Ryan Seacrest And Shayna Taylor's Relationship Timeline

Ryan Seacrest is one of Hollywood's most eligible bachelors, but not long ago, he seemed dedicated to his future with model and chef Shayna Taylor. Before calling it quits with Taylor, 29, for a third time in 2020, the 46-year-old "Live! With Kelly and Ryan" and "American Idol" host enjoyed a years-long relationship with her, which was frequently documented on social media and discussed with his "Live!" co-host and friend Kelly Ripa. So, what went wrong between them?

Let's start from the beginning. According to a report from GBF, Seacrest and Taylor, who People revealed met through mutual friends, struck up a romance in March 2013 and continued to date on and off for over five years. However, as the People report explained, it was far from smooth sailing from there. Following a brief split in 2014, Seacrest and Taylor rekindled their relationship, and in 2017, they took a major step by moving into Seacrest's home in New York City. Then, less than two years later, they called it quits for a second time.

Ryan Seacrest and Shayna Taylor couldn't 'get it right'

After reassuring their fans and followers that they would remain friends after their second breakup in February 2019, via People, Ryan Seacrest and Shayna Taylor reunited yet again that summer. By September, after a romantic getaway aboard a yacht in Positano, Italy, it was confirmed that they were back on. Following the reconciliation, Seacrest opened up about their "roller coaster" relationship on "Live!"

"I just want to say, happy third anniversary to Shayna," he said. "It is our third time together. So we've gotten together, broken up, gotten together, broken up. This is number three of being together. So we're celebrating as well."

"Listen, nothing's perfect," Seacrest added. "You just keep trying until you get it right." Unfortunately, Seacrest and Taylor ultimately could not "get it right," and in June 2020, his representative confirmed their split. "Ryan and Shayna decided to end their romantic relationship amicably some time ago," the rep said. "They remain good friends, each other's biggest supporters and will always cherish their time together as a couple."