In the second season opener, the town of Everwood deals with the aftermath of Colin's unsuccessful surgery, as he is now dead. The Brown family begins to feel ostracized by the town due to Colin's death. Meanwhile, a saddened Andy feels guilty of not doing his very best as regretting now over his promise to Colin of not resuscitating him if the surgery goes wrong. Amy and the rest of the town find out about this matter and confront Dr. Brown over it.

When Andy invites Linda Abbott over for dinner to discuss a patient, Delia lashes out through foul language, but it is an enlightened Ephram who figures out the cause of his sister's bad behavior, thanks to insight provided by Madison (Sarah Lancaster). Amy's depression deepens, but when her therapist recommends medication, Dr. Abbott refuses to write a prescription to help his daughter cope with Colin's death.

Dr. Abbott suspects that Linda and Andy like each other more than they should, so he decides to set his sister up with more appropriate suitors. Meanwhile, Ephram finally has the courage to tell Amy how he really feels about their relationship, but he is confused by his feelings for Madison, who comes to the rescue when Ephram needs help to pass his driving test. Meanwhile, Andy tries to help the soon-to-be-remarried Reverend Keyes (guest-star Tim DeKay) cope with his impending blindness, but the minister would rather leave his fate to God than attempt a new treatment that might save his sight.

Dr. Brown courts Linda Abbott despite Edna's and Harold's insistence that he's wasting his time, but Andy persists, forcing Linda to tell him that she is H.I.V. positive. Bright tells Ephram he can win Madison's affections by ignoring her, but the plan goes awry when she breaks up with her boyfriend. Amy meets a flirtatious and attractive town bad-boy, Tommy Callahan (guest star Paul Wasilewski), whose compassion for her problems touches her heart for the first time since Colin's death.

Ephram is horrified and heartbroken after he impulsively tells Madison (guest-star Sarah Lancaster) that he loves her and she doesn't reciprocate. Meanwhile, Linda naively agrees to watch Delia overnight so that Andy can accompany Ephram and his piano teacher, Will (guest-star James Earl Jones), to a jazz competition in Boulder, and Amy breaks up with Tommy (guest-star Paul Wasilewski) after realizing she might not be able to trust him again.

Amy confides to Bright that she may have developed feelings for Ephram and sees him in a new light, but Bright begs her to have mercy on poor Ephram, who is still nursing a broken heart from his recent break-up with Madison. Meanwhile, Linda reveals her HIV status to Delia after the girl confronts her about all the pills she's been taking. While Delia takes the news better than expected, the rest of the town goes ballistic after Linda's secret unintentionally becomes public knowledge. Dr. Abbott faces a potential malpractice suit, and Andy is forced to come clean with Ephram, who doesn't take the news very well.

Ephram and Amy are reunited after a long summer spent apart while Ephram attended Julliard's summer program in New York, but Amy's euphoria is quickly replaced with paranoia after she notices Ephram acting distant. Meanwhile, Andy is plagued by guilt over whether he made the right decision concerning Madison's pregnancy, and Dr. Abbott befriends the town's newest citizen, Jake Hartman, who turns out to be a doctor from California looking to open a new practice in Everwood.

Andy finds himself at a loss over what to do when Delia naively stumbles upon Nina's vibrator and starts asking questions. Meanwhile, Ephram attempts to write Amy a love letter to show her the extent of his feelings. Amy makes it her mission to make new best friend Hannah (Sarah Drew) popular. Meanwhile, Harold and Rose question Bright's euphoria over being selected "employee of the month" and decide it's time for some parental intervention.

Dr. Abbott becomes worried that his son Bright is settling too little in life when taking a job at a restaurant. Lastly, Andy treats a patient who needs a transplant, but won't tell his wife.

Andy puts his foot in his mouth by picking a fight with Everwood's patron saint, Amanda Hayes (Anne Heche), who, unbeknownst to Andy, has been caring for her profoundly disabled husband (guest-star Jason Beghe) for the past five years. Meanwhile, Jake surprises Nina by asking her out on a date; Ephram and Bright realize their friendship may have grown too far apart to salvage; and neurotic-as-ever Dr. Abbott struggles to come up with a medical invention after learning that Dr. Brown and Dr. Hartman have successful inventions of their own.

