In reality, however, the 52-year-old was a serial fraudster who cheated his victims out of half a million pounds.
One lent him £10,000 after he claimed to need money for a vital operation to cure his fictional Parkinson's disease.
Others gave him cash for invented business dealings as he posed variously as an architect, property developer, fighter pilot and Vietnam War veteran. One woman ended up losing her house.
He spent the money on Mercedes cars, Harley Davidson motorbikes and Rolex watches.
Justice finally caught up with Checkley, described in court as 'a man with a golden tongue' yesterday when he was jailed for six years and ten months.
Police believe he managed to swindle more than 30 victims out of at least £500,000 but the Crown settled on 13 specimen charges of fraud totalling £163,000.
Some of his victims - who had lost between £2,000 and £50,000 each - were in court as he was jailed.
Judge Mark Horton, sentencing at Bristol Crown Court, said: 'Over 20 years you targeted and preyed upon vulnerable and often lonely women.' (call him what he is: a SOCIOPATH!)
Grenada-born Checkley, who emigrated to America with his family when he was three before they moved to London when he was 11, was warned by the judge he faced deportation upon release.
Don Tait, prosecuting, had earlier said: 'It is the Crown's case that this defendant was a consummate fraudster - a man with a golden tongue.'
Checkley met women on the Dating Direct and Match Affinity websites before convincing them he was a businessman with the chance to make high-stakes investments.
He even proposed marriage in an effort to get women - some of whom he forced to re-mortgage their homes - to give him money.
Among his victims was Sharon Shearer, who gave him £30,000. She ended up losing her house.
Another, Linda Miller, handed over £10,000 after Checkley told her he had Parkinson's and needed the cash for an operation after meeting 'fellow sufferer' Michael J Fox.
Deborah Bacaglieri passed over power of attorney and lost £27,000.
Susan Baio, who Checkley defrauded out of £3,155, said after the hearing: 'I'm delighted with the verdict. Hopefully he will never come near me or my family again.'
Checkley's daughter Amy said she was 'disgusted' with her father, adding: 'I hope he's deported.'
* In 2002 Checkley was jailed for GBH and false imprisonment after luring Mark Levy, a presenter on Channel 4's Big Breakfast, to a fake Rolex deal where he was murdered. Two other men convicted of the attack were later cleared.