49.Alyssa Milano and Justin Timberlake

The singer Justin Timberlake’s dating life was a media favorite before he met his wife. He has dated several high-profile personalities such as Cameron Diaz, Fergie, and Britney Spears. Alyssa Milano came forward and talked about their short time together in 2002. The actress is known for her acting credits as Phoebe Halliwell in Charmed and as Jennifer Mancini in Melrose Place.

According to her, she and Timberlake dated for a few months. Their relationship was so short-lived that it did not even reach the media’s attention. She later admitted that after Timberlake’s romance with Spears, she hooked up with him in 2002. Aware that the Cry Me a River singer was not over his ex, she decided to call it quits. Now, Timberlake has been married to Jessica Biel since 2012, while Milano has been with her husband David Bugliari since 2009.