Father-of-three Stuart Innes, 47, has never been able to move on from the break-up of his marriage six years ago and the loss of the £1 million fortune he and his wife built up in business together.
Innes, from Aberdeen, claims ex-wife Rachel made him sign away his share of their business and £700,000 home in Cheltenham on the promise they might get back together.
At Gloucester crown court Innes, an engineer who ran a care home with his wife, admitted three breaches of a restraining order which prevents him contacting her or her solicitor.
Prosecutor Lisa Hennessy said: "He is no stranger to this court. He has breached the same restraining order 17 times. The longest sentence he has so far served is 18 months."
That sentence was imposed in 2011 after Innes doused himself in petrol in his flat and threatened to set himself alight – leading to the evacuation of the building and a police siege.
The judge, Recorder Michael de Navarro, QC, said "There are three problems – his failure to recognise that the marriage is over; his feeling that he has been done down financially; and the issue of access to his children.
"Frankly, the longer he goes on failing to recognise the first, and failing to resolve the second by sensible means, the more difficulty there is going to be in resolving the third.
"At some point he is going to have to wake up and stop making an absolutely confounded nuisance of himself."
The latest breaches of the restraining order related to him sending 11 letters to his ex-wife's solicitors.
Innes, who represented himself, told the judge: "I hurt her and she divorced me. She said I had to prove how much I loved her by signing over everything to her and then maybe one day she would have me back. I thought it was a lot to ask because she was moving in with another man and I did it against legal advice."
He begged the judge not to jail him again and said that if he was free he would return to his native Aberdeen.
The judge said: "This is a very sad case. You are obviously intelligent and highly articulate." But he said that given the multiple breaches in the past he had to impose a custodial sentence.