Katie Holmes is the picture of bliss as she walks

Katie Holmes is the picture of bliss as she walks around NYC after strolling with new man Bobby Wooten III

Emilio Vitolo Jr.: September 2020 – May 2021

Katie Holmes confirmed her romance with New York restaurateur Emilio Vitolo Jr. after she was spotted making out with him in September 2020.

At the time of their romance, Katie was 41 while Emilio was 33, and the couple made headlines after she sat on his lap as they had dinner at Peasant Restaurant in Manhattan, New York.

“There was no drama,” a source told PEOPLE at the time. “It was amazing while it lasted, but they are in very different places in life. Emilio doesn’t have hard feelings. His life takes place in NYC. Katie can’t wait to get back to work and travel again.”

Romance: Katie Holmes confirmed her romance with New York restaurateur Emilio Vitolo Jr. after she was spotted making out with him in September 2020

Romance: Katie Holmes confirmed her romance with New York restaurateur Emilio Vitolo Jr. after she was spotted making out with him in September 2020

Jamie Foxx: 2013 – May 2019

Holmes reportedly began dating Foxx in 2013, a year after her marriage to Tom Cruise, when they were spotted being quite flirty with each other.

While Holmes and Foxx never publicly addressed their relationship, there have been rumors that they were dating and kept their romance a secret.

They started showing more public displays of affection in 2017, and there were rumors that wedding bells might be in the works.

They eventually made their red carpet debut together at the Met Gala in May 2019, though they reportedly split shortly after the party in New York City.

Flirty: Holmes reportedly began dating Foxx secretly in 2013, a year after her marriage to Tom Cruise, when they were spotted being quite flirty with each other

Flirty: Holmes reportedly began dating Foxx secretly in 2013, a year after her marriage to Tom Cruise, when they were spotted being quite flirty with each other

PDA: You started showing more public displays of affection in 2017, and there were rumors that wedding bells might be in the works

PDA: You started showing more public displays of affection in 2017, and there were rumors that wedding bells might be in the works

Split: They eventually made their red carpet debut together at the Met Gala in May 2019, though they reportedly split shortly after the party in New York City

Split: They eventually made their red carpet debut together at the Met Gala in May 2019, though they reportedly split shortly after the party in New York City

Tom Cruise: April 2005 – June 2012

Holmes began dating Tom Cruise in April 2005, beginning a whirlwind romance that moved pretty quickly.

Just two months later, Holmes had converted from the Catholic Church to the Church of Scientology, of which Cruise had been a long-time member, and they got engaged at the Eiffel Tower in Paris later that month.

The couple’s daughter, Suri, was born on April 18, 2006, the one-year anniversary of their first date, and they married in November 2006.

Holmes filed for divorce in June 2012 while Cruise was filming a film in another country, claiming she feared Cruise and others in Scientology would kidnap her daughter Suri

Dating: Holmes began dating Tom Cruise in April 2005, beginning a whirlwind romance that moved pretty quickly

Dating: Holmes began dating Tom Cruise in April 2005, beginning a whirlwind romance that moved pretty quickly

Married: The couple's daughter, Suri, was born on April 18, 2006, the one-year anniversary of their first date, and they married in November 2006

Married: The couple’s daughter, Suri, was born on April 18, 2006, the one-year anniversary of their first date, and they married in November 2006

Suri and Katie: The couple's daughter, Suri, was born on April 18, 2006, the one-year anniversary of their first date, and they married in November 2006

Suri and Katie: The couple’s daughter, Suri, was born on April 18, 2006, the one-year anniversary of their first date, and they married in November 2006

Chris Klein – 2000 to 2005

Holmes and Klein began dating in 2000, and they became engaged in 2003, although it was mostly long-distance.

Holmes spent most of her year in North Carolina filming her hit series Dawson’s Creek during the romance.

The actress moved to Los Angeles in 2003 to be with Klein after Dawson’s Creek went off the air, but they called it quits in early 2005, though they reportedly still remain friends.

Engaged: Holmes and Klein began dating in 2000, and they got engaged in 2003, though it was mostly long-distance

Engaged: Holmes and Klein began dating in 2000, and they got engaged in 2003, though it was mostly long-distance

North Carolina: Holmes spent most of her year in North Carolina filming her hit series Dawson's Creek during the romance

North Carolina: Holmes spent most of her year in North Carolina filming her hit series Dawson’s Creek during the romance

Still friends: The actress moved to Los Angeles to be with Klein in 2003 after Dawson's Creek went off the air, but they called it quits in early 2005, though they reportedly still remain friends

Still friends: The actress moved to Los Angeles to be with Klein in 2003 after Dawson’s Creek went off the air, but they called it quits in early 2005, though they reportedly still remain friends

Joshua Jackson: 1998-1999

Holmes was cast in her breakthrough role as Joey Potter on Dawson’s Creek in 1997, and she began dating her co-star Joshua Jackson in 1998, the year the show debuted.

The couple reportedly dated for about a year, with life imitating art ever since Jackson starred in the hit series Holmes’ Boyfriend.

They reportedly split sometime in 1999, though they both starred in all six seasons of Dawson’s Creek before it went off air in 2003.

Breakthrough: Holmes was cast in 1997 for her breakthrough role as Joey Potter on Dawson's Creek, and she began dating her co-star Joshua Jackson in 1998, the year the series debuted

Breakthrough: Holmes was cast in 1997 for her breakthrough role as Joey Potter on Dawson’s Creek, and she began dating her co-star Joshua Jackson in 1998, the year the series debuted