The 'Sad Will Smith' or 'Entanglement' meme originated from a July 2020 episode of 'Red Table Talk' featuring Will Smith and Jada Pinkett Smith. During the emotional conversation, Jada described her past relationship with singer August Alsina as an 'entanglement,' while Will appeared visibly distraught and glassy-eyed. Although Will later clarified that his expression was simply due to exhaustion and watery eyes, the internet immediately turned the still image into a symbol of heartbreak, regret, and the awkwardness of modern relationships. The meme is widely used to represent feelings of betrayal or when someone is forced to listen to a complicated explanation they didn't want to hear.