Boy Meets Girl (1998)

Angelina (Emily Hampshire) is a shy and whimsical Italian waitress who has moved from Italy to Canada to fulfill a family vow by marrying a man she's not in love with. Angelina settles into a neighborhood in Toronto's Little Italy longing for true love. Mike (Sean Astin) is a jaded and cynical copywriter for romance novels but has lost his faith in romantic love. In the days leading up to Valentine's Day, an enigmatic and amorous couple named Il Magnifico (Joe Mantegna) and Mrs. Jones (Kate Nelligan) set the whole neighborhood ablaze with romantic passion. While everyone seems to be falling under the spell of Cupid's arrows, Angelina and Mike meet and just might find the true love that they've been searching for.