We meet Clare as her 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 exactly 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. If Clare can't figure out her own life, can she be Sugar?

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.

When a furious Rae tells Clare and Danny that she doesn't want to go back to her school, Clare remembers her own college experience with Frankie - and the reason she never got her degree.

Danny and Clare take a good (ahem) hard look at their sex life as a letter writer writes in about her boyfriend's secret shame. Meanwhile, Rae grapples with letting Montana back into her life as she realizes she might just have the upper hand.

Clare and Amy attend a writer's retreat, but when Amy gets great news, Clare can't help but question if her sacrifices for Danny and their family have been holding her back. As she remembers her first marriage to Jess, she wonders: should she stay or go?

Fresh off shocking news from Danny, Rae reveals who really dropped off the missing money - causing Clare to bring Rae along on a mad dash road trip to Clare's childhood home. In the past, Clare rushes to get Lucas to the hospital for Frankie's last days.