The year-old singer has been enjoying the company of a multi-millionaire businessman 15 years her senior. She made no secret of her affection for Phil Maloof, 36, as they shared a candlelit dinner at a Las Vegas restaurant. Miss Spears and Maloof then adjourned to a club in nearby Mandalay Bay where they danced for most of the night. Now she's dating a man in his mid-thirties. What will she do next? Latest Headlines U. Britney's dating an older man Britney Spears has tried smoking, drinking, bad boys and late nights in her attempts to reinvent herself. Now, it seems, she is trying older men.

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Published: July 24, Britney needs a black dude? A new video has surfaced showing Britney leaving a Ralphs supermarket in Los Angeles with her then boyfriend, Adnan Ghalib, in January You guys are cool.
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A true cast of characters, including Criss Angel. Why he's significant: He's one of Britney's first boyfriends and is one of the most iconic people from her hometown, Kentwood, Louisiana. Reg Jones is a legend.
Britney Spears' mother is set to lift the lid on the troubled singer's life - with revelations that she was drinking at 13 and lost her virginity the following year. Mrs Spears also says her daughter lost her virginity aged 14 to an year-old high school football player soon after she quit the programme. Britney Spears' mother Lynne's new book contains explosive revelations that the star was drinking at 13, sexually active at 14 and took drugs at A source has told how Britney was dating the football star while at school, and how her mother encouraged the relationship because she thought it would make her more popular. The budding singer spent a lot of time at her boyfriend's house and eventually lost her virginity there. Her mother later admitted she regretted allowing her to date an older boy but still allowed her to share her bedroom with new boyfriend, Justin Timberlake.