Jimmy and Karen are lost in love after finally sharing a night together, but the romantic feelings are quickly squashed in the morning when her father, Roger, knocks on her door, a surprise visit. Jimmy sneaks out the fire escape, but Karen's father notices someone in a leather jacket sneaking off. Ivy ignores her mother's fifth phone call of the morning as she walks to rehearsals with Sam. Outside, Linda stops Ivy to tell her Tom and Eileen need to speak with her immediately - in private. It sounds ominous.
Julia is still caught up in her fallout with Scott as she tries to structure a proper apology email at work. As Tom tells her to relax, Linda announces Ivy's arrived, prompting Tom to freak out. Julia's stunned - why didn't Tom tell Ivy yet!? Luckily, Eileen steps in to drop the bombshell: they've cast Ivy's mother Leigh Conroy in the role of Gladys, Marilyn's mother. Ivy is mortified! Leigh hasn't officially accepted the role, as she's waiting for her daughter's blessing. But Eileen makes it clear the show needs Leigh to boost the business side of the show. Ivy doesn't really have a choice.
Derek walks into rehearsal and stops Karen as she sings "Broadway Here I Come" - they have a lot of preparing to do if they're going to be ready for the big fundraiser that night. Scott lets everyone know tonight is the show's first introduction to the patrons and board members of the theater, so they have to make a splash; he wants Ana, their diva, to perform as well. Jimmy is late to rehearsals because he "overslept," and as he's talking on the phone with Kyle, he sees Adam the drug dealer. Jimmy takes off in the other direction hoping not to be seen. Karen pleads with her dad to stay for the rest of rehearsal; she wants him to see why she left "Bombshell," and he's not sure he does.
At "Bombshell" rehearsals, Tom tries to apologize to Ivy before her first practice with her mom, but she's not having it. Contrary to expectation, Ivy and Leigh perform like two treacly soap actresses during rehearsal, despite the fact they're acting in a contentious scene. Tom tries to get behind the choices of each actress, but can't seem to identify the wall between mother and daughter. Eileen calls Richard at the New York Times, asking him to come for his feature tomorrow instead. They'll be ready then. Eileen flirtatiously promises to pay him back with dinner next week, and Richard seems more than willing to accept. Is it a date? Of course not - that would be a conflict of interest...
Derek tells Karen not to worry about her father's apprehension towards "Hit List" - both she and Derek took risks with this show, and only time will tell if it pays off. He suggests she bring her father to the fundraiser that night so he can see for himself. When Jimmy finally does show up for rehearsal, Derek gives him a hard time for his truancy. Karen tries to talk to Jimmy about what happened between them the night before, but both are awkward and vague when it comes to defining it's meaning, as they stumble over words and say things that get misinterpreted - like, Jimmy asks Karen to keep whatever's happening between them private. Suddenly, Adam the drug dealer shows up. Jimmy takes the conversation outside, leaving Karen high and dry.
Adam confronts Jimmy about the money he owes him. Jimmy's got his name all over posters outside the theater, so surely he has enough to pay his debt to Adam. But Jimmy, literally backed against a wall, explains he doesn't have the money right now. Adam promises Jimmy he'll be seeing more of him. Meanwhile, Derek asks Roger to attend the fundraiser so his daughter can show him why she left "Bombshell." Noticing Derek's leather jacket, Roger treats him with protective skepticism, but agrees to attend the fundraiser that night.
Back at "Bombshell" rehearsals, Leigh accidentally reveals to Sam that Tom was the one who begged her to join the cast... though it was Eileen's decision. Eileen asks Julia if she'd like to attend the fundraiser for "Hit List" that night to see what Karen and Derek are up to. Julia agrees, knowing it's a chance to see Scott. During rehearsal, Tom tries to coax personal experiences out of Leigh and Ivy's real relationship for performance motivation, but the exercise backfires big time. Both share unflattering stories, until Ivy reveals she's spent a lifetime being told she's not good enough. Ivy belongs on "Bombshell"; Leigh doesn't. But at least she's got a career ahead of her, while Leigh's is almost over.
