Jessica Biel & Justin Timberlake’s Relationship Timeline — Photos – Hollywood Life

Justin Timberlake & Jessica Biel’s Relationship Timeline: From A Breakup To Marriage, Babies & More

In honor of Justin Timberlake's 40th birthday, we're breaking down the singer's ups and downs over the years with his wife, Jessica Biel.

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Image Credit: AP Images

Justin Timberlake and Jessica Biel might be a famed Hollywood couple, but that doesn’t mean their relationship has always been perfect. The pair have worked so hard to keep their romance alive, and like any longtime couple, they’ve had their share of ups and downs. But through it all, the two have remained absolutely steadfast! To celebrate Justin’s 40th birthday, let’s take a look back at how the couple got together and the highs and lows of their romance up to today!

When Did Justin Timberlake & Jessica Biel Start Dating?

Jessica Biel and Justin Timberlake hold hands while out and about. (SplashNews)

Jessica and Justin met in the latter half of the 2000s, potentially early 2007. Justin even opened up about asking Jessica on a date during a press conference with the Hollywood Foreign Press Association. “I had to be pretty persistent in order to get her to say yes,” Justin recalled, according to Us Weekly. “But I have a fair amount of tenacity and if I want something I stick to it. And in the end, she agreed.”

As 2007 continued, the two finally went public with their romance but rarely discussed their relationship. They were often photographed out and about together, with minimal PDA, of course. From time to time, Justin even alluded to his dating life, but never directly addressed his romance with Jessica.

Justin Timberlake & Jessica Biel Make Their Red Carpet Debut

Justin Timberlake and Jessica Biel make their first red carpet appearance together at the 2009 Met Gala. (SplashNews)

It wasn’t until 2009, two years after they met, that Justin and Jessica made their red carpet debut at the 2009 Met Gala. As seen in the photograph above, Jessica wore a stunning strapless red gown while Justin looked dapper in his tux. The two seemed to be living on Cloud Nine, although their romance was just about to hit tough chapter.

Justin Timberlake & Jessica Biel Split

Justin Timberlake and Jessica Biel arm in arm at the Met Gala. (AP)

After a few years of dating, Justin and Jessica went their separate ways in March 2011. The couple’s reps released a statement about their breakup, saying, “the two remain friends and continue to hold the highest level of love and respect for each other.” The split, however, didn’t last long. By the summer of 2011, the two were spotted out and about together once again. It’s unclear when the couple reunited, but the bonds of their relationship became so much stronger over the course of those few months, that Justin was ready to take a huge leap of faith.

Justin Timberlake & Jessica Biel Get Engaged

Justin Timberlake and Jessica Biel at Vanity Fair Oscar Party. (AP)

In December 2011, Justin proposed to Jessica while the two were in Montana. “When I did propose, I was saying to her, I was like, ‘Oh look at the shadows on the mountains,’ and I had the ring on my pinkie—I guess I will just tell the story. I had the ring on my pinkie and I was like, ‘Look at the shadows over there on the mountains,’ and she was like, ‘Oh yeah, that’s beautiful,’ and I was like, ‘Do you see it?’” Justin told Amazon Music.

Justin Timberlake & Jessica Biel Get Married

Justin Timberlake and Jessica Biel at the Emmys. (AP Images)

In October 2012, Jessica and Justin exchanged their wedding vows in picturesque Italy. Justin actually sang to Jessica as she walked down the aisle, making the moment all the more special. “It was an original piece I wrote specifically for the evening and for her,” Justin told People. Jessica wore a gorgeous Giambattista Valli Haute Couture gown and couldn’t have been happier. “It was a total fantasy experience,”  the actress said of her wedding.

Jessica Biel & Justin Timberlake Have A Baby Boy


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A post shared by Justin Timberlake (@justintimberlake)

At the end of January 2015, Justin took to Instagram and shared a sweet photo of himself kissing Jessica’s baby bump, announcing that the couple was expecting their first child after nearly three years of marriage. “Thank you EVERYONE for the Bday wishes! This year, I’m getting the GREATEST GIFT EVER. CAN’T WAIT,” he captioned the above image. In April 2015, the pair welcomed their first child, son Silas Randall.

Justin Timberlake Is Spotted Out With Alisha Wainwright 

Justin Timberlake and Alisha Wainwright at separate red carpet events. (AP)

In November 2019, Justin was photographed holding hands with his Palmer co-star Alisha Wainwright. The two were out with cast and crew members during a night off, when Justin seemingly became a bit too familiar with Alisha. Justin’s actions were incredibly scrutinized by media outlets, leading the actor and singer to finally break his silence.

“I stay away from gossip as much as I can, but for my family I feel it is important to address recent rumors that are hurting the people I love,” he began his December 4 Instagram message. “A few weeks ago I displayed a strong lapse of judgement – but let me be clear – nothing happened between me and my costar. I drank way too much that night and regret my behavior. I should have known better. This is not the example I want to set for my son.”

“I apologize to my amazing wife and family for putting them through such an embarrassing situation, and I am focused on being the best husband and father I can be,” he wrote. “This was not that. I am incredibly proud to be working on Palmer. Looking forward to continuing to make this movie and excited for people to see it.”

Following Justin’s statement, he and Jessica kept a low-profile and quietly worked on their relationship. The two were spotted out and about from time to time, but they mostly maintained their privacy. Luckily, the pair welcomed some wonderful, exciting news into their lives and put any rumors behind them.

Justin Timberlake & Jessica Biel Have Baby No. 2


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A post shared by Justin Timberlake (@justintimberlake)

Beginning in mid-2020, rumors began to circulate that Justin and Jessica had quietly welcomed their second child into the world. But it wasn’t until six months later that Justin finally confirmed the news during his appearance on The Ellen DeGeneres Show. “His name is Phineas,Justin shared with the eponymous host in January 2021. “He’s awesome, and he’s so cute. And nobody’s sleeping. But we’re thrilled. We’re thrilled, couldn’t be happier, very grateful.”