Just rewatched the previous episode.:Molly's exact words were " I guess I can ask" , after Issa told her she found an Artist with roc nation and could she get ol boy to hook it up. A few hours later she hit her with the " I'm not gonna ask because I wanna keep those parts of my life separate ". She was in her feelings already about Issa joking with her at the friends house AND ol boy telling her at the dinner about him going to hangout with his boys to play poker. Add that in with them having underlying beef stewing , THAT was the real reason she didnt wanna help. ALL the debates and addons about going over people's heads is moot. MOLLY herself said she didnt wanna ask ,so boom Issa had the roommate ask( who called to reach out to her ) Issa wasnt wrong at all