Allison Williams, a young female attorney, tries to impress her law firm partners in an attempt to make partner with her first big case, but she is jeopardized by the opposing attorney, Derrick Walker, who has been a real jerk in their phone calls and emails . When she meets a really nice guy in her neighborhood and then later connects with him at a destination wedding, she starts to have strong feelings for him, but she will later discover that he is the opposing attorney on this important case. Will love prevail?

The story of New York lawyer Hugo who heads to Milwaukee with his best friend Madelyn to spend the holidays with his mom Kate, who is also in charge of the local Christmas celebrations. Ever the matchmaker, Kate arranges for Hugo to run into Patrick, Hugo’s high school friend and secret crush, who has recently returned after a successful stint in Silicon Valley. As they enjoy the local holiday festivities together, Hugo and Patrick’s attraction to each other is undeniable and it looks as though Kate’s Santa-style matchmaking is a success. But as Hugo receives word of a big promotion requiring a move to London, he must decide what is most important to him.