Justin Timberlake's Loves & Hookups

Justin Timberlake started dating Jessica Biel in January 2007, and later became engaged in December 2011.

On October 19, 2012, Timberlake married Biel at the Borgo Egnazia resort in Fasano, Italy. Their son, Silas Randall Timberlake, was born in April 2015. 

In July 2020, it was reported that the pair welcomed their second son, after a top secret pregnancy. A friend confirmed the news to Daily Mail, though neither star has commented on the newborn yet.

Jessica Biel rose to fame in the late '90s, thanks to her role as Mary Camden in the hit television series 7th Heaven. Since then, she has established a successful career in film with notable roles in movies such as The Texas Chainsaw Massacre, The Illusionist, and Total Recall. Aside from her acting career, she is also well-known for her philanthropic work and has founded several organizations devoted to the well-being of children. In regards to her romantic history, Jessica Biel has been linked to actors Chris Evans and Derek Jeter before settling down with Timberlake.

Justin Timberlake and Olivia Wilde sparked dating rumors in 2011 when they were spotted getting cozy at an SNL after-party following Timberlake's appearance on the show. Although both parties denied the romance, they did share the screen in the science fiction film In Time. It was speculated that their closeness on set might have led to the rumors; however, their relationship was never confirmed, and both have moved on to other partners. The flirtation was brief, but it certainly turned heads while it lasted.

Olivia Wilde initially gained fame by playing Alex Kelly in the teen drama The O.C. before landing her breakthrough role as Dr. Remy Thirteen Hadley in the hit medical series House M.D. She has continued to maintain a successful career in both television and film, landing major roles in movies like Tron: Legacy, Cowboys & Aliens, and Rush. Apart from her acting career, Wilde is an advocate for several charitable organizations and actively uses her platform to bring awareness to important causes. In her personal life, she was previously married to Italian aristocrat Tao Ruspoli before finding love again with actor and comedian Jason Sudeikis, with whom she shares two children.

In April 2011, tabloids speculated that Justin Timberlake had a brief fling with actress Olivia Munn while he was on a break from his now-wife Jessica Biel. Though it was a short-lived romance, the two reportedly met at a MySpace party and exchanged numbers after hitting it off. Neither party ever confirmed the rumors, and their alleged relationship seemed to fizzle out as quickly as it began. It remains one of many Hollywood romances that may have happened but were never officially recognized.

Olivia Munn made a name for herself as a television personality, co-hosting G4's Attack of the Show! from 2006 to 2010 before breaking into acting with roles in television and film. She's best known for her roles as Sloan Sabbith in the HBO series The Newsroom and Psylocke in the movie X-Men: Apocalypse. She has also authored a memoir titled Suck It, Wonder Woman!: The Misadventures of a Hollywood Geek. As far as her love life goes, Olivia Munn has been previously linked to famous men such as Aaron Rodgers, Chris Pine, and most recently, comedian John Mulaney.

Rumors of a romantic link between Justin Timberlake and Lindsay Lohan began swirling in 2009 after the pair were spotted partying together at a New York club. The two reportedly shared a few intimate moments, but the alleged fling never developed into anything serious and seemed to have been just a brief encounter amid the Hollywood party scene. Both Timberlake and Lohan have remained tight-lipped about their rumored dalliance, and it remains one of the many unconfirmed relationships in Tinseltown.

Lindsay Lohan burst onto the Hollywood scene as a child actress, starring in films like The Parent Trap, Freaky Friday, and Mean Girls. Unfortunately, her career took a nosedive due to personal struggles and multiple run-ins with the law. Despite her setbacks, Lohan has continued to work in the entertainment industry, with recent projects including a reality show, Lindsay Lohan's Beach Club and a role in the supernatural thriller Cursed. In terms of her romantic life, Lohan's high-profile relationships include hookups with Wilmer Valderrama, Samantha Ronson, and most recently, Egor Tarabasov.

In 2009, Justin Timberlake collaborated with Rihanna on the sultry track "Rehab," and their undeniable chemistry sparked rumors of a romance brewing between the two artists. Although neither confirmed the relationship, they were spotted getting close at an industry event in Los Angeles. However, the flame seemed to fizzle out quickly, and they both went on to pursue other romantic interests. Regardless of their short-lived flirtation, they continue to respect each other as musicians and colleagues.

Rihanna, a Barbadian singer, songwriter, and entrepreneur, rose to fame with her debut album Music of the Sun and quickly became a global sensation thanks to hit singles like "Umbrella," "Diamonds," and "Work." Apart from her music career, she has successfully launched her fashion and cosmetics lines, Fenty Fashion and Fenty Beauty. As for her personal life, Rihanna has been romantically linked to several high-profile men, including Chris Brown, Drake, and most recently, billionaire Hassan Jameel.

Speculation arose in 2007 that Justin Timberlake and Scarlett Johansson were an item after collaborating on Timberlake's "What Goes Around... Comes Around" music video. The undeniable chemistry between the two was palpable both on and off-screen, leading many to believe the couple was secretly dating. However, the rumored romance seemed to be just that -- a rumor -- as both parties maintained their friendship without ever confirming a relationship. Nevertheless, their flirtation left many wondering what could have been.

Scarlett Johansson is a highly acclaimed actress with an impressive filmography that includes roles in movies like Lost in Translation, The Avengers franchise, and Marriage Story. She has earned multiple award nominations for her performances and holds the title of the world's highest-paid actress. In addition to her acting career, Johansson has also dabbled in music and philanthropy. While her romantic history includes relationships with fellow actors Ryan Reynolds and Sean Penn, she is currently happily engaged to Saturday Night Live writer and comedian Colin Jost.