Breakup, Rough Birth & Another Gal! Justin & Jessica's Relationship Timeline Exposed
See what Timberlake and his wife Biel endured before he was caught with costar.
Oct. 15 2020, Updated 3:14 p.m. ET
Justin Timberlake's sometimes troubled relationship with wife Jessica Biel took another hit this weekend as new photos and video obtained by The Sun showed the singer getting cozy with co-star Alisha Wainwright during a boozy night out!
As RadarOnline.com reported, Timberlake and Wainwright, who are filming an upcoming movie titled Palmer in New Orleans, took a break from acting with a midnight trip to a bar where they enjoyed some drinks on a balcony.
Timberlake, 38, appeared to be inebriated as he was stumbling and sipping on drinks, but even worse, sexy Wainwright, 30, was spotted stroking the singer’s knee, before he grabbed her hand.
As they held hands, a source told The Sun, “They were smiling and laughing.”
The insider also said of the shocking scene, “At one stage he grabbed her hand and rested it on his knee. She then gently started stroking his leg. Then he clutched her hand with both of his and was playing with her hands.”
Before this sighting, Timberlake and the actress, who play lovers in their new film, hung out with a small group at The Absinthe House on Bourbon Street.
But they reportedly joined the group only after spending 40 minutes alone on the balcony.
Timberlake’s rep told PEOPLE about him and Wainwright, “There is no validity to this speculation. They are currently working on a project together. Members of the cast and crew were all together.”
However, Timberlake's behavior raised eyebrows, especially because he just celebrated his seven-year wedding anniversary with Biel.
The "SexyBack" singer and former 7th Heaven star, 37, have long had a tumultuous relationship.
It started in 2007 when they were first dating and Timberlake admitted it wasn't exclusive.
Although he wasn't married to Biel then, while speaking about failed marriages, Timberlake told Vanity Fair in 2011, “I said that I think the mistake is that people commit to who that person is right then and not the person they’re going to become. That’s the art of staying together, is changing together.”
But Timberlake and Biel eventually reconciled, married, and had a son, Silas.
Scroll through RadarOnline.com's gallery for more on their relationship agony in the wake of the singer being caught with co-star Wainwright.
Sparks Flew
Biel said she "technically met" Timberlake and they first spoke when she attended a birthday party in 2007 he was throwing for one of his friends. Timberlake later asked his friend to ask Biel if he could call her, got her number, and called and asked Biel out on a date.
Playing Hard To Get?
"I had to be pretty persistent in order to get her to say yes," Timberlake later about asking Biel out for the first time. "But I have a fair amount of tenacity and if I want something I stick to it. And in the end, she agreed."
Big Reveal
In May 2007, Timberlake and Biel went public with their relationship, as she joined him on UK leg of his concert tour and photographers captured them together.
Rough Dating Period
When the former boy bander first started romancing Biel, Timberlake admitted he was also still dating "other people."
Two Can Play
But Biel was also playing the field at that time! Timberlake noted, “We were both still seeing other people, keeping ourselves safe from getting hurt, from really putting ourselves out there.”
Love Expressed
In a September 2007 interview, without saying Biel's name, Timberlake said that he was dating someone who "smells lovely" and added that he got "pretty romantic around her."
Too Much PDA?
In 2009, Timberlake decided to make the crowd go wild by straddling Biel at a Lakers game as the "Kiss Cam" came their way. "I mounted my girlfriend in front of 18,000 people," he boasted. Biel just laughed.
Mother Approves
In 2010, Timberlake's mom Lynn Harless praised Biel, saying "She's so down-to-earth and her family is great."
The End For Now
In March 2011, Timberlake and Biel broke up after four years of dating. The stars' reps said in a statement that it was a mutual decision and that "the two remain friends and continue to hold the highest level of love and respect for each other."
Good Memories
Timberlake still had fond feelings for Biel even after they split. In June 2011, he said his ex had been the most significant person in his life.
Back Together
The two started hanging out again in July 2011, going out for tacos and riding bikes.
Popping The Question
In Dec. 2011, Timberlake proposed to Biel in Montana. He has said, "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." She said yes!
Wedding Bells
Timberlake and Biel get married in October 2012 in an intimate ceremony in Italy. The actress went non-traditional, wearing a pink dress, and Timberlake performed a song he'd written for the nuptials.
Baby Makes Three
In April 2015, Timberlake and Biel welcomed their son, Silas.
Blip After Baby
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The couple sought counseling after the actress gave birth after a joke about her being a soccer mom. “A friend of the couple suggested marriage therapy before things got worse,” an insider revealed to RadarOnline.com at the time. Biel “had issues about not feeling "hot" anymore since having their son,” claimed the pal. “It took her ages to get Justin to settle down … the jokes do not sit well with Jess.”
Telling All
In a book by a Hollywood nanny, Connie Simpson, Biel exposed her birth agony. She revealed how much she and her husband struggled after the birth of their baby boy. After undergoing an emergency C-section to deliver Silas, Biel said in the book, “We arrived home exhausted, disillusioned, and totally in shock."
Causing Controversy
Biel got slammed for fighting against child vaccination this year. There was no word on what Timberlake thought about it.
Scary Fun?
In October 2019, Timberlake and Biel and their boy were spotted looking happy together in their Halloween costumes.
Oh, No
But Timberlake was seen at a bar with his movie actress co-star Alisha Wainwright. Will his marriage to Biel be in trouble?
