Still Single Jennifer Love Hewitt
She was engaged to Ross McCall but they called off their wedding in 2008. After her break with McCall she had a two-year relationship with Jamie Kennedy, during which time she famously admitted to having three engagement rings on hold at Tiffany and Co, possibly scaring Kennedy away.
She has had a few other high-profile flings including John Mayer, Alex Beh, Carson Daly and John Cusack. Most recently she was embarrassment after voicing her crush on Adam Levine on Twitter. Levine responded by calling Jennifer aggressive which only added to her shame. Poor girl is chastised just for being honest.