All of Derek Shepherd’s Love Interests in Grey’s Anatomy, Ranked

Fans had no idea about the impact the terminology "McDreamy" had on television viewers in the 2000s and the chemistry was off the charts when Meredith Grey and Derek Shepherd first made contact. Despite having a turbulent relationship, "MerDer," as the fandom likes to call it, went down in Grey's Anatomy's history as the most iconic couple of all time. Looking at the two, it's almost impossible to imagine that both Meredith and Derek would have been with other people, but what's a Grey's Anatomy romance without a juicy drama?

Although their love story suffered an unfathomable tragedy, Derek and Meredith's relationship is considered a hallmark of romance. However, when it comes to relationships, Meredith's list may be longer than Derek's, but the hot neurosurgeon also had his fair share of flings while navigating his relationship with the beautiful intern.

4 Derek's Fling With Sydney Heron Was Short-Lived

It Was an Awkard Encounter

derek takes sydney heron on a date after breaking up with meredith

Derek Shepherd was the guy of many women's dreams in Grey's Anatomy. Although his eyes were always set on Meredith after their one-night stand, there were times when he was forced to explore other options. Derek and Meredith's relationship wasn't exactly easy, especially with the difference between their career trajectories. So, during their on-again-off-again period, the two expanded their horizons and decided to give dating other people a chance. However, in Derek's case, he ended up going on a pity date with the zealous Sydney Heron. Fans may very well remember Miss Sydney because of her contagiously positive attitude that rubbed many doctors and interns the wrong way.

Although it's astounding for fans to imagine even a single scenario where Derek would go out with someone like Sydney, it did happen. Derek was still hung up on Meredith when he went out with Sydney, and while it wasn't his brightest moment, it was sweet. The show might have thrown in this little interaction as a way to make Meredith jealous, but surprisingly, Sydney would have been all in if this had been what Derek was looking for. Before he could gently break it off with her, Sydney put a stop to the whole thing, implying that Derek wasn't ready for the kind of relationship she wanted, and that was that.

3 Dating Rose Did Not End Up Well For McDreamy

She Did Not Take the Breakup Well

derek and rose feel awkward as mark and addison make fun of him

It's surprising that someone as smart as Derek would think that dating a nurse would be far better than having a relationship with a surgical intern. Yes, there also came a time when McDreamy had an intense fling with a scrub nurse. It all started when Derek grew frustrated with Meredith's inability for intimacy and serious emotional attachment. Her dysfunctionality with relationships stemmed from the trauma caused by her father, mother and Richard Webber's complicated dynamics. After trying to make it work out, the two eventually had one out of their many breakups, and Derek just decided to move on.

When Rose and Derek had an intense moment during a navigational system failure in one of his surgeries, the two couldn't defy the chemistry between them. After the surgery, she and Derek made out in the scrub room and soon after, started dating. It's understandable why Derek would opt for someone like Rose because, at that time, she seemed a less tumultuous option than Meredith, who was in therapy during their relationship. Despite going on a couple of dates and even sleeping together, Derek later confesses to Mark that he couldn't stop thinking about Meredith even when he was with Rose.

Played By

Lauren Stamile

First Appearance

Season 4, Episode 8, "Forever Young"

Last Appearance

Season 5, Episode 2, "Dream a Little Dream of Me, Part 2"

Fortunately, both Derek and Meredith came to their senses as the success of their clinical trial pushed their repressed emotions to the front, and they reconciled. Meredith made a grand gesture by decorating Derek's land with candles in the shape of the house she wanted to have with him. Accepting that Meredith is finally finding it in herself to commit to him, they kiss, and Derek later breaks up with Rose. The scrub nurse doesn't take it well and impulsively stabs Derek's hand during surgery in anger. Ashamed of what she did, Rose later transferred departments, and that was the end of her and Derek's brief love story.

2 Addison Was Derek's Only Long-Term Relationship Before Meredith

Their Marriage Was Already In a Bad Place When Addison Cheated

Addison Montgomery smiles and shakes Meredith's hand as they meet in Grey's Anatomy.

