After losing the woman of his dreams, Anderson is convinced he'll never fall in love again. But at the urging of his best friend, he spontaneously proposes to a dissatisfied waitress named Katie and an innocent dare evolves into the kind of love that both have been looking for all along.
On the brink of losing her childhood home, Maddie discovers an intriguing job listing: wealthy helicopter parents looking for someone to “date” their introverted 19-year-old son, Percy, before he leaves for college. To her surprise, Maddie soon discovers the awkward Percy is no sure thing.
A lonely doctor who once occupied an unusual lakeside home begins exchanging love letters with its former resident, a frustrated architect. They must try to unravel the mystery behind their extraordinary romance before it's too late.