While some stars will spend Valentine's Day with their significant other, celebrities like Jennifer Aniston will be celebrating the holiday solo. However, she wasn't always a single lady.

Take a look back at Aniston's dating history and check out some of her most high-profile relationships below.

Brad Pitt (1998 - 2005)

Brad Pitt and Jennifer Aniston
3. Brad Pitt and Jennifer Aniston - These two were the “it” couple in the late 90’s -- Brad Pitt was one of the biggest Hollywood stars at the time, while Jennifer Aniston was labeled as America’s sweetheart. Hence, the media couldn’t get enough of how good-looking the couple was. They went public with their relationship at the 1999 Emmy Awards red carpet. After a year of dating, they had a Malibu-beach wedding. Both have been quite open about professing their love for each other in front of the media. However, after seven years of being together, Aniston filed for divorce in 2005 due to “irreconcilable differences.” It became a crazy breakup after Pitt went public with his then relationship with Angelina Jolie shortly after. The two stars met on the set of 2005's "Mr. & Mrs. Smith," a movie they filmed while Pitt was still with Aniston. Pitt and Jolie have also decided to divorce in 2016. Kevin Winter/ Getty Images

After dating for two years, Aniston and Pitt were married from 2000 to 2005 and were essentially Hollywood's "It" couple. Fans were shocked when Pitt moved on to his "Mr. and Mrs. Smith" co-star Angelina Jolie, shortly after separating from Aniston.

Vince Vaughn (2005 - 2006)

Actor Vince Vaughn
Actor Vince Vaughn REUTERS/Lucas Jackson

The same year she separated from Pitt, Aniston began dating Vaughn, her co-star in the 2006 film "The Break-Up." Similar to their movie characters, Aniston and Vaughn's relationship didn't long. However, the "Friends" alum spoke fondly of their time together in a 2008 interview with Vogue.

"I call Vince my defibrillator," Aniston explained. "He literally brought me back to life. My first gasp of air was a big laugh! It was great. I love him. He's a bull in a china shop. He was lovely and fun and perfect for the time we had together. And I needed that. And it sort of ran its course."

John Mayer (2008 - 2009)

Jennifer Aniston
Jennifer Aniston is not getting back together with John Mayer. Pictured: Jennifer Aniston and singer John Mayer arrive at the Vanity Fair Dinner and After Party celebrating the 81st Academy Awards at the Sunset Tower Hotel in West Hollywood, California on February 22, 2009. Rags-to-riches drama 'Slumdog Millionaire' swept the board at the 81st Academy Awards, winning eight Oscars including best picture on a night of high-voltage Hollywood glamor. Getty Images/Rich Schmitt

Aniston couldn't resist getting entangled with the Hollywood serial dater known as John Mayer. After meeting at an Oscars party, the two had an on-and-off relationship that eventually ended. In 2010, Mayer hinted that Aniston may have been the one who got away.

"I've never really gotten over it. It was one of the worst times of my life," Mayer told Rolling Stone.

Justin Theroux (2011 - 2018)

Justin Theroux, Jennifer Aniston
Justin Theroux (L) and Jennifer Aniston (R) pose during a photocall ahead of a diner for the launch of a Louis Vuitton leather goods collection in collaboration with US artist Jeff Koons, at the Louvre in Paris on April 11, 2017. Getty Images/Gabriel Bouys

Aniston appeared to find her love match when she began dating Theroux after meeting him while working on the film "Wanderlust." After getting engaged in 2012, Aniston and Theroux tied the knot in 2015. By 2018, the couple announced their separation in a joint statement.

"We have decided to announce our separation. This decision was mutual and lovingly made at the end of last year. We are two best friends who have decided to part ways as a couple, but look forward to continuing our cherished friendship," the statement read.

What The Future Holds

GettyImages-1200777248
59. Jennifer Aniston - An American actress, producer, and businesswoman, Jennifer Aniston started working in the industry at a young age with an uncredited role in the 1987 film Mac and Me. She later became a household name after starring as Rachel in the sitcom Friends. Aniston is now one of the biggest stars in Hollywood who famously married and divorced Brad Pitt. Jason Merritt/Getty Images

While Aniston is open to dating again, she doesn't see marriage in her future. "Never say never, but I don't have any interest," she told Allure for her December 2022 cover story.

"I'd love a relationship. Who knows? There are moments I want to just crawl up in a ball and say, 'I need support.' It would be wonderful to come home and fall into somebody's arms and say, 'That was a tough day.'"

Read more
Brad Pitt