After Simpson and Cobb hit it off in the early 2000s, Cobb quickly became the musician’s personal assistant and bestie. The former Columbia Records employee even moved in with Simpson and then-husband Nick Lachey while filming season 2 of Newlyweds in 2004.
While fans of the reality show saw their closeness, Simpson revealed in her 2020 memoir, Open Book, that the pals had a falling out after Cobb didn’t approve of Simpson’s decision to leave Lachey — or how quickly she moved on with John Mayer.
“CaCee felt uncomfortable with my decision to date John. I always saw CaCee as my friend first, but she was always very professional as well. John was a Columbia artist, and she knew John from before he was even signed,” Simpson wrote. “She had already been put in the middle of the situation with Nick and she didn’t want to go through that again. But CaCee was also uncomfortable with a lot of my decisions back then.”
According to Simpson, Cobb quit being her assistant not long after she started seeing Mayer. “I’d grown so dependent on her that it felt like she was leaving me,” she wrote. “I felt abandoned. Our friendship was strained for quite some time.”
Simpson and Cobb found their way back to each other in 2008 when the fashion designer asked Cobb to help her with her country album.
“I thought I had failed her in my divorce,” Simpson wrote in Open Book. “She had come in and out of my life around John, and I thought I had broken her heart when I left Nick.”
In 2012, the ladies proved to be closer than ever with Simpson acting as the maid of honor in Cobb’s wedding to Donald Faison.
“I was the maid of honor last night for my BF @caceecobb. She was the most beautiful bride I have ever seen in my life!” Simpson tweeted at the time.
Two years later, Cobb stood by Simpson’s side at her 2014 nuptials to Eric Johnson.
Scroll through to see how these Hollywood besties have stood by each other through the ups and downs: