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Ten years prior the Book 2 (three years before A Sim's Tale), Enrico was once Leona's neighbor in Twinbrook and had crush on her. Even though Leona was friend with his sister, Annie, but Leona apparently dislike Enrico's antics, she often called him weirdo. Despite this, it seemed that Leona was secretly admire and possibly also had crush on him.
Enrico and his family were moved out to the other town after one year living in Twinbrook. Leona gave her a handkerchief as a keepsake.
Ten years later, the Delgados moved in to Sunset Valley and reunited with their old friends, John and Lily Redfield, who came to help them unpacking their belongings.
In the next day during the weekend, Enrico was still asleep in his room when John and Leona came to made a visit. After Annie woke him up, Enrico greeted both the Redfields. Leona had her jaw dropped when seeing him for the first time after ten years and Enrico jokingly teased Leona by telling her that she slightly more feminine. Later, he and Leona were hanging out in Mirabello Plaza before went to Hogan's deep for dine.
Enrico later accompanied Leona in the gym until she went home. After saying goodbye, Enrico pedalled his bike quickly and didn't noticed that he dropped his handkerchief, which he still kept for ten years. Enrico's relationship with Leona became closer after he saved the girl from bullies.
Trivia
Enrico is fan of Queen with his favorite song is Bohemian Rhapsody.