After Clare is kicked out of her home by her husband Danny for giving her brother Lucas their daughter Rae's college fund, an old friend needs someone to take on his advice column Dear Sugar. And it might be exactly what Clare needs.

Clare grapples with whether she wants to be Sugar while reeling 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 the path she could've taken. In the past, Young Clare learns she's pregnant with Rae.

While dealing with her viral Montana confrontation and Rae's recent partying, Clare is haunted by a letter writer in need of Sugar's advice. In the past, Young Clare learns of Frankie's diagnosis and tries to save her.

A furious Rae tells Clare and Danny she doesn't want to go back to school, prompting Clare to remember her own college experience - and why she never got her degree.

Clare and Danny take a good look at their sex life as a letter writer describes her boyfriend's secret shame. In the meantime, Rae grapples with letting Montana back in her life as she discovers she may have the upper hand.

Clare and Amy attend a writer's retreat where Amy receives great news and Clare wonders if her sacrifices for her family are holding her back as she remembers her first marriage to Jess.

After Danny delivers shocking news, Rae reveals who dropped off the missing money - leading Clare to bring her on a road trip to Clare's childhood home. In the past, Clare races to get Lucas to the hospital for Frankie's last days.