A lonely Post Office director defrauded almost £350,000 from the company over 11 years "to buy love and affection", a court heard.
Paul Swanton, 52, used the cash to clear his overdraft, visit nightclubs and fund relationships.
He confessed he was "driven by desperation" and a spending addiction.
Swanton, of Furzton, Milton Keynes, admitted 16 counts of fraud by abuse of position and was jailed for a year and eight months at Southwark Crown Court.
He had risen through the ranks from a counter clerk in 1986 to director sitting just below board level, earning £86,000 annually.
Swanton's "catastrophic fall from grace" - as described by the judge - began in 2007 when he began ordering gift cards and postal orders for himself, rather than for legitimate business.
'Lonely personal circumstances'
A fraud investigation team uncovered his scheme when it looked into suspicious deposits of postal orders, the court heard.
In a resignation letter in March last year, he said his public face was one that worked hard to make the Post Office a success but there was "a private one driven by desperation" and "a need to buy love and affection".
Judge Michael Grieve QC told Swanton: "You have lost your employment, livelihood, any prospect of having anything other than a lowly paid status and employment.
"You accept, and it is not an excuse, you were in the grip of something akin to an addiction arising out of your personality and lonely personal circumstances."
Toby Long, defending Swanton, said he was "in a wretched state... caused entirely by his own actions".
"He did not have a partner and he would say that he had to spend money not to be lonely," he added. "He felt that if he spent, they would remain his friends."
Swanton's fraud cost the Post Office a total of £348,819 and he was ordered to pay £379,613 in compensation.