Tear Jerker / Anything Goes

• After singing a whole song about how much she loves Billy, Reno gets rejected by him in favor of another girl, resulting in a fight that ends with him leaving and her singing a sad reprise of "I Get a Kick Out of You".
• Billy briefly starts to believe that he'll never have a chance with Hope. Luckily Reno raises his spirits.
• Despite loving him, Hope rejects Billy's first attempt at courtship. Her reprise of "Easy to Love" shows that she wishes they could be together, but she just can't find the strength to disobey her family duty.
• Reno's "The Reason You Suck" Speech to Hope. It's clear that there's a level of resentment there.
• After being chewed out by Reno, Hope bursts into tears, believing she's ruined both her life and Billy's as well. Fortunately, Billy shows up in time to sing "It's Delovely".
• Despite spending the previous night having a successfully romantic song and dance, Hope still can't go against her mother.
• After Billy starts acting like an ass, Hope runs away crying.
• Once Billy realizes how bad his behavior has been, he gives up the gangster persona and makes a heartfelt apology and promises never to speak to Hope again. This unfortunately gets him thrown in the brig.
• Evangeline pettily moves up the date of Hope and Evelyn's wedding as soon as she realizes she was an item with Billy. Hope finally objects to her mother but gets instantly shut down, causing her to sing "Goodbye Little Dream Goodbye".
• Much like Hope, Billy is at his absolute lowest, completely rebuffing Moonface's attempts to make him feel better and talking about a desire to shoot himself. Something that genuinely worries Moonface, whose attempts to cheer him up fall on completely deaf ears.
• While it's Played for Laughs, Hope saying that's there's no Hope despite admitting to loving Billy is still fairly sad.
• Billy and Hope singing "All Through the Night" where they declare their love to each other from a distance.
• Reno staying up drinking over her friends' failure. There's also the implication that she was already falling for Evelyn a bit and was saddened to see that she'll losing any chance with him at the same time Billy loses his chance with Hope.
• Evelyn himself is depressed, realizing that he's in love with Reno, but now has to go forward with a loveless Arranged Marriage. Much like Hope, as much as he wants to, he doesn't feel like he can go against his family, and starts to bid the woman he actually loves adieu. But then Reno starts to question him about his "romp in the rice".
• He may only be a minor character, and one that's fairly dated, but John ends up being thrown in jail because of Luke's actions, cries his eyes out, gets knocked out for trying to do the moral thing, and then gets his clothing stolen.
• Hope and Evelyn sadly walk out resigned to their fates as the wedding music plays. This isn't anything new for Hope who spends the whole show wangsting, but to see the usually happy Evelyn so depressed is jarring, especially since we last saw him during his epic, romantic tango.
• While they seems pretty pleased, Eli and Evangeline may wind up being pretty unhappy later on given she's only marrying him for his money. However, Eli's so content and blind to her bad nature and Evangeline will likely get along well with him so long as he stays rich, so they'll probably be fine.