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A man learns about life and love from someone who has only so much of each to spare in this romantic comedy-drama. Jack (Freddie Prinze Jr.) is an advertising executive in his early Thirties who has grown jaded before his time; he devotes his life to his work but doesn't believe in it, and is trapped in a cycle of habits and routines. One day, Jack meets Jill (Taryn Manning), a beautiful young woman who clearly has no idea how to get around New York; Jack helps give her directions and is soon taken by her charm and enthusiasm for life, even if he's too cynical to share her sunny optimism. Learning that Jill needs a place to stay, Jack offers to let her stay at his place, and while the arrangement is meant to be platonic, it doesn't take long for a romance to blossom between them. Jill encourages them to develop a manifesto for responsible and compassionate living and Jack's heart begins to open up, but when Jill begins disappearing in the evenings he suspects that something is wrong. While Jack imagines at first that Jill's met someone else, the truth is more serious -- she's living with cystic fibrosis and despite regular treatments has only so much time left. Jack and Jill Vs. The World was written, produced and directed by Vanessa Parise, who also appears in the supporting cast with Robert Forster and Charles Martin Smith.