Inside Katie Holmes's Incredibly Secretive Dating History

The "Dawson's Creek" costars reportedly dated during season one of their hit show in 1998. During an interview with Rolling Stone that year, the actor said that Jackson was her "first love." It's unclear when exactly the former pair split, but they remained friends throughout their TV show's six-season run.

Holmes and Klein started dating in 2000 when the former was still on "Dawson's Creek." They got engaged three years later. After five years of dating, People reported that the two called off their engagement when they broke up in March 2005.

The duo certainly had a whirlwind romance. Nearly a month after calling off her engagement to Klein, Holmes made her relationship with Cruise public by appearing with him in Rome. In June 2005, the "Coda" actor converted from Catholicism to the Church of Scientology, and a month later, the former couple announced their engagement.

In April 2006, they welcomed their daughter, Suri, and later that year, they made things official by tying the knot during a lavish wedding in Bracciano, Italy. After five years of marriage, People reported that Holmes filed for divorce in June 2012. Their divorce was settled 10 days later with custody of their daughter going to Holmes.

While the pair met when Holmes was still dating Cruise, their relationship didn't turn romantic until almost a decade later when they were spotted dancing together at a star-studded Hamptons party in August 2013. After keeping their relationship under wraps for about three years, Foxx and Holmes made their first official outing as a couple at Clive Davis's annual pre-Grammys bash in January 2018.

Following six years of dating, Us Weekly confirmed the pair's breakup in August 2019. Despite so many years together, a source previously told the outlet that Holmes and Foxx had no plans to get married, while another explained their reasoning was because they didn't want to "disrupt either of their families."

Holmes and Vitolo Jr. were first linked in September 2020, showing off a little PDA during some of their romantic dates around New York City, Entertainment Tonight reported. Two months later, the former couple made their relationship Instagram official on Holmes's birthday after Vitolo Jr. gave the actor a sweet shoutout in a now-deleted post, marking the first time the two publicly acknowledged their romance.

They celebrated Valentine's Day together in February 2021, and Holmes posted a bouquet of red roses on Instagram with Vitolo Jr. tagged. However, in May 2021, a source confirmed the pair's split to People, noting "they are at very different places in life."

In April 2022, People posted photos of Holmes and Wooten III kissing and holding hands in New York City, confirming their romance. Since then, the two have been low-key about their relationship, but they were spotted showing off some PDA on another casual NYC date in May 2022. They also stepped out for their red carpet debut as a couple that same month when they attended the Moth Ball's 25th anniversary gala.

On June 14, the two proudly showed up to the Tribeca Film Festival's red carpet for the premiere of Holmes's new film, "Alone Together." The pair held each other close as they posed for cameras. Neither Holmes nor Wooten III has spoken out about their relationship yet, but it seems like they're letting their couple pictures do all the talking.