19. Olivia Wilde
In the Spring of 2011, actress Olivia Wilde seemed to be all over Justin Timberlake’s radar. The two were seen hanging out and partying in Los Angeles like they were wild and free. Justin had recently split from Jessica Biel (but don’t worry, they ended up getting married!) and Olivia was recently divorced (she was previously married to Tao Ruspoli.) Justin and Olivia were co-stars at the time in the film Now, and the relationship sparked headlines among gossip magazines. The romance lasted for a hot second, but the two celebs have managed to do quite well for themselves since then.
18. Olivia Munn
Back in the fall of 2010, Justin was reportedly spending a lot of time with Olivia Munn, even though he was in a serious boyfriend-girlfriend relationship with Jessica Biel. So, how did Justin and Olivia meet up? It turns out that Olivia interviewed Justin to get some more details on the movie he was filming,The Social Network. After the interview, she apparently wasn’t done, because Olivia was driven to a hotel by a private driver with Justin in tow! It can be easy to see how speculations of Justin’s fidelity were flying rampant at this time. Luckily, things cooled off, Justin married Jessica, and all is well.
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