It makes sense that Gilbert's route, and by extension the Finale route, would be the route where an Enemy Mine situation would occur, forcing the Mafia groups to work together. The Visconti are all about taking in anyone with skills, even from other countries, and having everyone working together.
In order to complete the Best Ending for each love interest, each love interest has a different secondary attribute that the player must also score high on, each attribute that fits the characters when delving into it.
Dante's is Respect. He is the youngest out of the Mafia Bosses and someone who worked hard to get to where he is now. Due to his youth, he is often disrespected by the other Mafia bosses or even from senior members of the Falzone family and Dante himself struggles with making decisions for the Family that he as a person might not agree with. He responds best when Lili respects him both as a boss and as a person.
Yang's is Wisdom. Yang is easily bored, wants to be entertained and enjoys nothing but a thrilling challenge. Yang responds better when dealing with intelligent people or someone who doesn't simply bow down to his whims. Lili being smart and quick in her words and choices will both amuse and charm Yang, who likes that Lili can be unpredictable compared to people that Yang normally interacts with.
Nicola's is Honesty. He is a womanizer who can easily sweet-talk others and lie with a cheerful smile on his face. In his line of work, he has to hide his true feelings and thoughts. He even lies to Dante, the person who knows him the best. Answering Nicola honesty will throw him off balance and makes him realize that he cannot lie about his own feelings for Lili.
Orlok's is Tolerance. Orlok is very innocent and naïve about the world and how not everything is as black and white as to what the Church tells him. Being honest or straightforward with him will be detrimental as he can take things too literally and he is very strict with himself in his role to protect Lili. Being kind and patient with Orlok helps him to slowly realize his feelings for Lili and learn to be human.
Gilbert's is Trust. While Gilbert seems to get along with everyone, he doesn't actually reveal much about himself or his past. In his route, he loses the trust of many townsfolk which does bother him even if he doesn't show it. Lili explicitly trusting him and staying by his side no matter what allows Gilbert to feel comfortable with Lili and be himself.
