Grey's Anatomy: 5 Worst Things Derek Has Ever Done (& 5 That Deservedly Made Him McDreamy)

Although he may have been given the nickname McDreamy, Grey's Anatomy's Derek Shepherd did not always earn it.

Sixteen seasons in and Grey's Anatomy is still running strong. Over the years characters have come and gone. Derek Shepherd, also known as "McDreamy," was the Head of Neurosurgery at Grey Sloan Memorial Hospital. After eleven seasons, Derek's time on the show came to an end and his character passed away, leaving behind his wife Meredith Grey and their children.

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Derek was considered one of the best surgeons. Given his track record of lives saved and his way of smooth-talking and charming other people, he was considered to be a relatively decent guy. Unfortunately, not everything he did on the show was good.


"How To Save A Life" documents the last day of Derek Shepherd's life. His job in D.C. has caused nothing but issues between him and Meredith; however, before he died, Derek had planned on quitting his job to be around his family more.

Fate had other plans and Derek never got the chance. On his way back to work, a car parked on the side of the road got his attention. Derek quickly pulled over to help the people in need, determined to save their lives with the small number of supplies he had. In the end, he manages to succeed, keeping everyone alive until the ambulance arrives. Quickly afterward, Derek is hit by a semi-truck, causing the accident that ends his life.


After sleeping together the night before, neither Meredith or Derek expect to see the other at Seattle Grace Memorial Hospital. While Meredith is starting her internship, Derek is starting as the Head of Neurosurgery. While Meredith insists the two keep their relationship professional, Derek continuously pesters her about moving forward in a romantic relationship.

Meredith repeatedly disagrees but he is relentless. Eventually, Meredith agrees, having their mutual attraction outway the risks of the others finding out. However, Derek left out one very important detail to Meredith, he was still legally married.


In the aftermath of a shooting at the hospital, Cristina is traumatized after staring down the gunman in the operating room. After avoiding surgery for a while, those close to her are worried as it goes against her determined nature. While it was not Derek's idea, he does show up to be there for Cristina when Owen asks him to take her out fishing.

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Cristina is fidgety and uninterested in sitting still and Derek gets agitated by her constant movement. It is not an easy time at first, with both relatively uncomfortable. By the end of their time on the water, they have caught a fish and go to take pictures. About to take the photo, Cristina stands in front of the camera and unexpectedly begins crying. Derek tells the photographer to take the picture, saying that Cristina would want to remember this moment, as it is the beginning of her moving forward.


When his wife shows up at the hospital, Derek needs to choose between pursuing a relationship with Meredith and fixing his marriage with Addison Montgomery. After Meredith tells Derek he should pick her, he decides to choose Addison.

However, not only does Derek not bother to try to work anything out with Addison, he insults Meredith's life choices when she tries to move on. While Derek and Addison had agreed to try, Derek can not look past what he deems to be her issues and makes it difficult for Meredith to focus on her future.


Not everyone needs a big or flashy wedding to lead them into a marriage. Derek and Meredith needed nothing more than a post-it note. After planning a large wedding, they decide to give it to good friends Alex Karev and Izzie Stevens.

While Izzie wanted the large wedding, neither Derek or Meredith cared for all the extras, and instead had a sweet moment between the two of them, saying their vows aloud while writing it down on a post-it note. Although they make their marriage legally official later, the post-it note is considered to be their main marriage certificate.


Derek was justifiably angry to know that Addison and his best friend Mark Sloan had an affair. However, Derek's anger ends up going overboard, as he blames them both entirely for the failed marriage.

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While Mark and Addison had both agreed that they were in the wrong to have an affair, they also say they knew that Derek was not treating Addison right during their marriage. The problems in Derek and Addison's marriage were not just one person's fault, but it took Derek too long to understand his faults.


A boat disaster in Season 3 leads Meredith Grey, Derek Shepherd, and other doctors to the scene. Meredith attempts to help a young girl who pushes her into the water. She shuts down, not actively fighting for her own life.

Derek jumps into the water, pulling her out. He carries her out of the water and Meredith is saved by fellow doctors. Derek is frantic while Meredith is in the operating room, hoping that she will come out of this alive. It is a truly vulnerable moment for him and after the emotional confusion that was faced in the previous season, was the evidence that showed how important she was to him.


Amelia Shepherd did not have an easy go of it. Addicted to drugs and alcohol, it took her longer than Derek to get to a place where she felt confident and in control. As she spends more time around, it is shown that she is a competent surgeon.

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Derek's ego prevents him from not only admitting she is good but being comfortable with Amelia receiving the Head of Neuro job while he still works at the hospital. Amelia had enough insecurity already, something that she fought to be confident in herself as a surgeon and a person. The last thing she needed was to feel like she was not good enough by her older brother.


Derek and Meredith's relationship had many ups and downs before they were able to find themselves in a happy place, and even then trouble still found a way of following them. Amid the drama that surrounded the hospital and their personal lives, Derek found the time to build the dream house for himself and Meredith.

As they grew their family, their first two children would live in the house as well. It took time but Derek, with the occasional help of some friends, managed to complete the home he and Meredith wanted for themselves.


After arguing with Meredith over taking a job in Washington D.C., Derek decides to take the position regardless of what his wife wants. His determination and ambition to be the best were the deciding factors, rather than Meredith not wanting to move since everyone she loved was in Seattle.

At the new job, Derek had a research assistant he got a little too close to. Shortly before his death, Derek and his research assistant shared a kiss. The moment did not lead to anything further, however, that does not mean it never happened. Beyond that, Meredith did not know about it.

NEXT: Grey's Anatomy: 10 Things You Didn't Know About Meredith And Cristina's Friendship

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