University professor Madeline Walters isn’t doing too well in the dating game. Good men are hard to find, so she’s happy spending time with her Maltese puppy Cinnamon, and her precocious teenage daughter Chloe. But when she meets Kevin, a widower, the attraction is fast and mutual. The trouble is both Kevin’s son, thirteen year-old Jordan, and Madeline’s pooch Cinnamon are dead set against losing their parents in a romance. Little Cinnamon takes the lead and does her best to ruin the budding relationship between Madeline and Kevin, spoiling dates whenever she can. Until one day she is kidnapped by Sam, the boy who was bullying Jordan.