After Jessie accepts an invitation for lunch with Tony, the building's doorman, Emma offers Jessie unsolicited dating advice she has learned from her stash of teen magazines. Meanwhile, Ravi becomes the target of Luke's practical jokes.

After a music producer spots Jessie singing a song she wrote, she is over the moon with excitement about the possibility that her big break has finally arrived. Meanwhile, Bertram enlists Emma to help style him for his social network profile photo.