Justin Timberlake’s Disastrous Attempt at Flirting With How I Met Your Mother Actress Backfired Long Before Cheating on Jessica Biel Rumor

It is common knowledge that celebrities date other celebrities. And Justin Timberlake’s love story(ies) are no exception!

Justin Timberlake’s Disastrous Attempt at Flirting With How I Met Your Mother Actress Backfired Long Before Cheating on Jessica Biel Rumor


  • Needless to say, Justin Timberlake has faced more challenges in his love life than in his work.
  • His marriage to Jessica Biel has been solid, despite an awkward hand-holding scandal and his disastrous flirtation with Rachel Bilson.
  • Despite the challenges, Timberlake and Biel’s marriage has been strong, and they are proud parents of two children.
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Well, the world of celebrity romance – chock-full of glitter, glamour, and sometimes disaster. Even Hollywood’s most desirable stars, such as Justin Timberlake, can stumble when it comes to romantic matters. Having said that, he has been through many storms in the spotlight. Even in a world where celebrity couples break up faster than you can say, “maybe let’s not get married”, his marriage to Jessica Biel has always been pretty damn solid.


With the exception of a brief breakup and an awkward hand-holding scandal, these two have been together for more than ten years, having first met in 2007. Put another way, nine years longer than the average length of time for a celebrity relationship. Yes, a lot has happened in that time, such as the published memoir by Britney Spears or his disastrous attempt at flirting with How I Met Your Mother actress Rachel Bilson. 

Justin Timberlake in 2021's Palmer
Justin Timberlake in 2021’s Palmer

Also read: “You can’t flirt like you did last time”: After Marrying Justin Timberlake, Jessica Biel Had One of the Most Memorable Bits With Conan O’Brien


An ‘Embarrassing’ Drunken Encounter Rachel Bilson Had with a Flirty Justin Timberlake

You probably already know that famous people date other famous people. Usually, we hear about people who have achieved great success, but sometimes they have let others go before them. For example, though they do not seem to be in the same social circles, Rachel Bilson and  Justin Timberlake have crossed paths before.

Bilson talked about their interaction. Things seemed to be going okay enough after a friend and some alcohol got involved, but before she knew it, everything had cooled off. The actress told the story of an “embarrassing” drunken encounter she had at a party back in the early 2000s with Timberlake on a previous episode of her podcast, Broad Ideas with Rachel Bilson & Olivia Allen (via PEOPLE):

Rachel Bilson
Rachel Bilson in How I Met Your Mother

She struck up a conversation with her co-host, Olivia Allen:


“In our day, Justin Timberlake was very big, right? Like, the biggest. Sorry, no disrespect — he’s still very big. We were all at a party, or something, and he was there, and I was so obsessed with him.”

Then Bilson faltered, saying she was unable to relate the tale. Her co-host, though, was not going to let her off the hook just yet. However, right as Timberlake and Bilson were getting along, Allen—who was, to be honest, inebriated at the time—sat down between them. Allen uttered:

“I was just drunk and wanted to keep talking to him.”

Allen tried to get Timberlake’s attention by squeezing herself in between them after Bilson informed her that there was “no room” for her. That fateful evening, however, saw nothing happen between Timberlake and Bilson. 

Jessica Biel with Justin Timberlake (@jessicabiel | IG)
Jessica Biel with Justin Timberlake (@jessicabiel | IG)

Regretfully, it was not intended to be. In 2012, Timberlake tied the knot with Jessica Biel in Italy. However, their marriage has also been plagued by rumors of cheating.


As for Bilson, she has a daughter with her ex-partner, Hayden Christensen, whom she got to know while working on the 2008 flick Jumper

Also read: “I don’t know how to play this part”: Kate Winslet Was Unsure About 1 Movie With Justin Timberlake That She Absolutely Hated Playing

Has Justin Timberlake Been Unfaithful To Jessica Biel? 

The internet was set ablaze when rumors surrounding Justin Timberlake’s alleged infidelity towards his wife, Jessica Biel, started to circulate. The power couple, famous for their seemingly rock-solid marriage, unexpectedly found themselves caught up in a whirlwind of speculation and accusations.


When Timberlake went out with friends to a bar in New Orleans in 2019 (via The Sun), he was pictured holding hands with actress Alisha Wainwright, with whom he was filming the drama film Palmer. Naturally, this gave rise to a lot of rumors that he was being dishonest with Biel. 

Sources claimed that the actor, 42, appeared to have drunk a lot of alcohol and was unsteady on his feet. Even so, observers were taken aback when they saw him clasping Wainwright’s hand and running the risk of upsetting Biel, his almost twelve-year-old wife and mother of their sons.

Also read: Jessica Biel-Justin Timberlake Prenup: Jessica Biel’s Reported $500,000 Worth Love Contract Will Leave You Speechless

Jessica Biel with Justin Timberlake (@jessicabiel | IG)
Jessica Biel with Justin Timberlake (@jessicabiel | IG)

Meanwhile, Us Weekly reported that he had cheated on Biel, his current wife, even when they were dating. In October 2010, an outlet was exclusively informed by a source that Timberlake had an affair with Olivia Munn that lasted three days. At the time, the former’s representative flatly refuted the accusations, and Munn’s representative remained silent.

While the tabloids might relish a juicy story of betrayal, it’s important to handle such rumors with caution and empathy. Thus, let’s respect the boundaries of their personal lives and take into account the lessons we can draw from their journey. Ultimately, it is their love story, rather than the scandal, that deserves our respect and admiration. 


Written by Siddhika Prajapati

Articles Published: 1740

Between everyday normalities and supernatural abnormalities, Siddhika Prajapati finds the story in everything. Literature Honors Graduate and Post-Graduated in Journalism (from Delhi University), her undying need to deduce the extraordinary out of simplicity makes her a vibrant storyteller.

Serving as a Senior Entertainment Writer at Fandom Wire and having written over 1700 pieces, Siddhika has also worked with multiple clients and projects over the years, including Indian Express, India Today, and Outlook Group.

Who knows, maybe your next favorite persona on the screen will be crafted by her.