Justin Timberlake and Jessica Biel Relationship Timeline: Then and Now

In it for the long haul! Justin Timberlake and Jessica Biel’s relationship timeline is full of ups and downs — from a brief split to a PDA scandal. However, they’ve been together for over a decade and proven time and time again that their love is endgame.

The “Sexyback” singer and Limetown actress entered a new chapter with the arrival of their second child. The Total Recall star gave birth to their newborn son after a top-secret pregnancy, Life & Style confirmed on July 20, 2020. The pair welcomed their older son, Silas, in 2015.

“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.”

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’ve been enjoying 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.”

Their baby bliss comes nearly a year after 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.

The Friends With Benefits actor later 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.”

Now, the two seem closer than ever! They even landed roles in the 2022 Hulu series Candy together. Jessica portrayed Candy Montgomery, a real-life woman who killed her best friend in the ‘80s before being acquitted of murder, and Justin played the investigating detective.

Despite the highs and lows, Jessica and Justin seem like one solid couple. Keep scrolling to see their full relationship timeline.

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.”

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.

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.”

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.”

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.”

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.