Single mom Madison finds herself scraping pennies together two weeks before Christmas after the IRS freezes her bank account, her ex fails to come through with any help and her boss fires her. Desperate to pay bills and buy gifts for her teenage children, Madison jumps into the ever-popular "gig economy." That's when she meets and eventually gets hired by obnoxious, sidelined former pro football player Alec Darby, also secretly on the verge of going broke. This odd couple butts heads time and time again, but they eventually forge a friendship. And, to their surprise, they learn a lot about themselves and teach one another how to be better people.

Madison lands her dream job at a publishing company. To her dismay, she must complete a probationary period and will not receive her full salary until the process is over, leaving her in a financial struggle. With a new career and struggling to make ends meet, she works under the demands of her new job while raising two teens on her own. Making matters even more complicated, she finds herself torn between an old flame and a new love interest.

Madison and Alec are flourishing in their dream jobs and have grown their budding romance but new challenges open old wounds and threaten to derail their relationship and their friendship.