Jamie Foxx, Tom Cruise and More of the Men Lucky Enough to Have Loved Katie Holmes

Katie Holmes‘ romantic life has been star-studded in the past few decades — find out which Hollywood men were lucky enough to love her.

Joshua Jackson

In 1997, Katie fell for her Dawson’s Creek costar, later telling Rolling Stone, per Cosmopolitan, the actor was “my first love.” Though they had “something so incredible and indescribable,” they amicably split after the first season and remained friends during the show’s run.

Chris Klein

“We were like the prom king and queen,” the American Pie actor, 47, previously told People of his five-year early-2000s relationship with the actress. After bonding over their “similar upbringing” and early Hollywood experiences, they got engaged in 2003 but split by early 2005.

Tom Cruise

According to The Hollywood Reporter, in 2004, Katie told Seventeen her childhood dream was “to marry Tom Cruise.” Two years later, she and the action star exchanged vows in Italy following a whirlwind romance that began just weeks after she ended things with Chris. Katie filed for divorce in 2012.

Jamie Foxx

For six years, Katie and Jamie were Hollywood’s most elusive pair, navigating an ultra-private long-distance romance. They finally went public as a couple at the 2019 Met Gala in coordinating purple looks. But just a few months later, it was over.

Emilio Vitolo Jr.

After Jamie, Katie was far less private with Emilio, 38, an Italian chef and restaurateur. Their COVID quarantine-era romance lasted for eight months in 2020 and 2021, with the pair becoming a fixture at his family’s eatery, Emilio’s Ballato, in NYC’s SoHo neighborhood.

Bobby Wooten III

For most of 2022, Katie dated the 37-year-old Grammy-nominated composer, producer and bassist known for his work on Broadway shows including Moulin Rouge! She and the associate professor at NYU’s Tisch School of the Arts called it quits that December.