The 5 Most Annoying Things Derek Ever Did (& 5 Sweetest)

McDreamy was the center of attention for a long time on Grey’s Anatomy, but not everything he did was so dreamy.

The hit medical drama Grey’s Anatomy just kicked off its record seventeenth season with a two-hour season premiere. The series revolved around the trials and tribulations of its central protagonist, the brilliant surgeon Meredith Grey.

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Yet, there was a time when Meredith’s lover, fianceé, and eventual husband Derek Shepherd caused the fans to swoon left, right and center. However, while McDreamy had some incredibly sweet moments, he also did things that weren’t dreamy at all and were in fact, particularly annoying.

10 Annoying: Forgot to Tell Meredith He Was Married


Derek was married to a successful, gorgeous obstetrician Addison Montgomery Shepherd when he started going out with Meredith. Yet, he forgot to mention this crucial detail before both he and Meredith were head over heels in love with each other.

Of course, his relationship with Addison was strained at the time but that did not absolve him from becoming the age-old cliché of the lover who forgot to mention he was married.

9 Sweetest: Encouraged Bailey

Derek was surprisingly sweet and motivating to Miranda Bailey who was chief resident at the time.

He was there for her when she ran low in confidence or doubted herself as a surgeon. She was also one of the few people with whom he shared details about his own past, such as when he was overweight or played the saxophone in the school band. The connection between them was unlikely and sweet.

8 Annoying: Told On Richard

Derek Shepherd and Richard Webber

One rather annoying thing Derek did was to tell on Richard to manipulate the board into making him the Chief of Surgery instead.

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True, Richard was falling off the wagon and had started drinking again, so he was probably not best suited for his position as Chief of such a major hospital. But the way Derek used that against him seemed petty and underhand.

7 Sweetest: The Post-it Wedding

‘MerDer’ was forever making Meredith Grey and Drek Shepherd one of the most gorgeous, romantic, and beloved couples on popular television.

One of the sweetest moments the two shared was when the two whipped up a post-it to jot down their marriage vows. Fans will remember the moment when instead of having a traditional church wedding, Derek got married to Meredith in a post-it wedding. The vows were framed and the post-it is even today shown hanging on the wall at the Shepherds’ house. Although the two did have a legal marriage, later on, it was the unpretentious little understanding between the two that fans remember as their wedding.

6 Annoying: Was Toxic To Amelia

There were times when McDreamy became less dreamy and spouted toxins, jolting him and his fans back to reality.

For instance, his behavior with his little sister Amelia was particularly annoying. He claimed that he had looked after her from a young age and had taken responsibility for her, but when it came to being the patient, understanding older brother, Derek failed miserably. He was surprisingly egotistic and never gave Amelia the credit she deserved as a brilliant surgeon herself.

5 Sweetest: Connected Instantly With Zola

Derek with Baby Zola Grey's

Derek’s connection with little Zola was one of the high points of the at times conflicted character. He first came across Zola as a patient–the latter had a condition called spina bifida– when Alex Karev brought over a group of young African children as part of his project.

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Derek absolutely adored her and felt an instant connection with the little one. He knew at once that he wanted to adopt her and give her a home. The scenes with Derek holding little Zola, both lighting up in sheer happiness, were heartwarming indeed.

4 Annoying: Went Back On His Word

Ellen Pompeo and Patrick Dempsey

Just as he could be a jerk to his sister, Derek could also be an annoying chauvinist when it came to Meredith. Derek had promised Meredith that he would take over looking after the kids, taking a step back from his very prolific career so that Meredith could concentrate on hers instead.

This was decent of him no doubt, but then shortly after he had made that promise, he involved himself in a project with Callie Torres, the Head of Orthopedic Surgery, and got more and more embroiled in work as he was asked by the President to head a project on brain mapping. To take on such responsibilities after he had expressly told Meredith that he would take a break was neither cool nor fair.

3 Sweetest: Stayed By Mark’s Side

Patrick Dempsey with Eric Dane Grey's

Derek was shown harboring conflicting feelings towards his best friend Mark Sloan in the early seasons, as Mark was the one that his ex-wife Addison had cheated on him with.

Yet, once Addison was out of the picture, Derek warmed up to him again. When the little group of doctors from Seattle Grace-Mercy West was in that horrifying plane crash in the middle of nowhere in the season 8 finale, Mark was one of the major victims, alongside Lexie who had died on the spot. Mark managed to survive for about two months after which he was pulled off life support, respecting his own wishes. All past differences were forgotten and Derek stayed with his friend until the last moment.

2 Annoying: Put Meredith In The Spot

Not only did Derek go back on his word to Meredith and get involved with serious, time-consuming projects, he also put pressure on Meredith to give up her friends, and career in Seattle and move to DC.

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In fact, he felt entitled enough to take care of Meredith’s career without even asking her, using his influence to get her a position as a general surgeon at a DC hospital. Putting Meredith in the spot and expecting her to give up her life at a moment’s notice wasn’t something one expected from McDreamy and was frustrating, to say the least.

1 Sweetest: Alex & Izzie’s Wedding Was His Idea

Contrary to his less proud moments, some of the gestures Derek made were exceptional. For instance, fans might remember that it was his brainwave to get Alex and Izzie married in a sudden, unplanned white wedding in season 5.

Izzie had just been diagnosed with cancer at the time and was preparing for a major, potentially life-threatening surgery. She casually told Derek as part of an ordinary conversation that she saw Alex in her future. And this gave Derek the idea that Izzie and Alex could get married that very day in the same church that had been booked for his own wedding with Meredith. It was an uncommonly sweet gesture on his part, and everyone played along.

NEXT: Grey’s Anatomy Derek Shepherd’s Transformation Over The Years (In Pictures)

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Updated: November 18, 2020 — 1:00 am

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