Meeting her at the mission he offers her dinner in Havana in return for twelve genuine sinners to boost her flailing mission that is threatened with closure. He tells her that “I’ll Know” when he falls in love, kissing her and getting slapped. Nathan visits the Hot Box nightclub to watch his long suffering fiance of 14 years Adelaide (Michelle Walker) perform with her girls (“A Bushel and a Peck”). She asks him when will they be getting married and is angry that Nathan is still involved with gambling. She consults a medical book that tells her her constant cold is brought on by her need to be married, (“Adelaide’s Lament”).
The boys watch Sky continue to pester Sarah, noting that guys will do anything for the girls they love, (“Guys and Dolls”). Sarah is put under pressure by General Cartwright (Janet Reuteler) who demands that they bring in more sinners to the mission. Sarah promises 12 genuine sinners,, implicitly agreeing to Sky’s bet. Nathan watches the mission parade past the town, after he has agreed to elope with Adelaide and faints when he sees Sarah isn’t with them meaning he has lost his bet.
In Havana, Sky treats Sarah to a fun evening, and she drinks cocktails without knowing they are alcoholic. She kisses Sky and feels happy for the first time, (“If I Were a Bell”) and Sky realizes he does have feelings for her. He takes her back to New York and on the street admits that “I’ve Never Been in Love Before”. As the police siren sounds, the gamblers run out of the mission where Nathan has been holding the crap grame. Sarah assumes Sky only took her to Havana to get her out of the way of gambling activities and she leaves angrily.
Adelaide continues to perform at the Hot Box (“Take Back Your Mink”) and as Nathan doesn’t show up for their elopement she consults her book again, (“Adelaide’s Second Lament”). At the Mission Sarah confesses that she is in love with Sky but can’t forgive him for fooling her. Her urges Sarah to follow her heart (“More I Cannot Wish You”). Sky arrives and promises her the sinners for the mission but she ignores him.
Nathan directs Sky to the sewers where the crap game is underway. Sky bets every sinner $1,000 against their souls, saying if they loose they have to attend the mission for him, (“Luck Be a Lady”). Sky wins and the sinners head towards the revival meeting. Adelaide stops Nathan and asks how much more she has to take (“Sue Me”) but he convinces her that he love her.
Everyone arrives at the mission and Nicely invents a story to get everyone confessing, “Sit Down You’re Rocking the Boat”. The police arrive and Sarah steps in to save them all, providing them with an alibi. Nathan confesses to her that it was he who arranged the bet with Sky and that Sky has only ever looked out for her feelings. Sarah runs into Adelaide and they share tips about resolving their pre-marital problems, “Marry the Man Today”. Some time later, Nathan prepares to marry Adelaide at the mission, just as Sky and Sarah have been married and Sky leads the mission band.