Andy and Amanda (guest-star Anne Heche) decide that it's time to tell Delia and Charlie (guest-star Shane Haboucha) about their relationship before they hear about it elsewhere, but Charlie's emotional reaction makes them question what they're doing. Meanwhile, when Hannah (Sarah Drew) doesn't jump at the opportunity to go on a date with a really cute guy, Topher, from school, Amy is convinced that Hannah is misguidedly saving herself for Bright.

Nina questions whether Sam (guest-star Jimmy Bennett) is going to be hurt again if her relationship with Jake (Scott Wolf) doesn't work out. Lastly, we flashback to Amanda (Anne Heche) and John earlier in their marriage of a more happier time with their son Charlie, right before he has his stroke.

After returning from New York feeling lost and confused and needing Amy for support, Ephram considers his options in the wake of Madison's (Sarah Lancaster, who does not appear in this episode) life-altering revelation. Ephram tries to find the baby by going to Child Services Office, but finds out that Madison signed the adoption papers with "father unknown" and terminating the parent-child relationship with "Unknown Birth Father" leaving Ephram completely crushed.

Amy tries to get Ephram another audition at Julliard after he missed his first appointment due to the emergency with Madison and the baby, but it doesn't go well. Meanwhile, a tired Andy is a little stunned upon learning the extent of Nina's feelings for Jake and with a little encouragement from her friend Bright, Hannah decides to go on a date with a smitten Topher (guest-star Lukas Behnken).

An angry Ephram makes a bold move - and breaks his father's heart in the process - in an attempt to raise money for a plane ticket to Europe by selling his music equipment, except his piano, to "muscian" Jared and his band. Meanwhile, Nina can't quite put her finger on why Andy has been acting strangely of late, whereas a more perceptive Delia comes right out and asks her father whether he has feelings for Nina, and Bright's green-eyed monster makes an unexpected appearance when Hannah (Sarah Drew) goes to the prom with Topher (guest-star Lukas Behnken). Hannah becomes very upset when Bright insults her dress. Bright goes apartment hunting. Lastly, Rose begins her treatment at the hospital with Harold by her side.

Ephram prepares to leave for Europe as he feels that he has nothing left for him in Everwood. However, he's caught off-guard and questions his plans when Andy reveals the secret that Amy has been keeping from Ephram. Meanwhile, Nina and Jake contemplate going into business together, but the stress on their relationship proves a big obstacle to overcome. Meanwhile, Bright finally confesses he has feelings for Hannah.

With Ephram (Gregory Smith, who does not appear in the episode) gone and no longer feeling any significant ties to Everwood, Andy consults with Delia and contemplates accepting a prestigious position with a Chicago hospital. Uncharacteristically upset over this bit of news, Harold takes it upon himself to give Andy a reason to stay. Meanwhile, Jake moves in with Nina, causing Andy to question whether he should rock the boat by telling her how he really feels, and Bright finally admits his feelings to Hannah.

With Hannah leaving for Minnesota in a few days with her mother (guest star Jayne Brook, "Chicago Hope"), Bright and Amy find themselves taking the loss of their girlfriend and best friend, respectively, harder than even they expected. Jake sets out on a high-risk bike trip with his friend, Cliff (guest star Simon Rex), that takes a near fatal turn; Andy and Harold uncharacteristically decide to go skydiving after hearing of Jake's daredevil ways; and Reid (guest star Justin Baldoni) keeps his promise to Ephram and backs off from pursuing Amy, leaving her feeling all the more lonely.