Holiday Heartbreak follows the story of a young woman named Maya, a hopeless romantic who dreams of finding her soulmate. Maya's father, George, is a successful lawyer who has instilled in her his old-fashioned values and beliefs about love and relationships. George is also a chauvinist who mistreats the women in his life, including his wife and Maya's mother.
One day, Maya meets a charming and handsome man named Devin, and they hit it off immediately. Maya is convinced that Devin is the one for her, but her father disapproves of their relationship and tries to convince her to break things off. George's chauvinistic views and behavior cause a rift between him and Maya, and they soon find themselves at odds.
Things take a turn for the worse when George mistreats Devin's sister, who happens to be a close friend of Maya's. This incurs Devin's wrath, and he decides to take revenge on George by making Maya fall in love with him even more deeply, only to ultimately break her heart.
As the holiday season begins, Maya tries to navigate the ups and downs of her relationship with Devin and deal with the fallout from her father's actions. Ultimately, she is forced to confront the realities of love and relationships, and must make some difficult decisions about her future.