Addison Forbes Montgomery was the first character to shake up Grey’s Anatomy. The narrative — and Kate Walsh’s portrayal of the character — in Season 1 quickly encouraged fans to root for Addison instead of deeming her a villain. She continually won people over with her incredible surgical skills and prickly yet lovable personality, to the point where Addison’s story became bigger than Grey’s Anatomy could contain. Thus, the spinoff Private Practice was born.

Private Practice followed Addison after moving to Los Angeles to do something for herself and something outside of her now-iconic love triangle with her ex-husband Derek and the now-partially-departed Meredith Grey. She worked at Seaside Health & Wellness Center (originally Oceanside Wellness) with a group of coworkers who became more than that over the years. One such colleague was Derek’s little sister Amelia Shepherd, who joined Private Practice in its third season. Amelia and Addison’s relationship was close; they became sisters themselves. This was all while Addison faced several challenges, started the family she’d always wanted and found a new love of her life.

Addison Montgomery’s Complicated Life on Private Practice

Addison joined Seaside Health & Wellness Center after a backdoor pilot crossover on Grey’s Anatomy, in which she reunited with her former best friend Naomi Bennett and her group of doctors at the Los Angeles practice. Addison’s initial intentions were to have a baby with the help of a sperm donor, as her relationship with both Derek and Mark Sloan fell through. But she was riddled with fertility complications, making it difficult for her to conceive a child.

Addison accepts a position at the practice, but in typical Shondaland fashion, her personal and work lives intermix with each other and cross many boundaries. Throughout the series, she becomes involved in not only one but two love triangles. The first of which is between Sam, Naomi’s ex-husband, and Pete Wilder, an alternative medicine specialist. The second of which came after Pete’s death when Addison is forced to choose between Sam and a reproductive endocrinologist and infertility specialist, Jake Reilly. Her relationship with Sam always appeared to be an endgame, considering he was a consistent choice for Addison. But the one thing she wanted in life was children, which Sam was unwilling to give her. Jake, on the other hand, had adopted his former wife’s daughter and was a family man through and through.

Addison Montgomery Fast Facts

• Addison Montgomery joined Seaside Health & Wellness Center to help her friends build their business.
• Addison becomes wrapped up in two love triangles throughout the series, with the idea of having a family in mind.
• Amelia and Addison’s relationship was always a point of tension due to Amelia’s reliance on drugs.

As she dealt with infertility issues and chooses between several men, Addison also had problems with her friendships. Private Practice excelled at depicting the complexities of female friendships by illustrating dynamic women. Addison and Naomi had an on-and-off relationship due to their differing beliefs about abortion and Addison’s relationship with Sam. When Amelia broke sobriety and went missing for a few days, Addison’s internal love and hate for Amelia battled with each other. Addison wanted to help Amelia, but the latter’s unwillingness to get sober became a roadblock Addison found difficult to pass. The relationship between Addison and Amelia was the true Montgomery-Shepherd love that Addison deserved after all.

Addison Montgomery’s Husband Helped Her Find Her Happy Ending

• Addison was able to close the door on her failed relationships when she adopted a son and married Jake Reilly.
• Amelia and Addison found peace in their relationship by accepting that sisters have their bad moments.

But the real love that Addison found on Private Practice was with Jake Reilly. The beginning of their romance had some rom-com tropes, especially their meet-cute in a grocery store, but the couple ended up living happily ever after with an adopted son named Henry. Addison met her match in Jake, and he earned an extra gold star by being there for Amelia during some of the most challenging times in her life. But when the series ended in 2013 and Amelia moved to Grey’s Anatomy as a recurring character, fans began waiting for Addison’s return to Grey Sloan.

Addison came back in Season 18 before becoming a recurring character in Season 19, and her reunion with Amelia was enough to bring tears to even a casual fan’s eyes. To call Addison and Amelia’s dynamic a friendship is the understatement of the century; their sisterhood was sharply defined even before Amelia interacted with her brother Derek. Addison and Amelia’s bond was far more profound than anyone may have realized, especially if viewers were only seeing their connection on Grey’s Anatomy.

Grey’s Anatomy Didn’t Ignore Addison’s Journey

Meredith and Addison Talk About Derek – Grey’s Anatomy

Upon Addison’s return in the Season 18 episode “Hotter Than Hell,” fans were apprehensive that Grey’s Anatomy might attempt to stir the pot again and add more drama to Addison’s life. She returned to Grey Sloan Memorial to perform a uterine transplant and was immediately met with unfamiliar faces. The residents thought of her as a legend around these parts whose story only revolves around the infamous love triangle.

The Addison-Derek-Meredith love affair was a story told through generations in the hospital, but nobody had the correct details to do it justice. After she performed the surgery and was confronted by so many references to the now-deceased Derek, she broke down in the elevator with Meredith. She didn’t feel Derek in the hospital anymore and feels he’d disappeared into the void. But Meredith reassured her that Derek’s presence was still there through her children, whom she introduced Addison to.

In terms of her reunion with Amelia, the series reinforced Addison’s happy ending by maintaining her meaningful relationship with Amelia — which also proved the long-running medical drama wouldn’t be hurt if it incorporated more Private Practice characters like Charlotte King in its future, especially now that Ellen Pompeo has temporarily departed the series. Most importantly, Addison’s reappearance reinforced that happy endings are possible since they’re subjective.

Grey’s Anatomy Brought Addison’s Journey Full Circle

• Addison returned to Grey’s Anatomy in Season 18 to perform a uterine transplant.
• As the residents spread gossip about Addison and Meredith’s past feud, Addison was overwhelmed by Derek’s lack of spirit in the hospital.
• By giving her closure on Derek’s death and reaffirming the love between Addison and Amelia, Grey’s Anatomy let Addison keep her happy ending.

Grey’s Anatomy is about the journey, and sometimes that journey can be heartbreaking, tedious and possibly go on too long. But certain special people can make it worthwhile. Addison’s family with Jake and Henry established on Private Practice is a part of her happily ever after, but so is her sisterhood with Amelia that continued on Grey’s Anatomy. It’s reflected in their ability to say big, sometimes scary things that embrace imperfections. Addison created a safe space for Amelia to candidly express what she wanted for herself for the first time. Grey’s Anatomy also gave Addison a chance to find closure with Derek by seeing his spirit live on in his children.

Happy endings look different to everyone, and sometimes they evolve and become something new. Addison’s ending will likely continue to change, but her relationship with Amelia is a constant for Addison and vice versa. It’s a joy to see Grey’s Anatomy revisit and strengthen that bond years later.