theme of this world.
Leon is watching the events unfold, unimpressed with everything happening around him. He points out how ridiculous the world is and its tendency to be governed by women. Leon’s grumbling about how crazy and sappy the whole premise of the story is runs throughout Trapped in a Dating Sim Season 2 Episode 1.
Family Drama in Trapped in a Dating Sim Season 2 Episode 1

Back home, Leon's family welcomes him with both pride and demands. Leon's father compliments him for being a noble now. Leon's brother wants to know about his dealings with the Redgrave family. As if this were not enough, Leon's sister expresses her indignation about the living conditions of her boyfriend.
Things escalate when Leon's mother comes looking for him. She tells him to give up the necklace Leon got from defeating the Sky Pirates. Leon is ready to refuse, but Luxion warns him that Temple warships are surrounding them. This leaves Leon no choice but to hand over the necklace, only to find out that Marie was behind it all and used a fake Holy Bracelet.
Marie's Rise and a New Alliance

Marie is pleased in her new role as self-styled Saint, while she silently looks down on the foolish boys who are devoted to her. Although she is annoyed by their adoration, she takes advantage of the opportunity to take poor girl Carla, who has been wrongfully accused of treason, under her wing.
Marie pretends to befriend treasonous Carla, but she only wants to use her later on. While this is going on, Leon is starting to question Marie’s motives behind her actions. Why has Marie changed her behavior so radically? This issue would imply that there would be more similar issues in the future in Trapped in a Dating Sim Season 2 Episode 1.
The Treasure Hunt Begins
Leon is named captain of the Saint's guard by the nobles who want him to fail. In spite of the political games, he decides to accept the role and goes with his team on an expedition towards a treasure island. Along the way, Princess Hertrude and Marie become antagonists, too.
Part of the sailing adventure is a bath scene, which is followed by a conversation between Leon and the princess. As the ship approaches the island, the elf girl informs Leon that she is familiar with her homeland, where they will land. And this is where Trapped in a Dating Sim Season 2 Episode 1 finishes.