TV presenter Caroline Flack was alleged to have had a series of popular former beaus including Russell Brand, Robbie Williams, TV presenter Steve Jones, Radio 1 DJ Colin Murray and MTV's Alex Zane.
The 29-year-old was purported to be a regular at North London's infamous Hawley Arms pub, known to be the favourite hang out of revellers often high on drugs and alcohol.
And her several dates with Jack, including their bathtime frolics at his Los Angeles home, were suggested to have stemmed from her 'celebrity fascination'.
"She's never been short of celebrity admirers. Jack Osbourne was completely smitten," the News of the World quoted a pal as saying.
"But her friendship with Jack was all about who they were and not because she particularly liked him. However when Jack invited her to come and stay at his home in Los Angeles she had her romp with Jack and another girl in his hot tub.
"Caroline described it as 'nothing more than kisses and boobs'-but makes no secret of the fact that she has experimented sexually with women too.
"She admits she likes to kiss and touch other girls but always insists she'd 'never go below the waist'. She's very friendly with a girl TV presenter and loves to show round photos she has on her phone of them both naked in a bubble bath," the pal added.
Flack was also apparently snapped carrying out a raunchy 'lesbian' dance show with a female friend as the two caressed each other.
She was further reported to have eyed the royal four years ago and "finally wangled her way in!" after dumping drummer boyfriend Dave Healy to be with Harry.
A friend said: "Prince Harry and Caroline are like chalk and cheese but perhaps that's where the attraction lies. He's fascinated by her wild, carefree attitude and rock-chick lifestyle.
"He's not really her type though. She normally goes for cool, grungy Indie musician types. But I've only ever known Caroline to date a celebrity. The main criterion is fame.
"And they don't come much more famous than Harry. If he wasn't a royal I doubt she'd be interested."
The pal added: "It's taken four years to do it but once Caroline targets a man, she'll stop at nothing."