Grey’s Anatomy: 10 People Richard Should Have Ended Up With (Other Than Catherine)

Although Richard seemed to be physically recovering in the finale of Grey’s Anatomy, his marriage to Catherine remains as broken as ever. Ever since he was fired from Grey-Sloan, their relationship hasn’t been the same since. The couple even announced they were separating after Catherine maliciously bought and closed down the hospital he worked at to spite him.

Fans feel that Webber deserves better, especially since the urologist is continuously trying to undermine and control his career at every turn. But who would be a more suitable match for the Chief? From Carol Shepherd to Gemma Larson, here are 10 people Richard should have ended up with instead of Catherine.   

Addison Montgomery

If Addison was just a little bit older or Richard a little bit younger, these two would have been a cute couple. As many fans know, Webber always had a soft spot for Addison. He was the first person to let her know where Derek was and updated her about Meredith.

Addison and Webber also forged a friendship in the aftermath of his split with Adele, where the OB/GYN helped to get his life on track. If the writers didn’t go down the mentor-mentee route, they could have found comfort in each other.

Evelyn Hunt

Another person Richard could have been matched with was Owen’s mother, Evelyn. Although Evelyn has only appeared in 9 episodes, fans have learned a lot about her life. They know that she served in the Vietnam War and had been a scrub nurse at some point in her life.

She also revealed that their family had lived five miles from Grey-Sloan, meaning she could have run into Richard at some point. Since Richard has been looking for something to fill the void Adele left, maybe he could have met Evelyn in the writing class instead of John.

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Carolyn Shepherd

How funny would it be if Richard and Carolyn got together in the early stages of the show? Do the writers not realize what comedy gold they could have had if Derek found out Webber was dating his mother? Now that the idea is planted, here are a couple of reasons why these two should have been matched.

For one, they both understand what it’s like to lose someone they truly loved. Two, Carolyn was also a navy nurse for 25 years so she would have understood the pressures of the job. Three, they deserve their own happiness after spending years putting other people’s needs ahead of their own.

Marie Cerone

Although Marie and Webber never shared any screen time, it was clear from his discussions with Meredith that he knew her. In fact, they came across each other more than once since she was Ellis Grey’s best friend. While Ellis’ journals suggest Marie thought Richard was a distraction from work, what if Marie’s vendetta was for a different reason.

Instead of an affair with Ellis, what if Richard and Cerone had fallen in love but their relationship ended when she left for Spain? Then, when she returned in season 14, the writers could have allowed them to reconnect. It could have made another epic romance.

Diane Pierce

Another woman the writers could have had as a romantic interest was Diane Pierce. As many fans know, Diane was Maggie’s adoptive mother, who came to Seattle after she discovered she was terminally ill. While she was admitted to the hospital, Diane bonded instantly with Maggie’s colleagues, including Richard.

Although they only shared a couple of scenes, fans could see there was a natural chemistry. She was a kind and charming person, bringing a smile to everyone’s face. If she arrived years earlier and revealed he had a daughter, they could have raised her together.

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Gemma Larson

With Catherine and Richard separation looking permanent, could his next love interest be Gemma? It’s not as if a romance between them would be totally out of the blue since he and the accountant have already kissed. Fans have also noticed a spark between the two, especially since Gemma helped make his transition to Pac North easier.

It is important to note that Gemma and Richard have more things in common than he does with Catherine. She understands his demons because she is a recovering alcoholic. They had the same sponsor, meaning they share the same grief. Most importantly, Gemma doesn’t disrespect his career or belittle him. There could be a future here…

Miranda Bailey

Bailey and Richard sitting on a bench together

Again, if Miranda was just a little bit older or Webber was younger, they would have made quite the couple. With the staff already calling them “work husband and wife,” it’s obvious that people feel like their partnership mimics a marriage. Even Adele at one point thought they were having an affair because she recognized they had chemistry.

Adele believed the two would go to the ends of the world for each other – and she was right. Despite all the squabbles and bickering, Richard and Bailey will always be there in the darkest of times. She is his “person.”

Olive Warner

Fans may not have contemplated it, but what if Richard had fallen in love with his sponsor, Olive? Out of all the people in Richard’s life, Olive was his one constant figure. She was the one who supported him through his alcoholism the first time around.

She was also the one Richard called whenever he was going through a rough patch – talking at least three times a week. This romance could have been beneficial to Webber’s character, especially since he always looked comfortable around her.

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Ellis Grey

A flashback scene showing Ellis and Richard's happy days in Grey's Anatomy

Although she is similar to Catherine, another person Richard could have ended up with was Ellis. Richard and Ellis were another iconic love, with the couple’s romance starting when they were both in their residency. From her journals, Ellis stated it had been a passionate affair and that they were planning on starting a life together.

If Webber had known that she had been pregnant with Maggie, he would have followed her to Boston and helped raise Meredith. Even “If/Then” showed them to be happily married…

Adele Webber

Adele and Richard dancing at a wedding in Grey's Anatomy

If there was one person Richard should have ended up with, it was Adele. Every fan knows that she was the love of his life. She was always seen as a kind and considerate woman. However, she was also seen to have a fiery attitude, which always came out when she thought someone was trying to double-cross her.

Although his affair and their brief separation deeply affected their marriage, Richard and Adele still managed to find their way back to one another. It’s just a shame she got Alzheimer’s and died because Webber hasn’t been happy since.

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