“Predatory” thief Simon Cohen dated a Jewish woman to gain access to her home in order to plan a future break-in.
His crimes have left his victim's trust in others shattered, a court was told.
Because he was creeping into her house when she wasn't there, she even thought she was "going mad" because she couldn't explain how she kept losing things, including a cherished Star of David.
Thirty-two year old Cohen was jailed for four years when he appeared for sentence at St Albans Crown Court.
It was in April last year that the woman's home in Borehamwood was broken into and an iPad and money was stolen.
The victim, who was not named, reported it to the police who arrested Cohen, of Colindale, north London, tracing him through the Find My iPad app on the stolen device.
Images found on his phone made officers realise it had not just been an opportunistic break in.
There were close-up pictures of the woman's house keys on it as well pictures of banking documents and the outside of the property.
Police discovered that Cohen had met the woman through an internet dating agency in late 2013.
She had ended up inviting him to her home in the December and he had stayed the night.
Miles Trigg, prosecuting, said "She realised there had been times when he left the bed to go and have a smoke, when what he was doing was having a search and taking images of banking documents and information to allow him to get back into her home."
There were close-up images of her house keys on the phone and it was discovered Cohen had been researching on the internet how to make keys from images.
The woman told police how, 11 days before her iPad had been stolen, she had gone to meet another man she had been in contact with on the internet dating agency, only for him not to show up.
When she returned to her home, a necklace was missing, along with more than £550 and 300 dollars.
Mr Trigg said it transpired that Cohen using a false identity and had lured the woman out of her home so that he could break in.
Judge Stephen Warner, hearing the case, was told that Cohen had used the details of another man to create a fake profile after acquiring his banking details and a driving licence.
The court heard how Cohen had met a second woman via the online dating agency and had visited her at her home.
While there, he had taken images of her banking documents which he intended to use for later frauds.
Mr Trigg said "She now feels vulnerable, stupid and violated."
Cohen pleaded guilty to two offences of burglary and two offences of possessing articles for use in fraud.
In court he was described as a petty criminal with a long standing addiction to class A drugs.
Passing sentence, Judge Warner told Cohen that what he had done had been a serious breach of trust.
He said they were "mean and cynical" offences and he said a report by the probation service into his wrong doing had rightly described him as "predatory and manipulative."
He jailed him for four years.
