Grey’s Anatomy – 14 Worst Times A Character Cheated, Ranked

 The ABC interpersonal drama Grey’s Anatomy has been on for years and years, and it is built largely on the myriad convoluted romantic entanglements, ripe with drama and angst. Some relationships, such as Jackson’s with April, with whom he is currently committed, are based (in part) on the ability to be faithful, even in the fascination of possible attachments, ie, to exes. The ongoing infidelity motif – incarnated, for example, in Alex, Derek and Owen – including frustration and anguish over these characters being with other women, is in itself a tangle of sex that creates the drama and, for many fans, works as a sustaining draw to its faithful viewers.

Relationship drama has long been a staple on the ABC medical drama Grey’s Anatomy, a show populated by a cast of wonderfully messy characters whose romantic entanglements and extramarital affairs – even the beautiful and beloved Meredith and Derek cheat! – reflect many of the ways that human beings’ lives are complicated in any given day. Whether it’s falling in and out of love, being in love with someone who is romantically unavailable or intruding on the dark and gritty side of relationships, Grey’s Anatomy has gone there.

Although Grey’s Anatomy began centred on Meredith Grey (Ellen Pompeo) and a class of residents, it came to revolve around multiple generations of doctors and medical students, all related in some way to each other, and all of whom have at some point their own storylines. The series is as much about sex and relationships as it is about medicine. The characters have been in love and suffered lovesickness, yes, but they’ve also cheated on their partners and been unfaithful in general – some to an absurd degree. Some of these creative choices flat-out derailed the arc, while a few made sense in the larger scheme of things.

Grey's Anatomy Feature Image

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14 Jackson Avery On Maggie Pierce

Jackson Never Emotionally Let Go Of April

Jackson and Maggie talking while upset in Grey's Anatomy

Jackson didn’t sleep with anyone else. That’s the key difference between Jackson and alls Anatomy characters who cheated on their partners. Jackson is extremely loyal. He even drops along about how he has a hard time doing even artistic works with subjects who weren’t his wives.

When he’s not spending time in a monastery in Seattle, Jackson secretly meets up with another woman (and). This happens while he’s still with Maggie. ‘I didn’t cheat on you!’ he yells at one point, and the relationship does indeed recover from this grievance. However, it never wholly recovers, probably because Jackson is still in regular contact with April, his ex-wife with whom he had a nasty breakup in season 16 between the two of them admitting they never really liked each other as much as they should have.

Maggie fears the emotional hold that these other women have on him, and she’s actually got it right about Jackson. He won’t cheat on her with sex, but he always loves April, and eventually he returns to his ex-wife a decade after their divorce.

13 Owen Hunt On Emma Marling

Owen Had A One-Night Stand With Cristina

Owen and Emma looking serious attending a wedding in Grey's Anatomy

Although fans might not want their favourite characters to be unhappy, this does not mean that they are okay with their actions. Not everybody agreed with the way that Owen and Emma’s relationship ended. Owen had a one-night stand with Cristina, and then cheated on her by breaking up with her. This was bad since Emma agreed to stay-at-home and they moved in together. Owen slept with Cristina, and then broke up with Emma. This was very sad.

A lot of fans didn’t see it, though: Cristina and Owen had already decided, on the assumption that they both wanted to stay in the same place, that they wouldn’t work anymore because they didn’t want to be with the same person forever; so why were the writers bothering to mine this storyline again? It was even worse that Owen and Emma appeared so happy. Why make it so obvious that you were scrapping Emma so quickly? ‘It just looks really bad when you do it to Owen.

12 Alex Karev On Izzie Stevens

Izzie Catches Alex Sleeping With Olivia

Alex and Izzie fighting in Grey's Anatomy

At the start of the show Grey’s Anatomy, you see a self-centred and ethically lacking Alex Karev, who is crude and rude to fellow guests and servers alike. Later, when Karev finally settles with the lovely Izzie Stevens, he cheats with the nurse Olivia, succumbing to the pressure of the blossoming romance. Karev is unable to commit and share intimacies with Izzie, so he hooks up with Olivia. Worse still, Izzie catches the two in the act, and promptly cuts the relationship short.

