The holiday season is often painted as a time of joy, celebration, and togetherness. Images of families gathered around the dinner table, couples exchanging gifts, and friends laughing at holiday parties saturate our social media feeds, movies, and advertisements. However, for many, the holiday season can be one of the most challenging times of the year. This chapter delves into the phenomenon of seasonal loneliness, commonly referred to as the “holiday blues,” and explores the reasons why so many people feel isolated or depressed during a time when society expects them to be at their happiest.