That's One Toothless Smile! Robin Thicke Leaves Dentist Office Missing Some Teeth

Robin Thicke, what is up with your smile? The R&B crooner left a dentist’s office and it looked like he only had one tooth!

Robin quickly went from smoothest to toothless as he revealed a missing tooth (or two or three) while in Encino, Ca. The lady-loving "Blurred Lines" singer must have been caught in the middle of dental surgery as he showed off the unsightly gaping hole where his front tooth used to be.

Still, he looked pretty stylish in his black on black outfit. Unfortunately, his much younger girlfriend April Love wasn’t around to make him feel better about his grin.

But clearly, Robin was not that committed to oral hygiene as he puffed on a cigarette while waiting to fix his million-dollar smile. Put it down, Robin!

Meanwhile, in other news, Robin apparently feels just as terribly about his last album, Paula, as we all do.

After his performance of “Forever Love” at the 2014 BET Awards, which was in honor of his ex-wife Paula Patton, he realized it was more embarrassing than anything. Robin told Billboard, “My best friend of 20 years, Craig Crawford, said, ‘I saw your BET performance.’ And I said: ‘Oh yeah! What did you think?’ You know — excited. And he goes: ‘I gotta be honest with you, buddy. You’re kind of playing yourself. You look like a sucker.’ And it hit me that I’d lost my perspective. What I thought was romantic was just embarrassing.” Ouch.