Clare's husband, Danny, has kicked her out of their home for giving her brother Lucas their daughter Rae's college fund; but an old friend needs someone to take on his advice column Dear Sugar, and it might be what Clare needs.
Clare grapples with whether or not she wants to become Sugar as she reels from trouble at work and with Rae; in the past, young Clare and young Lucas must confront their grief at Frankie's funeral.
Danny and Clare try to untangle their relationship and Rae's threesome, as Clare considers her path not taken; in the past, young Clare finds out she's pregnant with Rae.
As Clare deals with her Tik-Tok-famous Montana confrontation and Rae's recent partying, she's haunted by a letter writer who desperately needs Sugar's advice; in the past, young Clare learns of Frankie's diagnosis and desperately tries to save her.
A furious Rae tells Clare and Danny that she doesn't want to go back to her school; Clare remembers her college experience with Frankie and why she never got her degree.
Danny and Clare take a good look at their sex life as a letter writer writes about her boyfriend's secret shame; Rae grapples with letting Montana back into her life as she realises she might have the upper hand.
Kathryn Hahn
Clare Kinkade
Quentin Plair
Danny Kinkade
Sarah Pidgeon
Young Clare
Tanzyn Crawford
Rae Kincade
Merritt Wever
Frankie Pierce
