|Complete the Main Job “Double Life”
Both Sides, Now is the first Side Job in Judy’s questline - not to be confused with her Main Job questline, which ended with Double Life. It’ll begin after Double Life ends, after you’ve advanced the Main Job M’ap Tann Pelen by contacting - and hearing back from - Mr. Hands. After that just wait around, skip time or complete other jobs until Judy finally messages you, after which you’ll need to burn more time until Judy calls.
When you get the call head to Judy’s apartment to get an update on Evelyn’s status. Respond how you wish to Judy - it surprisingly doesn’t matter what you say - then carry Evelyn back to bed. When Judy’s done talking on the phone she’ll talk to you again. Again, respond how you wish, then leave and close the door behind you. After a time skip you’ll be on a roof with Judy, who will tell you about some recordings she found, the existence and substance of which both call for further action.
This will end the quest Both Sides, Now, which mostly just advances Judy’s storyline and transitions from the Main Jobs to the real focus of these Side Jobs. Wait a while (both real time and game time) and you’ll get a text from Judy about Evelyn, after which you’ve got more waiting ahead. Skip time and eventually Judy will call you, starting the next Side Job in this questline: Ex-Factor.