Midge and Rose begin planning for Midge's future as Benjamin attempts to impress Abe. Joel stresses over his next move, while Abe is presented with some big decisions of his own. Meanwhile, Susie tries to smooth things over for Midge.
Rose visits her psychic who "sees" Midge in front of a large audience, which Rose assumes is a wedding. A flashback shows Joel proposing to Midge (without first asking her father for permission). Meanwhile, Benjamin asks for Abe's permission to marry Midge, despite her still being married to Joel. Abe requires that Ben provide relatively intrusive personal details before deciding.
Abe wants to quit Bell Labs and Columbia University to return to social activism. Sophie Lennon wants Susie to become her manager, saying no one fights for her the way Susie does for Midge. After seeing Midge perform, singing star Shy Baldwin asks her to open his six-month tour in the US and Europe; she immediately accepts.
After being pulled offstage for discussing pregnancy, a dejected Midge encounters Lenny Bruce in a bar. Lenny, equally dejected and nearly broke, says his wife has left him and there are arrest warrants out for him (for obscene language in his act). Midge goes with Lenny when he performs on Steve Allen's TV show, but his "All Alone" routine incites fears that she will end up successful but alone.
Meanwhile, Abe gives his approval for Midge and Benjamin to marry. Midge goes to see Joel after Lenny's show, saying she needs to spend the night with someone who loves her.
- “Shall We Dance” performed by Gertrude Lawrence, from the Broadway soundtrack for The King and I (Joel proposes)
- "One for My Baby (And One More for the Road)" performed by Frank Sinatra (Midge and Lenny talk at the Dublin Room)