Ally Simms is an "expert" on love, dispensing hard hitting advice on her radio talk show, Love Speak. Her advice is to look for a guy who is rich, smart, good-looking and ambitious. This is what Ally has in her fiance Matt, a successful attorney she plans to marry on Valetine's Day. But as her wedding day approaches it is Ally who needs a lesson in love and who better to guide her than her recently deceased mentor, Jackie Marley. Jackie is stuck in Heaven's parking lot and must help Ally to earn her place in Heaven. Ally will go on a voyage to her past, present and future to learn true love before it is too late.