Addison Montgomery's entrance in Grey's Anatomy is the show's most memorable moment. On top of that, the revelation of her being Derek's wife was hands down epic. It's safe to say that in the medical drama's golden years, Derek and Addison's marriage was the biggest reveal of all, of course, next to the cause that broke their marriage in the first place. Before they tied the knot, Addison and Derek were close friends, having gone through medical school together and enjoying a similar way of life. Before Meredith, Derek's only meaningful relationship in the romance department was with Addison, who was his wife for over a decade.

Ironically, their soaring careers became the reason for their crumbling marriage. Both doctors were exceptional in their fields and ran private practices. They eventually grew apart because of their busy lives and putting effort into their marriage, especially Derek. Unfortunately, the loneliness got the better of Addison before Derek, and in a moment of weakness, she cheated on him by sleeping with his best friend, Mark. Derek broke things off, sold his private practice and moved to Seattle, where he had a one-night stand with Meredith, and their story began. After a while, Addison came to Seattle Grace Hospital to reconcile with Derek, and she almost broke Meredith and Derek apart in the process.

She later realized that she was doing more damage than good because even she wasn't in love with Derek anymore, and her attempts were coming from a place of guilt. They eventually got a divorce, and Derek confessed that it wasn't all Addison's fault and that he was the one who stopped existing in their marriage first by being absent all the time. Fortunately, Addison remained a healthy part of both Derek and Meredith's life as a confidant and a family member of sorts.

1 Meredith and Derek's Love Story Is One Of the Most Popular In Television History

Their History Is Long and Rich

Meredith and Derek smile at each other during their first meeting at Joe's bar in Grey's Anatomy.

Meredith stands behind Derek and an irritated Addison in the elevator in Grey's Anatomy.

Meredith and Derek write their wedding vows on a blue Post-it note in Grey's Anatomy

meredith and derek proposal

Meredith and Derek's relationship was like a whirlwind, keeping fans on their toes about whether they'd end up together. The two doctors had their fair share of ups and downs, which only cemented the fact that their relationship was based more on practicality than fantasy. After overcoming great odds, such as Derek being married, Meredith ruining his trial, and the two growing apart when Derek decided to go to D.C., "MerDer" got through, at least romantically. Although McDreamy's death would forever hauntGrey's Anatomy fans, it in no way left their love story incomplete. Derek's death was a turning point in Meredith's life, proving how deep their love was.

Their story may have started out as a fairytale, but their journey wasn't easy. Meredith and Derek's love and marriage not only survived extraordinary circumstances but also each other. When Derek hit a new low after getting shot, it took him a while to get back on his feet. Instead of leaving him out to dry, Meredith supported him and waited for him to heal just like he had. After a while, their relationship hit rock bottom when Meredith sabotaged Derek's trial, and he couldn't find himself even looking at her. It completely broke them until they got Zola into their lives, and the two found common ground to move on. When their family started to grow, Meredith and Derek found themselves at odds with deciding whose career mattered the most.

As a woman and a mother, Meredith's career naturally took a hit while Derek thrived, and he eventually chose his ambition over her. However, the biggest obstacle in their marriage came in the shape of Derek's move to D.C. when he took up the President's offer to lead the Brain Mapping Initiative. During his time in D.C., Derek eventually got close to a fellow researcher, who developed romantic feelings for him. Right after the woman tries to kiss him, Derek realizes that he has taken Meredith and his marriage for granted. He flies out, and after much effort, the two make up. This was the last time fans saw the iconic couple in their tender moments because what came next almost broke the fandom. Derek Shepherd tragically lost his life after negligence on a hospital's part that was unprepared to tackle a trauma of that caliber.

Ultimately, Meredith Grey became the last woman Derek Shepherd had been with and was the center of his universe. After going through countless life-threatening situations, from being shot by a lunatic to surviving a plane crash, Meredith and Derek reflected on different aspects of how a relationship is built to last despite what fate has in store. Although Meredith moved on with her life, she never forgot Derek, and he was the partner she remembered when she was at death's door. Their love was imperfect but more lasting and inspirational than any fairytale.

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