Watch: Britney Spears Turns Down Former Duet Partner on X Factor

It was a tense and rather awkward moment on the X Factor stage when Britney Spears had to send home one of her former collaborators, Don Philip. Video of his audition in full is above.

Shot over the summer and hinted at in tabloid reports at the time, the moment was indeed drama-filled. Don Philip recorded a duet with Britney almost a decade ago, and he actually thought he’d make it through to the next stage on X Factor.

This was his last chance of forging a career in music, as he says in the introduction video. As bad luck would have it, none of the four judges thought he had a good singing voice.

Not only did Don cry when he first got on stage, when he saw Britney, but he also burst into tears when he was rejected.

From what he told the crew, it didn’t pain him so much that he didn’t make the cut as it did having to put Britney in a position in which she had to tell him he was no good.

Awkward moment, indeed.