S1, E1: New York lawyer Hugo (Ben Lewis) heads to Milwaukee with his best friend Madelyn (Ellen Wong) to spend the holidays with his brother Aiden (Chad Connell) and his mom Kate (Fran Drescher), who is also in charge of the local Christmas celebrations. Ever the matchmaker, Kate arranges for Hugo to run into Patrick (Blake Lee), 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.