The downcast singer and his entourage departed Greystone Manor in West Hollywood minutes after his on-off again girlfriend Rihanna, who walked out on her own.
Also partying at the hotspot was his ex-girlfriend Karrueche Tran who arrived on the arms of another man.
Chris Brown appears to have
watery eyes as leaves Greystone Manor in West Hollywood on Monday
morning 10-minutes after Rihanna departed
He pulled his flat cap over his eyes as he was driven out of the club, but it clearly looked like he was attempting to hold back the tears.
Meanwhile Rihanna certainly didn't look like she was crying as she stalked out ten minutes prior to her lover.
Wearing a super-tiny red strapless number, she appeared flawless as ever with her sultry red pout and half-shaved head.
Heading home alone: Rihanna walked out of the club ten minutes prior to Chris Brown
A not so smiley face emblem stuck its tongue out on the left-hand side of her jacket, marking the 23-year old out as the rave girl the world knows her to be.
She finished off her outfit in typical Rihanna style, with layers of gold chains around her neck - including a floral design with the words 'Gran Canaria' on it (from her recent trip there) - a gold watch, bracelet and rings adorning her wrists and fingers.
Her style may be influenced by supermodels of the past, she considers her female family members as role models for her present.
The singer shared an image of herself with her mother and grandmother on Instagram on Sunday with the caption '#rolemodels***'.
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