In "Clooney," Kevin leaves rehab and moves into Rebecca's home, where he directly confronts Miguel about whether he loved Rebecca while Jack was alive. Miguel's answer reframes the marriage entirely, and Kevin gives Rebecca permission to be happy. Randall retrieves William's belongings and follows a love poem and drawings to what he assumes is a secret romance, only to discover William's "Lady Day" was a Billie Holiday mural he watched from his apartment window every morning — which leads Randall to propose he and Beth buy the building together. Kate catches Madison purging at a bridal boutique, and when Madison later collapses and calls her, Kate opens up about her own history with disordered eating. A mall flashback shows a teenage Kevin advising Jack to let Miguel grieve, where Miguel reveals Jack once shelved a plan to start his own construct ...