Alex and Izzie weren’t actually together, to be fair – they were just working up to something nice. They might have ended up together eventually. And Izzie was the one who basically talked everyone into giving Alex another chance, after she saw that “soft side” and all. You would have thought that the guy who was having one-night stands while giving Izzie false hope – that’s not the direction you want your character to go. At the very end, Alex came back to Izzie, because he found out that she had his kid, but that’s not really his moment.

11 Nathan Riggs On Megan Hunt

Nathan Cheated On Megan Years In The Past

Nathan proposes to Megan on Greys Anatomy

Grey Sloan Memorial hospital didn’t have Nathan Riggs for long; he was Owen Hunt’s former military colleague and the fiancé of Owen’s sister, the plastic surgeon Megan. When Meredith Grey’s cat caught Nathan Riggs’ gaze, the fellow got on board Grey’s Anatomy. When he and Meredith began an affair, Nathan wanted to keep it secret, insofar as his long-ago adultery with a flight attendant was no one’s business anyway. When Megan, who’d been missing overseas, finally showed up and was put in a coma in Seattle, Nathan wanted to reunite with her – but that, like Riggs, wouldn’t last for long.

Megan also cheated on Nathan, though the full details of her side struggle to be revealed, while we’re repeatedly shown Owen haranguing Nathan for cheating on his sister – fact confirmed when he’s shown to have given Megan the necklace of the other woman he cheated with. OK, so after surviving the plane crash, Owen had gone to great extremes to find Megan – and had moved heaven and earth once she was found alive. Yet there was still no getting past his history of cheating.

10 Addison Montgomery On Derek Shepherd

Addison Created On Derek With His Best Friend, Mark Sloan

Addison and Derek looking at each other on Grey's Anatomy


The medical drama’s erstwhile second fiddle, Kate Walsh signed on to play Derek’s wife, and a third spike to a Meredith-Derek love triangle soon sprouted that didn’t detract from theirs, but demanded plenty of attention. Meredith left Derek because what she went through stemmed from Addison’s cheating on Derek in seasons before the beginning of Grey’s Anatomy proper – on his best friend, yet. The two saw each other when Derek was dating Meredith Grey, and Meredith was left for her.

But then she cheated on him with Meredith, and they ultimately got divorced. Of course, had Addison not cheated in the first place, Meredith-Derek would not have happened in the first place, but – ignoring that – she was really a loser for sleeping with her husband’s best friend. Neither was a saint of fidelity, and neither was happy until they broke up for good and moved on with their lives. Addison shouldn’t have cheated. But it wasn’t to be.

Grey's Anatomy Derek Meredith Couple Featured Image

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9 Derek Shepherd On Addison Montgomery

Derek Cheated With Meredith Grey

Addison dancing with Derek in Grey's Anatomy

Any fans who had thought that Addison and Derek would actually stay together after their first marriage saved, and who hadn’t given up all hope for season two were thoroughly disabused of their delusions that the two would make their marriage work when Derek cheated on Addison… again. The two had started the series on a rocky road, having separated because Addison cheated on Derek with Meredith. They worked their way back to each other, but he cheated on Addison with Meredith. Again. It shouldn’t have come as a shock to anyone since, by then, Meredith was manifestly the woman that he loved.

But, rather than telling Addison the relationship wasn’t working for him anymore, he slept with Meredith in the on-call room. Although many Meredith and Derek fans were happy that their favourite couple was getting back together, they didn’t want Addison to get hurt. It is worth noting that Derek was familiar with the pain of being cheated on, as Christina had previously cheated on him with Burke. Therefore, viewers thought it would be out of character for Derek to take this route. It was a tad hypocritical, if you ask me, after everything else that happened.

8 Owen Hunt On Cristina Yang

Owen Had A One-Night Stand With A Random Woman

Owen Hunt and Cristina Yang embrace on Grey's Anatomy.

Owen confesses his love for Cristina more than once, and he did love her – he chose her over Teddy, whom he’d had feelings for from the beginning. Of course, like several of the other romantic relationships in Grey’s Anatomy that appeared to be on the verge of success, theirs had problems lurking. When Cristina decided she wouldn’t have children and then had an abortion, the latter took revenge by sleeping with another man. Owen drank himself silly and had a one-off with a patient’s friend.

Afterward, however, to his credit, he confessed what he’d done, and they had a long, painful talk about his infidelity over wine. Owen and Cristina: the ‘will they or won’t they?’ pair for almost five years on the show. Owen’s transgression felt like a blow to the hearts of fans of the pairing. Sure, she slept with him again and forgave him, but they were ‘never going to work’, as she mentioned. And, it’s a happy ending, I guess, that they were both open with each other about their problems, which allowed them to remain close friends right up until the point where Cristina left the country for good.

