Derek Shepherd was a beloved character on Grey's Anatomy, and fans were left heartbroken after his untimely death. Throughout his time on the show, he proved to be a brilliant surgeon, a loving husband to Meredith, and a great father to his children.
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Yet, with all the good aspects of Derek's personality, there are many things he did that are questionable when looked at in retrospect, especially when it came to his relationship with Meredith. Derek often acted selfishly and could be quite conceited at times, leading to many instances that wouldn't hold up today.
After the iconic return of Addison at the end of season 1, Derek's relationship with Meredith became fractured as Derek had to choose between the two women. Ultimately, Derek chose to try and save his marriage, leaving Meredith heartbroken. However, Derek became jealous of Meredith's love life and began to resent her, especially in the workplace.
This resulted in him treating her harshly, singling her out, and ridiculing her for mistakes in front of the other interns. One of the main instances of this came in the episode "Much Too Much," when someone that Meredith had slept with turned up at the hospital and required medical help from none other than Derek himself. Derek, clearly jealous, made inappropriate jokes at Meredith's expense that wouldn't fly today.
The plane crash at the end of season 8 was one of the saddest episodes in Grey's Anatomy history, and the aftermath was just as heartbreaking. Season 9 was a dark time for the doctors at Grey Sloan, and Derek had a particularly hard time dealing with grief and the injury to his hand he sustained in the accident.
However, whilst the other doctors wanted to move on from the crash, Derek was insistent in finding the person to blame for the ordeal, which ended up being Owen. Owen changed the plane companies due to budget cuts in the hospital's finances, and Derek held a lot of resentment towards him. "The End Is The Beginning Is The End," showcased Derek's hostile treatment of Owen, and whilst some of it may have been justified, in retrospect it was mostly just unfair.
Meredith and Derek were the 'it' couple of season 1, and it seemed like nothing could interfere with their budding romance. And then, Addison Montgomery showed up in "Who's Zoomin' Who?" promptly ending Meredith and Derek's relationship when she divulged the fact that she was his wife.
Whilst Derek's escape to Seattle to get away from Addison after she cheated on him made sense, keeping Meredith in the dark the whole time they were together did not. In hindsight, it would have just been easier for Derek to be honest with Meredith from the beginning - even if he was hurting from the betrayal, he shouldn't have started a relationship with Meredith without telling her the whole truth as he knew it would eventually come out anyway.
Derek was understandably broken-hearted after learning about Addison's affair with Mark but eventually decided to give his marriage another shot. However, when they got back together in season 2, he did everything in his power to remind her of her betrayal.
Yet, in season 1 he had begun a relationship with Meredith and still harbored feelings for her throughout season 2, even sleeping with her in "Losing My Religion." Derek constantly begrudged Addison and insulted her because of her actions, yet committed similar sins. On reflection, perhaps Addison wasn't the villain she was made out to be upon her introduction, as she and Derek were ultimately just as bad as each other.
After a surgery went wrong and a woman died at his hands, Derek elected to quit his job and hide away in his trailer in the woods. This resulted in Derek spiraling into a depression, and pushing everyone away, including Meredith. The episode "I Will Follow You Into The Dark," detailed this, and showed Webber attempt to break through to Derek by telling Meredith that he was planning to propose to her.
However, the well-meant plan went awry when Meredith confronted Derek, only for Derek to unceremoniously bat the engagement ring into the woods. Considering all that Meredith and Derek had gone through, it seemed wrong for him to push her away when she was the closest person to him. Whilst it was true that he was hurting, looking back his actions were hurtful to Meredith and completely unnecessary.
Amelia and Derek's relationship was notoriously up and down, as Derek often switched from supporting his sister's endeavors to undermining her completely. Upon Amelia's introduction to Grey's Anatomy, Derek constantly put her down and chose to focus on her actions from the past, rather than the person she had grown to be.
One of the main examples of this occurred in the episode "Could We Start Again, Please?" when Amelia's history as a drug addict was exposed to the hospital, and Derek failed to stand up for his sister. Instead, he went behind her back to talk to Owen about the situation, nearly getting Amelia fired in the process. Derek always insisted that he was a family man, and therefore should have respected and cared for his sister more.
Derek certainly transformed over the years, but by season 11, it seemed he hadn't lost his egotistical and selfish streak. Meredith and Derek's relationship was in a fractured state throughout this season after Derek begrudgingly gave up moving to DC to fulfill the promise he made to Meredith of prioritizing her work.
In the episode "Only Mama Knows," Derek cruelly tells Meredith: "You sound just like your mother." Considering Meredith's relationship with her Mom was never great due to how Ellis neglected her in favor of work, Derek's words were a cheap ploy to guilt Meredith for putting herself first. These days, it is not unfathomable for someone to have a promising career and be a good parent, and Derek's reference to Ellis's cold ways was an unfair, and frankly outdated, insult.
Whilst Derek was widely considered to be one of the best surgeons at Grey Sloan, there were times that he acted unprofessionally. One of the most notable examples was Derek's penchant for dating his colleagues - not only did he have a relationship with an intern (Meredith), he also dated Rose, one of his scrub nurses.
When his and Rose's relationship ended, he made her feel uncomfortable in the workplace, going as far as to shout at her when she accidentally cut him with a scalpel. Derek should have been more professional in his job, especially considering the high-stakes nature of the work. And, when having romantic relationships with his colleagues, he should have been able to draw the line between his work and his love life.
Derek and Meredith's relationship was in a critical state after Derek left for DC, and the cracks really began to show in "With Or Without You." The episode included flashbacks to Derek's time in DC, where he gradually got closer and closer to one of his research fellows, eventually kissing her.
Whilst Derek expressed his guilt for cheating on Meredith, there was no real fallout from it, and with the added benefit of hindsight, he was let off the hook quite easily. It's easily one of the worst things Derek did, and yet it was written off as just a small mistake that was quickly forgiven.
One of the biggest things Derek did that doesn't hold up today was when he promised Meredith he would step back from his work so she could focus more, and then promptly went back on his word. "Fear (Of The Unknown)," saw the couple reach breaking point, as Meredith realized that if she were to move to DC with Derek, she would also be in the shadow of his career. Derek decided to stay and live up to his promise, only to leave a few episodes later.
His ego was one of the things that made Derek an overrated character, and this instance proved it. He tried to pressure Meredith to do something 'worthy' to make him staying in Seattle justified, and eventually decided to go to DC to pursue his career anyway. It was a selfish move, and it never made sense for Derek to expect Meredith to leave her home to follow him, or to leave Meredith and their children, even if it was a job for the President.
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