We meet Nicky, Charlie, Pepper, Heidi and Alan, five post-grads living in Manhattan, who tell us who they are and what they do (I SING!). Confronting their whole future, they all express a desire find love and happiness. Nicky is scared that he will end up bitter like his parents, but says, "I WON'T LET IT HAPPEN TO ME," and vows to get everything he wants.
We go to Nicky and Heidi's apartment, where we find their best friend Alan living on their couch. Alan complains that they are not the PERFECT PAIR of lovers they claim to be. Heidi shares a typical late night phone call with her father, reminding him that she will always be his DADDY'S GIRL.
Across town, Pepper and her gay roommate Charlie are getting ready for a night out. Pepper tells Charlie, "You're MY FAVORITE GUY," as they tease each other and she flirts with him. Charlie reveals to us that he is attracted to Pepper and confused about his sexuality.
Waiting to meet Heidi at a bar, Nicky laments about his relationship troubles to the bartender Pepper, asking "HOW DO YOU LOVE A GIRL LIKE THAT?" When Heidi arrives, A NIGHT AT THE BAR turns into a break-up for her and Nicky. After Heidi leaves, Pepper seduces Nicky.
At the same time, alone in his best friend's apartment, we learn WHAT ALAN LIKES; he likes Heidi.
Later that night, Charlie is gearing up to tell Pepper he's in love with her (I'M COMING OUT). Soon, he discovers that Nicky and Pepper have just slept together. Nicky and Pepper agree to keep their romance hot (PROMISE ME), while Charlie is left out, his plans ruined.
Alan accompanies Heidi to buy a sexy dress in order to win Nicky back, but ends up falling for her harder (THE DRESSING ROOM SHUFFLE).
Charlie and Pepper play DRINKING GAMES alone in their apartment as he works up the courage to express his true feelings for her. When he finally does, she rejects him and he leaves, embarrassed.
Heidi, fearing that Nicky may not come back, reflects on the memories they shared together in THE OLD APARTMENT, and goes through the reasons she still wants to be with him.
Nicky confides in Alan that he may want to get back together with Heidi. Alan reveals that he, too, wants to date Heidi, causing Nicky to leave in a rage. Alan makes a move on Heidi, leaving her confused. Pepper and Nicky get in their first fight. Charlie feels lost in the shuffle. As ALL THE CHILDREN SING, everyone is left hanging by the person they most want.
Two weeks later, things in the bedroom have become a little AWKWARD. Heidi and Alan are having bad sex, Nicky and Pepper are have weird sex, and Charlie is having no sex. Alan begs for more out of the relationship when he asks, "HEIDI ARE YOU THERE?"
Charlie plays MORE DRINKING GAMES as he interrogates Nicky and outlines an elaborate plan for the two of them to date Pepper together. Pepper interrupts with bad news from Alan: Heidi's father has had a heart attack. Nicky runs out on Pepper for the hospital, and Pepper and Charlie get in a fight in which he stops speaking to her.
At the hospital, Heidi opens up to Alan that she has always felt like her DADDY'S GIRL, and that she is terrified of being without him. Nicky never shows up.
Charlie and Alan bump into each other in Central Park and realize they were childhood friends at summer camp. They reenact a camp vaudeville routine as they remember their old motto: "You've got to SMILE THROUGH THE PAIN."
When Nicky and Pepper meet again, he tries to break up with her, but she beats him to the punch. Devastated, Pepper discovers a fatal flaw in her dating habits and decides she is STARTING OVER. Feeling clear-headed, Charlie admits he is just desperately lonely and not in love with Pepper after all. PEPPER AND CHARLIE reconcile and vow to take care of each other forever.
NICKY RETURNS to his old apartment to win Heidi back. Alan informs him he is too late and berates him for never having been GOOD ENOUGH to her. Desperate, Nicky begs Heidi to take him back, but she rebukes him. She wails, YOU SAID YOU LOVED ME, and she tells him that she realizes none of it was true.
Nicky is left by himself, forced to confront that he is DANCING ALONE. Just as he is ready to bitterly abandon everything he wanted, he has an epiphany that growing up means finding peace in not getting everything you want. He and his friends are ready to make a fresh start (FINALE).