Advice columnist, Dan Burns is an expert on relationships, but somehow struggles to succeed as a brother, a son and a single parent to three precocious daughters. Things get even more complicated when Dan finds out that the woman he falls in love with is actually his brother's new girlfriend.
When notorious womanizer Connor Mead attends his brother Paul's wedding, he is forced to re-evaluate his behavior as he comes face-to-face with the ghosts of girlfriends past, present, and future, along with his deceased uncle. The experience changes his attitude and allows him to reconnect with his first and only love, Jenny.
Samantha Kingston has everything. Then, everything changes. After one fateful night, she wakes up with no future at all. Trapped into reliving the same day over and over, she begins to question just how perfect her life really was.