For a girl who only last December was visiting Alcoholics Anonymous, picking the party-loving son of a womanizing alcoholic as her latest beau is probably not the most sensible of choices.
Nevertheless, Lindsay Lohan has apparently come to the decision that former model Calum Best is exactly what she needs.
Just days after People magazine reported that the two "shared a very discreet kiss" in a New York nightclub, photographs showing the pair unabashedly frolicking in the Bahamas last weekend hit the gossip magazines. With discretion seemingly out of vogue and the relationship out in the open, the key question is whether Best is the best choice for Lohan.
"Lindsay's track record with relationships is not good," said Michael Levine, founder of LCO-PR.
Still only 20, actress-singer Lohan has already racked up her share of famous exes. Wilmer Valderrama, Jared Leto, Brandon Davis and even Bruce Willis have all been linked with the starlet, and the list goes on.
Having risen to prominence through the 2004 hit film "Mean Girls," Lohan has since become better known as a socialite than an actress committed to her trade.
"These young ladies are known as party poodles rather than actresses," Levine told ABC News. "Lohan needs to focus much less on her personal life and much more on her professional life."
One thing that Lohan and Calum certainly share is they both have a father who endured no small share of bad press.
Lohan's dad is best known for spending his daughter's teen years in prison for fraud and then returning to prison in 2005 after he was jailed for driving while impaired and for attempted assault. Her parents divorce became final later that year.
Calum Best's father, George Best, is known all across Europe as one of the finest soccer players to ever play the game, after starring for Manchester United in the 1960s and '70s. For the British, he was like Michael Jordan in cleats. With long hair and good looks, George Best was labeled "the fifth Beatle" by a press that had never seen a sports star mobbed by teenage girls in this way before.
But George Best was also a flawed genius. He was arrested in 1984 for drunken driving, and his postcareer attempts to reclaim former glories, including playing soccer in the United States, were overshadowed by tales of drunken debauchery. In 2005, George Best died from multiple organ failure as a result of years of sustained alcohol abuse.
So does this unenviable family history mean that Lohan and Calum Best are doomed?
"In psychological terms, common history can be a very bonding thing, as two people can explore their recovery and desire to get through the world in a more sane way," said Levine. "Similar backgrounds can be supportive, but whether the media choose to play up this as a plotline to their romance is not yet clear."
With this parental commonality being both a potential asset and a potential problem, a key factor will be whether the kids can overcome their own failings.
Unlike Lindsay Lohan, 26-year-old Calum Best owes much of his fame to his father. The British tabloid gossip pages have detailed his dating of a multitude of fellow C-list celebs, the most notable of which are actresses Patsy Kensit and Elizabeth Jagger, the model-actress daughter of Rolling Stones lead singer Mick Jagger.