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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. 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 had crush on him.
Enrico and his family were moved out to the other town after one year living in Twinbrook.
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.