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Rachel Bilson details ‘embarrassing’ flirting attempt with Justin Timberlake

Rachel Bilson once tried shooting her shot with Justin Timberlake at a party in the early 2000s — but was thwarted by her friend and current podcast co-host Olivia Allen.

“In our day, [Timberlake] was very big, right? Like, the biggest. Sorry, no disrespect—he’s still very big,” the “O.C.” actress, 42, said on Monday’s episode of her and Allen’s “Broad Ideas” podcast, according to People.

“We were all at a party, or something, and he was there, and I was so obsessed with him.”

Allen recalled the two women “kicking it” and “making friends” with Timberlake that night.

“[Bilson] went up to him, obviously, or he came to [Bilson],” Allen said. “I got drunk and embarrassed myself a little because he was trying to flirt with Rachel.”

That’s when the inebriated Allen decided to plop down between Timberlake and Bilson just as they were hitting it off.

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

Bilson joked that there was “no room,” yet Allen “squeezed herself” in and “battled” against Bilson to try and win the “Cry Me a River” singer’s attention.

While Bilson’s flirtatious attempts didn’t pan out, Timberlake didn’t hold Allen’s “embarrassing” drunken behavior against her.

“The next time I saw him, he was like, ‘What’s up, enemy?'” Allen laughed.

The *NSYNC alum, 42, went on to marry Jessica Biel in 2012. The couple shares two kids: Silas, 8, and Phineas, 2.

Meanwhile, the “Hart of Dixie” star revealed in August that she has a new boyfriend who brings her coffee in the morning.

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While she didn’t divulge any details about the mystery man’s identity, Bilson sparked dating rumors with artist Zac LaRoc after they were spotted showing PDA on a beach in May 2022.

Bilson had previously dated Bill Hader for nearly seven months before splitting in July 2020. Following their breakup, Bilson admitted that she missed the “Barry” star’s “big d–k.”

She also opened up about her dating patterns during an August episode of “Call Her Daddy,” explaining that she’s “dated quite a few actors.”

“I do think that some of them, not all, have very self-involved tenancies,” Bilson said. “I think that just kind of comes along with the territory a lot of the time. I’m not saying all of them that I’ve dated have them, but it is a theme. And I don’t like it.”

Bilson shares daughter Briar, 8, with ex-partner Hayden Christensen, whom she split from in 2017 after dating on and off for 10 years.

And while the “Star Wars” actor also has a career in Hollywood, Bilson noted that he doesn’t have any narcissistic qualities like other actors she’s been with.

“I will say with respect for my daughter’s father, he is not like that,” Bilson said.