Justin Timberlake and Jessica Biel’s Rocky Relationship Timeline, From Scandal to Making it Work

Late 2006/Early 2007

Jessica said she “technically met” her husband while attending a birthday party Justin was throwing for a mutual friend. The “Cry Me a River” singer asked his pal to ask the Summer Catch actress if he could call her, which is how he asked her out on a proper date.

“I had to be pretty persistent in order to get her to say yes,” the former boyband member told the Hollywood Foreign Press. “But I have a fair amount of tenacity and if I want something I stick to it. And in the end, she agreed.”

May 2007

After being spotted snowboarding together in January 2007, the pair took their romance public after photos of them kissing during a trip to the U.K. surfaced.

January 2010

The duo stayed pretty low-key through the years. However, Jessica said their relationship was “the most precious thing that I have in my life,” during an interview with Vogue.

March 2011

Jessica and Justin hit a rough patch and called it quits. “The two remain friends and continue to hold the highest level of love and respect for each other,” their reps told People at the time.  

June 2011

There were clearly still feelings between them when Justin sat down for an interview with Vanity Fair. 
“In my 30 years, she is the most special person, OK? I don’t want to say much more, because I have to protect things that are dear to me — for instance, her,” he said about Jessica amid their split.

July 2011

Their breakup didn’t stick too long because the A-listers were seen riding bikes and eating tacos together a few months later.

December 2011

Do you hear wedding bells? Justin and Jessica *finally* got engaged during a trip to 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,” he told Amazon Music at the time.

October 2012

They had a short engagement and got married 10 months later during an intimate ceremony in Italy. We’ll forever be obsessed with Jessica’s pink wedding gown. 

April 2015

From newlyweds to parents! Jessica gave birth to their first child, Silas Randall. 

January 2017

The Valentine’s Day actress gushed over her hubby’s career during an interview with Entertainment Tonight.
“I think having a partner who is doing something that you’re excited about — like for me, his music and everything that he does — it’s just amazing to see somebody doing what they love, and I think it can be as simple as that,” she said.

January 2018

Jessica celebrated Justin’s birthday with an amazing tribute. “A picture says a thousand words. And thank goodness because there aren’t enough to express ALL the aspects of my love and respect for you,” the 7th Heaven star wrote in a sweet Instagram post.
“Here’s to a spectacular year ahead. I’m so proud of all you’ve accomplished and all that is ahead for you. plus you’re a super hot dad. A ninja dad. A kiddie teeth brushing, Jedi sleep mind tricking, intimidating dad voice disciplining SUPER HOT DAD,” she continued. “I love you, you hot dad. I’m here, right by your side, OG fan girl #1. Happy birthday, my beloved.”

February 2018

The pair reminded us that they are one of the hottest couples in Hollywood while appearing at the Emmys together. 

October 2019

A few days after admitting she was “not a huge fan” of ‘NSYNC during an appearance on The Tonight Show, Jessica stepped out on Halloween dressed as her hubby during his boy band days. Meanwhile, Justin rocked a microphone costume.
“This is what happens when you admit on TV that you don’t know any NSYNC songs and you’re married to @justintimberlake,” she wrote on Instagram. “Well played, husband, well played.”

November 2019

The “My Love” singer was photographed holding hands and looking very close with his Palmer costar Alisha Wainwright while at a bar in New Orleans in November 2019.

December 2019

The Friends With Benefits actor denied cheating accusations and assured fans that “nothing happened” with his costar while issuing a public apology to his wife and family.

“I drank way too much that night and I regret my behavior. I should have known better,” he wrote in a statement. “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. This was not that.”

March 2020

The couple seemingly weathered the storm and celebrated Jessica’s birthday. Justin called his wife the “love of my life” in an Instagram post while the Sinner star detailed her cozy day.

“Celebrating my birthday in style … and by that I mean, in pajamas. I made Justin PROMISE not to sing ‘Happy Birthday’ to me, so he improvised. Sorry you can’t hear it, but I’m still laughing,” she wrote. “Thank you, you wonderful human, for really listening to me, and for throwing my kinda party. And thank YOU ALL for the birthday wishes. Feeling the love.”

The family of four had reportedly been isolating amid the coronavirus pandemic at their home in Big Sky, Montana, along with Jessica’s mom, Kimberly Biel.

​They enjoyed the wide-open space for months. “Out here social distancing with the fam and a lot of these. I hope you guys are staying safe and healthy,” Justin captioned a snowy photo of the Stealth actress in the mountains on March 25, 2020. “We need to stick together and look out for each other during this crazy time … While there’s a lot of chaos and confusion right now, there’s also a lot of good and so many ways to help.”

July 2020

Life & Style confirmed Justin and Jessica welcomed baby No. 2 — a boy — after the starlet’s top-secret pregnancy.

“They told very few people. This has really brought them closer together again. They’d just learned they were having baby No. 2,” an insider told In Touch about Jessica’s private pregnancy with son Phineas. “It was a very difficult few months for them, but they came out on the other side, and now they have this beautiful little boy.”

September 2021

Nothing screams “date night” like a game of Scrabble. Justin showed off the pair’s night in on Instagram.

May 2022

The couple of the hour stunned on the red carpet at the Candy premiere. 

June 2022

While enjoying some time off in Paris, the lovebirds strolled arm-in-arm through the city.

October 2022

Now, this is a top look of theirs! They matched in black and white ensembles for a sweet red carpet appearance.

February 2023

Jessica shared a rare photo of the loving couple together on a boating trip while celebrating Justin turning 42 years old.

“Happy Birthday to the person who challenges and inspires me every day. The person who keeps me laughing and creating and risking it all. The person who makes the ordinary extraordinary. You know who you are. I love you,” the actress gushed in the caption.

November 2023

Though Jessica put on a brave face to support Justin at the premiere of his new film, Trolls Band Together, she was reportedly wrought with new “trust issues” in their relationship.

An insider told Life & Style exclusively in January 2024 that revelations in Britney Spears‘ memoir, The Woman in Me, released one month prior, had left a bad taste in Jessica’s mouth about her husband. Among Britney’s claims in the tell-all was the bombshell that Justin had reportedly pressured her to get an abortion after she accidentally became pregnant while they were dating during the late 1990s and early 2000s.

January 2024

Rumors began to swirl that Justin and Jessica may be headed for a split, an insider exclusively told Life & Style.

“Though they do love each other, all of the couples therapy they’ve undergone simply isn’t fixing some of their underlying issues,” the source revealed, citing Justin’s 2019 PDA scandal and revelations regarding the “SexyBack” singer in Britney Spears’ memoir as cause for tension in their relationship.

The insider noted that although the couple had survived a split in the past, another “may be for good” as the two now stand at a “crossroads” in their marriage. “Justin and Jessica have two great kids, and they’d love to make it work — it just may be too late.”

January 2024

Despite buzz about possible trouble in paradise, Justin released a new song called “Selfish,” which seemingly referenced his relationship with Jess.

“Every time the phone rings I hope it’s you on the other side,” he sang. “I wanna tell you everything, everything that’s on my mind, and I don’t want any other guys taking my place, girl, I got too much pride.”

He also crooned, “If they know what I know, they would never let you go, so guess what? I ain’t ever letting you go.”