It could simply have been the late hour, but Chris Brown looked distinctly watery eyed as he left a Hollywood club early on Monday morning.

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.

Girlfriend trouble? Chris Brown appears to have watery eyes as leaves Greystone Manor in West Hollywood on Monday morning 10-minutes after Rihanna departed

Late night: The singer was accompanied by his entourage

It can’t have been an easy encounter for Brown, who at one point was reported to be dating both women.

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

Army girl: Rihanna covers up in a camouflage jacket with studded collars

Adding some grunge style to her look, the Diamonds singer wore a green camouflage jacket over her shoulders that featured gold studs on the collar.

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.

Stirring things up? Brown’s ex Karrueche Tran was also at the club

 

Moving on: Tran arrived on the arm of a new man

The Barbadian icon had styled her wavy caramel locks into a side parting and with her left side shaved, she showed both a masculine and feminine side to her personality.

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***’.

Golden: The singer styled her caramel weave into flowing waves to one side

Two-faced: Womanly on the right, shaved on the left, Rihanna’s look had an androgynous element

In other news, it has just been confirmed that Rihanna will join Bruno Mars and Sting in a group performance at this year’s Grammy Awards ceremony, after singing Princess of China with Coldplay at the 2012 event.

The announcement was tweeted from the official awards Twitter account, which said: ‘In case you missed, @BrunoMars @Rihanna + Sting (@OfficialSting) will be performing together at the 55th #GRAMMYs next Sunday’.

Top coat: The Diamonds star had worn a black jacket over her camouflage shirt upon her arrival at Greystone Manor

The Grammys take place on Sunday 10 February in Los Angeles and LL Cool J is returning as host.

Which songs from each artist has yet to be confirmed, but they will join Ed Sheeran, Alicia Keys and Frank Ocean in performing.

Frank Ocean has recently said he will not be pressing charges against Chris Brown after they were involved in a brawl outside a recording studio in LA last week.

According to reports the clas between both parties’ entourages begun over a parking space.

Triple threat: Rihanna, Bruno Mars and Sting will perform together at this year’s Grammy Awards ceremony