When Penny Knightheart moves back to Miami, she knows she'll be thrust back into the drama that used to be her life. With a gold-digging mother clamoring for anything she can get her hands on and friends with a flair for drama, it's all Penny can do to not get sucked back into it, but they're the least of her problems when she runs into Jay Marshall, her former crush who kept her firmly in the friends' zone for years. No one is happier to see Penny than Jay. No sooner does she arrive when he sets a plan in motion. His investors need reassurance that he can keep a stable relationship with a relatively stable woman. No one fits the bill better than the ever-loyal Penny. There's just one hitch - after reuniting with her, he finds himself wanting her more and more. That definitely wasn't part of his plan. Soon, a pretend date sets off a whirlwind of trouble. From mothers who want full control of their children's lives to the loss of Penny's new job and obstacles neither Penny nor Jay could have seen coming. On top of that, she just might be falling for Jay all over again. Can these longtime friends build a lasting relationship from scratch? Will their full-proof plan lead to disaster?