Although Richard seemed to be physically recovering in the finale of his 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.
If Addison was just a little bit older or Richard a little bit younger, these two would have been a cute couple.
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.
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.
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