Karen sings "Broadway Here I Come" at the fundraiser that night while Derek and Roger look on. Roger blames Derek for Karen's departure from Broadway, though Derek makes it clear Karen's decision was completely her own. Roger's read about Derek and knows his unsavory reputation. A real man would take responsibility... while a boy would escape out the window. Derek is rightfully confused. Jimmy asks Scott for an advance on his pay, but Scott says he can't do that, as they're a non-profit theater company, and it's pretty much hand to mouth. When Jimmy leaves, Scott and Julia run into each other. Julia lets him know she still feels terrible, but Scott's already picked up on that and kind of enjoying it. Tom shows up, delighted to find that Eileen has arranged for him to sit at her table - the flirtation is on!
Backstage, Ana is dressing for her performance, when Kyle tells her Richard Francis from the New York Times just arrived. Karen wonders where Jimmy is, and everyone agrees he's been acting weird all day. A nervous Ana is called on stage to perform "Reach for Me." Her act is a mesmerizing aerial number, with dancers hanging from silk over the audience. As her performance captures the imagination of the crowd - and Richard - Jimmy sneaks into the coat check and starts ransacking coats for valuables. Jimmy finds a nice watch in a coat, but Derek notices him and calls his name. Jimmy's caught.
Jimmy comes clean to Derek. He's in trouble. He took $8,000 from Adam a year ago in order to start a new life and get out of the drug scene. But now Adam's come looking for the money. Derek wonders why Jimmy didn't just come to him in the first place, confusing Jimmy. Derek's kidding, right? Actually, he's not; Derek thought he and Jimmy were becoming friends. Jimmy and Derek grab their coats. Back inside the fundraiser, Julia tells Scott she's comforted by the fact that her betrayal led him to this fantastic production. He's doing fine without her. With the ice finally broken, Scott tells Julia he hopes to see her around more.
Derek introduces Jimmy to Roger, who immediately realizes both Derek and Jimmy are wearing similar leather coats. Karen walks her father outside to catch a cab as Richard from the New York Times introduces himself to Scott and commends him on the preview. If The Diva is a big part of the show, he can't wait to see more. After Richard leaves, Derek and the creative team conspire to ramp up Ana's role in the musical. Alone, Richard tells Eileen he wants to see more of her, on a personal level, and lets her know he's giving the "Bombshell" story to another writer so there's no conflict of interest.
Back at "Bombshell" rehearsal, Leigh apologizes to Ivy, who's not going to return the favor. Ivy resents Leigh for accepting the role of Gladys. Leigh knows "Bombshell" needs her to open the show. This may well be true, but after the show opens, Ivy will never need Leigh again. Outside the fundraiser, Roger tells Karen he knows why she left Broadway: it's Jimmy. Karen tells him she really cares about Jimmy, and "Bombshell" is a part of her past now. If "Hit List" is a mistake, well then, she already made it. Roger leaves, agreeing with her final statement.
The next morning at rehearsal, Ivy and her mother Leigh finally put their personal qualms behind them to focus on the show. They perform the duet "Hang the Moon," and it's exactly what Tom imagined - there's not a dry eye in the house. In a way, the performance connects mother and daughter on an emotional level they hadn't experienced in a long time. This onstage partnership might work after all. Elsewhere, Derek gives Jimmy the money he needs to clear his debt with Adam. On his way out, Jimmy runs into Karen and Roger outside the theater. Roger's had a change of heart about Karen's decision and asks Jimmy if he'll join them for dinner. Roger apologizes to Derek, explaining he mistook him for Jimmy and thought he was seeing Karen. Finally clued in, Derek has a new regard for Karen and Jimmy: envy.
Jimmy apologizes for his weird behavior as of late, but promises he's better now. He doesn't say it, but Derek's generosity has lifted a monkey off his back. Meanwhile, Julia meets Scott for coffee. Scott offers her the chance to make up for the pain she's caused him by helping with the "Hit List" book. It would have to be in secret, since Derek doesn't know about it, but Scott trusts Julia to tighten the script. She agrees. Despite her amazing performance in rehearsal, Ivy still resents Tom for hiring Leigh; he knew he was effectively forcing her back into the shadow she's spent her whole life trying to escape Tom claims he was just doing what was right for the show. Ivy says she'll do the same, but they're no longer friends. Tom is just her director now.
Jimmy repays his $8,000 debt and tells Adam he never wants to see him again. But before he goes, Adam offers Jimmy some drugs as a gesture of gratitude. Jimmy's worked so hard to start his life over, but the temptation is too much to turn down. He reluctantly takes the drugs and walks away, as Adam calls after him. Jimmy's secret is safe with Adam...