Jenna Lakes has always been the smart, collected, and cynical older sister...and the complete opposite of her little sister - the bubbly, sweet and caring advice-columnist, Leanne Lakes. When Leanne leaves for a three-month honeymoon with the love of both sisters' lives, Jenna finds herself struggling with her private heartbreak as she fills in as "Jaime," the gender-neutral name her sister uses for her wildly popular advice column. There's just one problem - readers of the "Dear Jaime" column have come to expect compassion, sweetness, and, in Jenna's opinion, "puke-inducing froofiness." And Jenna has no intention of continuing that for three months. As her unusual Dear Jaime responses begin to gain public attention, Jenna must decide what she wants: she can either choose to stay safe by pushing away chances of friendship in the workplace and chances of love in the form of the easy-to-look-at Kenneth Owens... or, possibly, choose to follow her own advice and live fearlessly and fully.