He's been linked with a bevy of beauties from Hollywood actress Lindsay Lohan to Belfast model Orlaith McAllister.
Now it seems George Best's lothario son Calum has struck up a rather unlikely romance with the teenage daughter of billionaire Chelsea FC owner Roman Abramovich.
According to tabloid reports, 31-year-old Calum has been dating Anna (19) for over a month after forming a friendship several years ago. The pair, who met on the London party circuit, were pictured together soaking up the sun in Sardinia last week.
Dark-haired Anna, who studies business management at Westminster University, is atypical of Best's normal busty, glamorous girlfriends. But the couple are said to have more in common than their fathers’ connections with football.
One source told Grazia magazine: “Don't be fooled by her preppy looks. She can be really crazy and Calum is really attracted to that.
“Calum was over in Sardinia for Sky Sports last week so Anna joined him. It was the first time they'd been out out in public.
“He is really mad about her, but she's understandably keeping her guard up as she knows only too well about his playboy reputation. But there's definite chemistry there.”
It is understood Best is keen to shed his Casanova image and friends say that his 19-year-old girlfriend, reported to be worth a cool $2bn, could be the one to tame him.
The friend said: “Anna is keen to knuckle down with her studies now, and Calum is fed up with his image as a bad-boy party animal, so together they seem to have formed a bond.”
This isn't the first time Anna has been romantically linked with an older man.
At the age of 18 — and while still at school — she shocked fellow pupils by announcing she was engaged to Moscow-born solicitor Nikolai Lazarev (27).
And she hasn't been shy when boasting about her conquests. Three years ago she took to Twitter to post: “Hooked up with a very sexy boy tonight...dropping him off at his...xxx. Had the best night ever!!!”.
She has since deleted her Twitter profile.
Her Russian father is one of the richest people in the world having built up an estimated fortune of £7.8bn with various business interests, including Chelsea.
Best's chequered love life has also been high profile. The model and television presenter, who is returning to Ireland later this year to take part in RTE's Celebrity Bainisteoir — his seventh reality TV show — has been linked with numerous models and actresses including Kate Moss, Patsy Kensit and Elizabeth Jagger.
The conquests of Bestie’s boy
- Orlaith McAllister The Belfast model met Calum Best in the Apartment Bar in March 2005 after taking part in Big Brother. They went on a number of dates together.
- Elizabeth Jagger The model daughter of Mick Jagger was caught on CCTV in a steamy clinch with Best in 2005 outside a London nightclub.
- Lindsay Lohan Best dated Lohan after meeting her in November 2006 in a London nightclub. The pair allegedly split over his womanising.
- Sarah Harding Best dated the Girls Aloud star in 2005/2006. Last year, when it was revealed she had booked into rehab, he said he would always “support and love her”.
- Simona Sofia Best fell for the charms of Italian model Sofia in 2011, even taking part in a Hello! magazine shoot with her. They split over claims he cheated on her.
- Georgia Salpa Best and Salpa went out last year but she dumped him after he was linked to TV host Donna Air.