Serial ‘Internet Romeo’ fraudster who conned 10 ‘lonely hearts’ he met on the Plenty of Fish dating app out of £111K which he then splurged on fleet of Mercedes cars and Harley Davidson motorbikes is jailed for 11 years

A serial ‘internet Romeo’ who has spent more than a decade conning vulnerable ‘lonely hearts’ is back behind bars after duping 10 women out of £111,000.

‘Fantasist’ David Checkley, 65, spun a ‘web of lies’ after meeting his victims on the dating app Plenty of Fish, convincing them he was a ‘billionaire’ or Vietnam War veteran. 

The career conman – who who was jailed for five years in 2002 after luring Channel 4 presenter Mark Levy into a fake Rolex deal in which he was murdered – splurged his ill-gotten gains on a fleet of Mercedes cars and Harley Davidson motorbikes. 

The lying lothario’s scheme was similar to the previous con the love cheat ran in 2010, which saw him being jailed for six years after duping dates out of £500,000 by pretending he needed money for an expensive new cure for his ‘terminal illness’. 

‘Remorseless’ Checkley committed his latest spree against women in their 50s, 60s and 70s between February 2017 and February 2021, using Plenty of Fish to hunt down his victims, who had recently broken up. 

‘Fantasist’ David Checkley, 65, spun a ‘web of lies’ after meeting his victims on the dating app Plenty of Fish

The crook had used victim’s cash to buy two new Harley Davidson motorbikes worth approximately £40,000

The ‘ruthless’ 65-year-old crook fabricated stories to trick victims ‘into believing he was an intelligent, knowledgeable and powerful man’, the Metropolitan Police said, before encouraging them to send him money. 

His stories included him being a US fighter pilot, a Vietnam War veteran, a successful architect. He also dreamed up a series of previous fake wives, including the daughter of telecommunications boss, an American billionaire and a Chinese heiress.

Checkley targeted women who were recently out of relationships, lonely and in some cases desperate for a serious relationship. 

The crook was jailed for almost seven years back in 2010 for a similar crime 

He would ask to borrow money, claiming his house was falling down, or that he had the opportunity to buy a Rolex at a knock-down price, before splurging cash on cars and motorbikes. 

But some became suspicious and went to the police after discovering their relationship was entirely faked.

One of Checkley’s latest victims, Lise Johansen lost everything was made homeless by his conniving ways. He even stole an eternity ring that previously belonged to her mother as she wrapped Christmas presents.

Checkley was convicted of 19 counts of fraud and one count of theft, with the total deception coming to about £111,000, London’s Old Bailey heard. 

Passing sentence, Judge Recorder Jonathan Laidlaw, KC, said: ‘I am in no doubt you are a ruthless and professional conman, you identified women who you recognised you could impress.

‘These women, some of whom were lonely were for you an easy piece of manipulation

‘It was offending on a prolific scale… there is not a single element of remorse.’

Prosecuting, Rekha Kodikara said the con was a ‘repeat performance’ of Checkley’s previous fraud.

Some of the victim’s money was also spent on buying this Mini Cooper 

‘These offences were well planned, sophisticated offences,’ the prosecutor added. ‘He used a false name and with that name, he duped the victims.

‘It is clear from the evidence that the defendant chose his victims knowing their vulnerabilities.

‘Some of the victims had unhappy relationships, some were lonely, some were ill and they were looking for a long-term relationship.

READ MORE: Internet Romeo conned dozens of women out of £500,000 pretending to be terminally ill

‘Unfortunately for them, that is not what they received.’

The court heard how Checkley would tell his victims that he was required to travel for work, which is how he managed to keep up so many relationships.

The longest of his relationships lasted four and a half years. He was arrested after returning from a holiday to Ibiza in July 2021. 

When police a searched the Harrow home of one of his victims, officers discovered invoices relating to the purchase of expensive jewellery, a brochure for a large mansion in Hertfordshire and a receipt in a woman’s name for a £7,250 Rolex watch purchased in 2018. 

A search of the garage, uncovered two new Harley Davidson motorbikes worth approximately £40,000 which had been purchased using Checkley’s account. A Mini, and three Mercedes all linked to Checkley were also found parked near to the address. 

Checkley spent cash on this Mercedes after conning his victims 

Passing sentencing, the judge, Mr Recorder Jonathan Laidlaw, KC, said: ‘You have no understanding at all of the damage you have done to another 10 women.’

Some of Checkley’s victims attended court and they applauded as his sentence was announced.

Judge Laidlaw addressed the victims present saying: ‘I am quite certain no sentence is going to do justice, but I hope it will become clear that these are criminal offences, they are not your fault on any of these convictions.’

Speaking after the sentencing, Detective Superintendent John Roch, from the Met’s Economic Crime Team, praised the victims for their ‘courage’ in coming forward. He said: ‘There is no doubt that Checkley is a prolific and systematic fraudster who spun a web of lies to his victims. 

‘He abused the honest intentions of his victims in the most callous way. He is a fantasist who claimed to lead an enviable lifestyle but in reality, he is a criminal who deceived innocent people for his own financial gain.

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