Billy and Julie come up with an entrepreneurial scheme to sell bottled library water-fountain water and Julie gets in trouble for a controversial tweet.

Julie seeks out an old high-school crush, and brings him to bed with her and Arthur. Meanwhile, Billy finds a father-figure in Denise's husband, Nate.

When their frequent trash-talking of celebs gets them kicked off Bravo, Billy decides to be nice, which fails at drag bingo. Billy meets Fred, a nice dentist, who volunteers at performances -- a deal breaker. Arthur, dealing with the PBS pledge drive stress, and Julie fight. Julie comes to the pledge drive to support him, but her trash talk causes his big guest, Marc Shaiman, to leave. In an effort to salvage the pledge break, Julie and Billy do an impromptu roast to PBS stars, which becomes a successful viral video. In an effort to win Fred back, Billy goes on stage at an Abra Cadouglas show, a 12-step magician, causing Fred to realize what a turn-off participation is.

Billy visits his very Jewish brother for Yom Kippur dinner and Julie attempts to befriend a veteran to prove to Marilyn's surrogate daughter that she’s charitable.

When Julie and Billy find themselves watching videos of younglings much more successful than themselves, they decide to do something about it. Julie attends an event put on by Marilyn, and learns Chrissy, the girl she used to babysit, has had tremendous success on YouTube. Meanwhile, Billy learns he might have a shot at appearing on SNL. While the two strive to be stars both online and on the TV screen, they manage to reinvent the café Billy is working at into a successful restaurant called "The Children’s Menu." When their plans for fame fail, Julie and Billy find themselves ridiculed on Chrissy’s channel and watching a SNL episode featuring, young adults.

Billy and Julie meet with Robert Spooner, a potential manager who wants to take their writing packet to a late show in 24 hours. Julie period is also late. Instead of writing, Billy and Julie attempt to buy a Ping-Pong table from Charles Grodin, watch old shows at the Paley Center, and tour Wendy Wasserstein’s old apartment. Julie and Billy write all night long, earning them a meeting with the head writer, Adam Balk. But in the interview, they learn that Adam didn’t read it and just wants a diversity hire. Julie and Billy dramatically say no to Adam. Robert, impressed, signs Billy and Julie, who happily gets her period.