7 Ellis Grey On Thatcher Grey

Ellis Had A Long Affair With Richard Webber

A side by side image features Ellis and Thatcher Grey in Grey's Anatomy

Among the biggest marital betrayals, coming before the series even began but resonating through the life of the show, was the long-drawn-out affair Meredith’s mum Ellis had with Richard Webber, even though she was married to Thatcher Grey. Ellis and Richard are soulmates; their relationship ruined Meredith’s childhood. It also ruined Meredith’s relationship with her mother (who tried to take her own life in front of her daughter).

Additionally, Maggie Pierce was revealed to be Ellis and Richard’s daughter. The secret came as a shock for everyone, except perhaps Richard, but it was welcome as Meredith could feel as if she had expanded her family after losing almost all of them. In terms of sperm donors, her dalliance also blew up her relationship with her biological father, Thatcher, who walked out on the family completely when he found out Ellis was sleeping with someone else. In Meredith’s case, this one sex partner sabotaged her relationship with her long-lost father more than anyone else involved.

6 Richard Webber On Adele

Richard Cheated With Ellis Grey

Adele looking at Richard in Grey's Anatomy

Well, if Ellis cheated on Thatcher, then Richard must have cheated on Adele, too. That wasn’t too surprising, given how happy they seemed together. But, while those two were happy together, they didn’t stay together for long – so before long we could see how bad Richard’s cheating was for Adele, since Adele wound up implicating Bailey of cheating on her husband because he’d be spending a lot of nights at the hospital. Besides, we knew how nice Adele was. The fans hated to see her suffering. But of course this was all off-screen – we didn’t see any of it until after the story began.

Fortunately, in the end, the pair patched up their relationship, but at one point some of the fans felt that Adele had been given a raw deal: Ellis and Thatcher had wrecked their marriage with infidelity, and shattered their relationship with their daughter Meredith. Richard was fortunate because he managed to save his marriage to Adele, and he managed to stop cheating, and he became a much better man in the process. But, as I outlined above, Adele never forgot it, and it illustrates how cheating often causes lifelong difficulties in marriage.

5x OverUnderrated Webber feature image

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5 Arizona Robbins On Callie Torres

Arizona Cheated With Lauren

Callie and Arizona at Izzie & Alex's wedding in Grey's Anatomy


Grey’ an American television series that was aired in 2005. Richard Webber is a splendid and old character that appeared in many seasons of Grey’s Anatomy. One of the reasons why he is an overrated character is that he is incredibly well-liked by the patients and numerous people who do not even know Charles Percy. Even though Charles Percy is a rather old character, he still gives advice to younger people. Even though he is a male, he is married to Catherine Percy from Season 10 to Season 14. Moreover, he was a beloved mayor.
By analysing Grey’s Anatomy characters, it can be seen that Grey’s Anatomy can truly be a befitting title of this series, particularly Charles Percy and his wife Catherine.

The two women seemed a beautiful couple. The fans, cheered them up throughout the series, secretly wishing them all the best as they lived a rollercoaster together, with Callie having an accident while pregnant and Arizona having her leg amputated after the devastating plane crash. However, that leg amputation seemed to destroy their relationship as Arizona felt that decision ruined her career and her life. They got over it, or so it seemed, until their eventual feud which was the backbone of the reason why they split in the first place.

What did not make sense was for Arizona to cheat on Callie with the craniofacial surgeon Lauren Boswell. Despite the fact that Arizona was definitely not okay in the aftermath of the plane crash, fans struggled with what would cause her to cheat. Lauren came in and began to immediately flirt with Arizona and, although she knew that she was Callie’s wife, it did not stop the Boswell from getting handsy. As soon as she leaned in to kiss Arizona, Callie figured out that she was being cheated on and immediately called it off. Both fans were devastated that their favourite couple had split up, and ultimately that this beautiful couple could not make it work at the end of the day.

