When a retired high school teacher Eva loses her husband, she mistakenly receives a $5,000,000 check on her deceased husband's $50,000 life insurance policy. Her friend Maddie, whose husband has just left her for a younger woman, convinces her to keep the money and they both depart to live it up at a resort on Gran Canaria, in the Canary Islands. Once there, Eva is courted by an older gentleman who accompanies her in town. In the local casino she wins almost half a million euros despite knowing nothing about card games. Eva ends up in bed with him, enjoying lovemaking after a 7-year dry period with her husband. Her friend Maddie loses money, but finds a young, virile man who has just lost his girlfriend, and happens to like older women. Their sex rejuvenates her, but in the process he has strained his back. In the meantime, the American insurance investigator is on Eva's trail, together with her mostly estranged daughter, to get back the $5,000,000 for the Beneficial Life Insurance Company, but they are trumped by the Company's European representative who accepts a bribe to let her escape rather than sending her to the worst woman's prison in the Spanish-speaking world. Maddie realizes that the older gentleman is a scam artist, and with the hotel detective finds out that he's working for Don Carlos, the richest man on the island. Eva and Maddie escape from the insurance investigator and her daughter to go to Don Carlos, who is feared by everyone who knows him except his firecracker of a Brazilian second wife, who tears into him when his bodyguard, who is her lover and the father of her child, is disturbed by the guard's gratuitous gun fire. Besides cheating old women, Don Carlos also swindles wine snobs by selling them inferior wine with impressive labels from classy estates, though the bottles are occasionally dropped by the older gentleman, who is known under various names including Bix. The story ends on a happy note because Don Carlos gives Eva back her winnings: it turns out that Don Carlos was an exchange student in Liberty, IL, where Eva was everyone's favorite teacher, as has been said by various people who help her along during the movie. Maddie stays behind with her virile lover, while Eva goes back to the US where she ends up marrying the insurance investigator in a ceremony where all of the characters happily meet again.
On April 9, 2012, Dimension Films acquired the film, Howard Deutch was set to direct the film with Shirley MacLaine, Jacki Weaver and Alan Arkin joining the cast. On May 17, 2012, Jack Black joined the cast, but later dropped out. On October 17, 2013, Andy Tennant was announced to direct the film. On May 9, 2014, Jessica Lange and Sarah Jessica Parker joined the cast. On June 11, 2014, Demi Moore replaced Sarah Jessica Parker after she dropped out. On June 21, 2014, Matt Walsh joined the cast of the film.
Filming
began on June 10, 2014, in Gran Canaria, Canary Islands, and ended on July 15, 2014.
In February 2017, Impex Entertainment filed a lawsuit against Sony Pictures Worldwide Acquisitions for $1 million alleging failure to pay a $855,000 licensing fee no later than 10 days following the film's theatrical release, and an additional $95,000 payment, which Sony refused to pay. In March 2017, Sony followed a countersuit stating they failed to pay the fees after the film had premiered on Lifetime instead of in theaters, breaking the first public exhibition of the film contractual obligation.
