For some, a bet is a game. For others, a simple, friendly wager becomes the catalyst for facing their fears and admitting their desires. When Jess Halliwell extends a playful bet to her friends, she has no idea what she's in for.
After yet another breakup, Jess has resigned herself to never finding a woman to settle down and raise a family with. Content to live vicariously through her sister, Jess spends as much time as she can with her nephews. After a chance encounter with her sister's friend at the park, Jess starts to question her choice of women. She's had no luck with her typical type of partner, and meeting Karli Adams, a beautiful redhead with a wife who offers almost no help with the raising of their six children, makes Jess once again long for a family of her own.
When Jess sees for herself how little help her sister and new friend receive from their spouses, she decides to offer them a bet. Spend one whole day in their wives' shoes, and receive free babysitting for a year. Little did she know that, in trying to prove a point to her friends, she would set herself on a collision course with fate. Will Jess find the woman she longs for? Or will her own fear of the past prevent her from the family she's always wanted?