Amy and Ephram decide to meet at the Abbotts' Cabin to take their relationship to the next step as both parents on each side worry as they know their kids intentions. Although while there they realize they may not be able to handle it. Andy and Amanda chaperone Delia and Charlie on a date. Although the evening turns when Andy and Amanda begin to feel they are on a date. Lastly, Nina turns to Jake when Sam is hurt while ice skating and her feelings for him change.

Just as they've become somewhat comfortable with their new relationship, Andy and Amanda receive word that Amanda's husband, John (guest star Jason Beghe), has experienced a miraculous breakthrough in his recovery. Meanwhile, Amy learns the truth about why Madison really left town, an elated Ephram is offered an audition at Julliard, Hannah questions whether she's emotionally prepared to take the test for Huntington's Disease, and Bright is accused of sexual misconduct in the workplace.

As if adjusting to college life and the news that her secret crush, Reid (guest star Justin Baldoni), is gay weren't enough to handle, Amy learns that Ephram is going to be a regular fixture in her life now that he's moved in with Bright and Reid. Meanwhile, Andy, Nina and Jake attempt to move on with life after Nina decides which man she loves---which is Jake. Bright and Ephram take Hannah to a college party.

Andy gets involved in a case dealing with 17-year old Ethan Harcourt who is on anti-depressants since his older brother's car accident and death, but now wants to be intimate with his current girlfriend. Although, the anti-depressants he is taking is causing erectile dysfunction for him and tries to coerce Andy in letting him have Viagra. Ethan wants to keep all of this a secret from his girlfriend and family who don't know about his situation.

Andy wavers that he's too young but Ethan doesn't listen and purchases medication online that inevitably ends him up in the hospital after

A very-much-in-love Ephram discovers that he has unwittingly become a "girlfriend" to Amy, but the friendship takes a turn for something more when a moment of intimacy leads to them waking up together the next morning. Meanwhile, Nina grows suspicious of Jake's recent strange behavior, which is further amplified when his brother, Brian (guest star Tom Parker), shows up unexpectedly. Delia takes up with the popular girls in school, which worries Andy. Also, Bright tries to rectify Hannah's low self-esteem issues. Lastly, Rose drops some startling news on Harold, which could drastically change their lives.

Just out of the hospital and wanting to start his life over, Reid asks Amy out on a date. Amy talks a very reluctant Hannah into a double date with Amy's friend Nick, leaving Bright to deal with his pain and jealousy. Delia panics when her Bat Mitzvah falls on the same day as the birthday party of the most popular girl at school. Nina tries to deal with her confusing emotions over Andy and realizes she will have to make a decision when Jake asks her to move to Los Angeles with him. Harold points out to Rose that they were so caught up in the adoption procedure they've been taking each other for granted.

While packing up her house and preparing to leave Everwood with Jake, Nina tells Hannah that she knows Andy bought an engagement ring for her. Hannah convinces Nina to sneak into the house while the Browns are out to get a look at the ring. Later, Jake finds out about the ring and confronts Andy once again about his feelings for Nina. At Delia’s Bat Mitzvah, Amy watches Ephram with his new girlfriend Stephanie, and realizes her feelings for Ephram are still strong. When one of Harold’s patients leaves her baby on the Abbott’s doorstep, Harold wrestles with the right course of action while Rose immediately becomes attached to the little girl.

After their house has been sold, Nina and Sam temporarily move in with the Browns. Wanting to take care of an unresolved issue in his life before he can propose to Nina, Andy takes a mysterious trip. Bright learns that Hannah has received a scholarship to Notre Dame and is devastated at the thought that she may accept it. Edna upsets Harold and Rose when she reveals her plans to leave Everwood. Delia is thrilled with Andy’s belated Bat Mitzvah gift.