Bradley Cooper has been romantically linked with some of Hollywood’s biggest stars over the years, from Cameron Diaz to Renée Zellweger to Olivia Wilde.

The Oscar nominee has only walked down the aisle once, getting engaged to actress Jennifer Esposito in October 2006. The pair tied the knot that December, but their union ended up being short-lived as Esposito filed for divorce in May 2007. She and Cooper were legally single by the end of that year.

In addition to notable relationships with Zoe Saldana and Suki Waterhouse, Cooper famously dated model Irina Shayk from 2015 to 2019. The pair welcomed a daughter together, Lea De Seine, in 2017 and have become friendly coparents.

“They’ll coordinate to make sure their daughter is always with one parent,” a source exclusively told Us Weekly after the split. “When Lea has important events in her life, both Bradley and Irina will be there.”

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Scroll down to look back at Cooper’s star-studded dating history:

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