4 Teddy Altman On Owen Hunt

Teddy Cheated With Tom Koracick

Teddy and Owen looking at each other in Grey's anatomy

Another Grey-Sloan scandal: Teddy cheated on Owen with Tom Koracick. Teddy, who is usually very controlled and logical, got Titania syndrome. Think Oberon when he fell in love with Titania, which made all sense flee his brain once, forcing them to swan around in the fairy woods high on honey for nights on end. Similar to Oberon, Teddy was with another hottie from a different troop: she was physically sleeping with Tom, whom she’d been hooking up with without falling in love before Owen proposed to her. And, worst yet, she conceived Owen’s baby when she cheated with Tom, whom she carried on regularly with, all the while secretly continuing the affair.

Teddy’s unusual response did, however, leave fans perplexed – especially since she had no plans to get back together with Tom and craved undoubtedly valid vindication by marrying Owen. Teddy might have been confused, but Grey’s fans weren’t: she was wrong to play with Tom’s feelings and give him false hope. She even actively cruel, pointing out that Tom would make a far better dad than Owen. It was a terrible situation for Owen, Tom and Teddy. Everyone in this knotty triangle deserved better.

Grey's Anatomy Parenting Decisions

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3 Alex Karev On Jo Wilson

Alex Left Jo For Izzie

Jo and Alex standing at the altar in Grey's Anatomy


Given earlier reports of Justin Chambers’s departure from Grey’s Anatomy ahead of season 16, I knew many fans were already wondering how the writers might end his storyline. Friends started emailing me their own favorite possibilities, and their own favourite fancasts for Alex’s next chapter. They anticipated that he would sell his Beverly Hills home and retreat to someplace more affordable elsewhere. They thought he might take a career detour or enroll in medical school to expand his skill set, or that he might exchange western medicine for holistic approaches.

Fans were game to consider that Alex could return to his native Switzerland, to do some bouldering. Yet I wager that very few such thinkers predicted what writers had in mind: that Alex had left Seattle to pursue a life in Kansas with Izzie and their children. The show’s writers would learn – there was widespread enthusiasm across the Alex and Izzie fandom, but no segment was more vocal than the group that felt that the end was out of character, and ‘#notfitcharacter candyassery’.

Too much of this was due, frankly, to Alex being married to Jo, and having had a future with her. Despite their bickering and disagreements, Alex and Jo never once considered ending their relationship, in part because of the support and partnership they each provided the other. Thus, having Alex so abruptly end this relationship made no sense and ultimately undermined Alex’s arc of development. It also made no sense that he would remain nearly silent after Izzie left him without a word (thinking back to how much that hurt him) and then do the very same thing to Jo

2 Derek Shepherd On Meredith Grey

Derek Cheated With Renee (With A Kiss)

Derek and Meredith exchange a post-it in Grey's Anatomy

I personally might consider one of the worst betrayals Derek’s tryst with his research fellow, Renee, in the seasons 10 and 11 of Grey’s Anatomy. After Meredith’s dream relationship with Derek suffered a collapse, when the latter moved to DC for his job. In a world of television serials with hundreds of episodes, where we began to expect the unexpected, no one expected Derek, of all characters, to cheat on his longtime queening Meredith. Meredith feared the worst, and she was almost right – Derek did kiss Renee, but we couldn’t blame him, since perhaps this kiss helped him realise the truth, and drove away any confusion he might have had.

He did return to Seattle, but for the faithful, his afternoon with the Research Fellow was galling. Yes, Derek fell for Meredith even though Addison was still alive, but we didn’t want to see him cheat on Meredith either. After all, they had been the centrepiece of the series for so long, and this was just a kiss for heaven’s sake, though close enough to scuttle the best relationship the show ever fostered. Thank goodness they made it work out for them.

1 George O’Malley On Callie Torres

George Cheated With Izzie

George and Callie wearing blue scrubs at the hospital on Grey's Anatomy

George was silly and sweet and good to the core, which made his one-night stand with Izzie and his subsequent desire to leave Callie for his sexy colleague incomprehensible. Yes, the married couple George and Callie weren’t exactly stellar0 no one would call their marriage a happy ever after0 but that wasn’t necessarily a good reason to give in to an impulse with Izzie, especially when the two characters hadn’t indicated to each other that they were attracted to one another. George and Izzie had always been friends and buddies, and not indicated anything else.

Really, isn’t the person who seemed like her perfect match back in the first season or so, George – who had a crush on Meredith instead and then went on to date Izzie – the one who lost her mind? What actually happened was less a twist than a clusterfuck: the show-runners decided to pair them up because… why not? That it happened to involve Callie – a character who’d been pretty likeable so far – made the storyline, by Shonda Rhimes’s standards, downright maddening. George cheating on Callie might have been the most heartbreaking infidelity in Grey’s Anatomy history – but Derek cheating on Meredith was the least believable, and it ended her marriage.

Grey's Anatomy Poster

A high-drama medical series centred on the life of Meredith Grey and her fellow doctors at Grey Sloan Memorial, who heal a multitude of ailments but are also often affected to their very core by personal relationships inside and outside the hospital. The healing has several intertwining storylines that explore the backstairs and primary halls of the hospital, tackling issues of power, conflict and love.

CastEllen Pompeo, Chandra Wilson, James Pickens Jr, Justin Chambers, Kevin McKidd, Jesse Williams, camilla luddington, Patrick Dempsey, Sara Ramirez, Jessica Capshaw, Sandra Oh.

Characters: Dr Meredith Grey, Dr Miranda Bailey, Dr Richard Webber, Dr Alex Karev, Dr Owen Hunt, Dr Jackson Avery, Dr Jo Wilson, Dr Derek Shepherd, Dr Callie Torres, Dr Arizona Robbins, Dr Cristina Yang.

Release DateMarch 27, 2005

Seasons21

Creator(s)Shonda Rhimes , Michelle Lirtzman

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21 thoughts on “Grey’s Anatomy – 14 Worst Times A Character Cheated, Ranked

  1. I still can’t get over George cheating on Callie with Izzie. It felt so out of character and unnecessary!

  2. Derek’s kiss with Renee was such a low point for his character. After all he’d been through with Meredith, it was disappointing to see him stray, even if just for a moment.

  3. Owen’s infidelity with a random woman after Cristina’s abortion felt like a betrayal to the fans who rooted for their relationship

  4. Addison cheating on Derek with Mark was such a pivotal moment in the series, setting off a chain of events that shaped Meredith and Derek’s entire relationship.

  5. Alex leaving Jo for Izzie was such a controversial move by the writers. It felt like a regression in his character development, especially after everything he and Jo had been through.

  6. Teddy’s affair with Tom while being with Owen was heartbreaking. It was like watching a trainwreck in slow motion.

  7. The emotional affair between Jackson and April that lingered even after his relationship with Maggie was tough to watch. It was clear his heart was always with April.

  8. Arizona cheating on Callie with Lauren felt like the final nail in the coffin for their relationship. It was hard to watch them fall apart after all they had been through.

  9. Ellis Grey’s affair with Richard Webber had such a lasting impact on Meredith’s life, it’s no wonder she had so many issues with relationships.

  10. Owen cheating on Emma with Cristina was a low blow, especially since he and Emma seemed so happy together. The writers really knew how to stir the pot!

  11. Richard cheating on Adele with Ellis was heartbreaking. Adele deserved so much better, and it was tough seeing her suffer because of his choices.

  12. Nathan Riggs cheating on Megan years before she went missing added another layer of complexity to his character. It was a tough pill to swallow.

  13. Izzie catching Alex with Olivia was one of the most gut-wrenching moments early in the series. It showed just how flawed Alex was back then.

  14. Derek cheating on Addison with Meredith, and then cheating on Meredith with a kiss, really showed how complicated his character was. Love isn’t always black and white.

  15. The affair between Teddy and Tom was such a mess. It felt like the writers were trying too hard to create drama at the expense of character consistency.

  16. George cheating on Callie was one of the most painful storylines. He was always portrayed as such a good guy, which made his actions even more shocking.

  17. Watching the aftermath of Derek’s kiss with Renee was brutal. It’s hard to forget the tension that hung over Derek and Meredith’s relationship afterward.

  18. Watching the aftermath of Derek’s kiss with Renee was brutal. It’s hard to forget the tension that hung over Derek and Meredith’s relationship afterward.

  19. Cristina and Owen’s relationship was so complicated, and his one-night stand just added to the heartbreak. They never seemed to catch a break.

  20. Ellis Grey and Richard Webber’s affair was a major bombshell that had repercussions throughout the series. It’s no wonder Meredith struggled with trust issues.

  21. Grey’s Anatomy never shied away from showing the messy side of relationships, and this list perfectly captures the heartbreak and drama that came with these betrayals

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