Richard Webber has always been the moral center of Grey’s Anatomy — the steady voice in the operating room, the teacher who shaped generations of surgeons, and the man who believes deeply in loyalty and responsibility. But when it comes to love, Richard’s life has been anything but simple. Across the decades, his romantic relationships have exposed his deepest flaws, greatest regrets, and quiet hopes for redemption.

From forbidden love to lifelong partnership, Richard’s love story is one of Grey’s Anatomy’s most layered and underrated arcs.

Ellis Grey: The Love That Changed Everything

Ellis Grey was not just Richard’s great love — she was the one who altered the course of his life forever. Their affair during their residency was intense, brilliant, and deeply destructive. Together, they pushed each other to be better surgeons, but neither had the courage to leave their marriages at the right time.

Ellis chose ambition and motherhood over Richard. Richard chose stability and Adele. The cost was enormous. Ellis carried the emotional fallout for decades, while Richard lived with constant guilt — guilt that shaped how he treated Meredith, how he viewed mentorship, and how he punished himself emotionally long after Ellis was gone.

Ellis was the love Richard wanted — and the one he believes he failed.

Adele Webber: The Love He Took for Granted

If Ellis was passion, Adele was patience. Adele stood by Richard for years — through late nights, broken promises, alcoholism, and emotional distance. She loved him fiercely, even when he gave her very little in return.