John Mulaney and Anna Marie Tendler pulled the plug on their marriage after nearly seven years of marriage — and fans didn’t see it coming.

The duo tied the knot in July 2014 in upstate New York with several of Mulaney’s former Saturday Night Live coworkers in attendance. “On a beautiful and perfect day, I married a beautiful and perfect woman,” Mulaney gushed via Instagram one day after the nuptials. “I wish I could live it over and over again.”

Six years later, news broke in December 2020 that Mulaney voluntarily checked into a rehab facility seeking help for drug and alcohol addiction. Prior to relapsing, Mulaney was sober for over a decade.

Mulaney left the Pennsylvania treatment center after 60 days, continuing recovery in an outpatient program. His marriage, however, continued to suffer, and in May 2021, Us confirmed that Mulaney and Tendler split two months shy of their seven-year anniversary.

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As news of his breakup made headlines, Mulaney moved on with Olivia Munn, with whom he now shares two children.

Scroll down for a look back at Mulaney’s relationship with Tendler: