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Derek recovers well and Callie clears him to return to work, but it is still weeks later that he feels ready to operate.Derek, Callie and fellow resident Jackson Avery decide to do nerve transplant for his hand.
Since their divorce they have remained on amicable terms, with Addison even admonishing Meredith for breaking up with Derek in season three.As Meredith nears the end of her fifth year of residency, she and Derek are torn between staying at Seattle Grace Mercy West or leaving for Boston where Derek would work at Harvard while Meredith would be at the Brigham and Women's Hospital.Following his rescue from the plane crash that killed Mark and Lexie, Derek learns that he may only regain 80 percent of his hand's function.Shepherd was formerly the Chief of Surgery at Seattle Grace Mercy West Hospital, but abruptly resigned as chief in season 7 following the shooting.For his portrayal of Shepherd, Dempsey was nominated in 20 Golden Globe for the Best Performance by an Actor in a Television Series Drama for the role, and the 2006 SAG Award for the Outstanding Performance by an Actor in a Drama Series award.Derek's plans to propose were ruined by a series of unfortunate events in season five.
In the season finale, they decide to give their planned wedding to Alex and Izzie.
In the Private Practice episode "Ex-Life" Derek finally tells Addison that his mother never liked her in the first place.
He admits to Meredith that Addison cheating on him with Mark was partly his fault as an absentee husband.
With mixed feelings, Derek offers him an ultimatum: go into rehab and possibly pick up where he left off after, or quit completely.
In seasons three and four, Meredith and Derek's relationship becomes rocky and they each take time to date other people.
Before his death in 2015, Derek was happily married to his longtime girlfriend Meredith Grey (Ellen Pompeo).