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Robber Malcolm Shipley targeted a woman working in a Rochester charity shop and then stole £1,200 in donations.
The sweet-talking 44-year-old villain convinced lovelorn Melissa Lowson he had fallen for her.
But then he stole the safe containing £600 from the Sue Ryder charity shop in Rochester and ordered her to make a burglary claim.
Weeks later, Shipley wormed his way back into her life, only to rob her of another £600 at knifepoint.
On the day he was due to face trial at Maidstone Crown Court, the judge gave him permission to talk another woman - and afterwards he changed his pleas for the charges of robbery and theft to guilty.
Prosecutor Mary Jacobson said Shipley had befriended the mum-of-four in 2016 while she was working at the shop and “then deliberately manipulated things to take advantage”.
On September 25 that year, the devious Shipley suggested taking the charity money and faking a break-in.
The prosecutor said Ms Lowson “put up considerable objection” telling him it was her job but he began shouting at her and made threats.
The thief used gloves and pliers which had been donated to the shop to steal the safe.
Ms Jacobson said Shipley then ordered her to report the theft “which she did through fear”.
Afterwards, Ms Lowson didn’t hear from her lover for two weeks but then he “rekindled the relationship by speaking of them marrying”.
“This was a ploy to convince her he was in love with her because he soon returned to being violent and controlling.”
“Again she objected but he went into the back office and took a knife and placed it to her throat.” - Ms Jacobson
Two months later they went into the shop and he said they should pretend there was a robbery.
“Again she objected but he went into the back office and took a knife and placed it to her throat.”
Ms Lowson reported the robbery but she was too scared to say it was Shipley.
In May 2017 he was arrested but then went on the run, staying in caravans and tents until he was caught again.
In an impact statement, Ms Lowson, who lost her job over the thefts, said the incidents had a profound effect on her life - going from a “bubbly girl” to someone who almost gave up on life.
Shipley told the judge he had now “given up on crime and given up on the police”.
He added: “I just want to say thank you for giving me the opportunity to speak with my partner. I have turned my life around.”
Shipley, who was jailed for four years, turned to his lover sitting in the public gallery and said: “I love you.”
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