- Bright's realization of how bad off Colin is after he awakens from his coma
"I don't like it any more than you do, but he's not the guy we grew up with. If he was, I wouldn't still miss him."
- The montage of Colin's preparation for his final surgery is sad enough, but add this song playing over the scenes, and, well...
- Even worse, Colin outright makes Andy promise to let him die if something goes wrong during the surgery or he comes out of it wrong. Whether this makes the season 2 premiere more or less heartbreaking is up to the viewer.
- The season 2 premiere, which brutally yanks the rug when halfway through it's revealed that Colin didn't survive the surgery that closed season 1.
- Reid attempting suicide in season 4.
- The death of Irv Harper in season 4, Edna's refusal to deal with her grief and ultimately breaking down in tears when she's alone after his funeral.
- The season 3 finale, Ephram opening a graduation gift his mother bought for him years ago, a copy of Oh, The Places You'll Go with a letter to him written on the back of the insert page.
- Rose's cancer ordeal. Amy cries on Hannah's shoulder when she tells her about it, and Bright tears up very easily over it. Harold is beside himself with grief, thinking Rose's backaches weren't anything to worry about, and ends up praying for God to "fix this" in the bathroom during Rose's surgery.
- Andy verging on a Heroic B.S.O.D. after Harold gives him a major "The Reason You Suck" Speech in the season 3 finale, realizing his reasons for moving to Everwood have all been for naught and that with Ephram gone and Delia growing up he doesn't feel needed anymore. Turns into a Heartwarming Moment when Harold, feeling guilty for taking his stress out on Andy with the aforementioned speech, throws a We Love You Dr. Brown party with pretty much every one of Andy's past patients in attendance.