Rachel Bilson Was Once ‘So Obsessed’ And Flirting Madly With A Pop Star But Got Sabotaged By Her Drunken Best Friend

Rachel Bilson’s podcast (she co-hosts Broad Ideas) can go off the rails at times. This cost her a job, unfortunately, after someone involving a production balked at how she made forthright admissions about her sex life. That went down after she fondly recalled Bill Hader’s massive dong and detailed how she only experienced her first orgasm “from, like d*ck” after hitting her late 30s.

This summer, though, she’s kept things out of the headlines but is attracting attention after discussing the Pop Star Who Got Away. As relayed by PEOPLE, Bilson led into the conversation about how she crushed on Justin Timberlake, and how, “In our day, Justin Timberlake was very big, right? Like, the biggest.” She also apparently had a shot in the aughts: “We were all at a party, or something, and he was there, and I was so obsessed with him.” However, her co-host and BFF, Olivia Allen, then detailed how she ruined it for Rachel:

“We were kicking it with him. We were making friends with him. [Bilson] went up to him, obviously, or he came to [Bilson],” Allen chimed in. “I got drunk and embarrassed myself a little because he was trying to flirt with Rachel.”

She then planted herself in between Bilson and Timberlake. She admitted that she kind of sabotaged her friend’s potential moment with the *NSYNC singer, explaining, “I was just drunk and wanted to keep talking to him.”

Olivia apparently, according to Rachel, “squeezed herself” in between the two, and that was that. No one walked away satisfied, although Timberlake apparently had a sense of humor the next time he ran into Olivia: “[H]e was like, ‘What’s up, enemy?'” And the rest was (with JT and Jessica Biel) history.