Terence Kirk badgered the woman to make her “as upset as he was” after she reported him to police over numerous text messages he had sent her.
Chesterfield Magistrates Court heard in August Kirk was warned by officers not to contact the woman - who he had known for four years - anymore.
Prosecutor Andrew Conboy told how after being spoken to by police Kirk sent further messages.
And later he pulled up on the woman’s street and “watched the address for a number of minutes, pipping his horn”.
During a police interview which followed Kirk - who was having problems with his marriage - said he and the victim had “good friendship” and he had supported her with alcoholism.
Mr Conboy said: “He accepted he had been warned not to contact her but said he felt humiliated.”
The prosecutor added that after sending more texts - and thinking the victim’s number had been changed - Kirk took the more drastic step of showing up near her home in his car.
Mr Conboy said Kirk told police: “He had no intention of harming her and he had no intention of ever seeing her again.”
However Kirk’s solicitor Steve Brint, mitigating, told the court that after being warned initially against further contact by police Kirk had received “six phone calls” from the victim between 11pm and 6am” one night.
Mr Brint said the calls were not recorded on the pensioner’s phone but he then responded with text messages.
He said: “Mr Kirk is 82 years old and has never been in trouble before - it was a close friendship, she has her issues and he supported her with those issues.
“He supported her financially and went out for a drink with her when she wanted - to the detriment of his marriage. This is a blip in 82 years.”
Kirk, of Redvers Buller Road, Chesterfield, admitted harassment.
He was handed a one-year conditional discharge, a 12-month restraining order, made to pay £85 court costs and a £22 victim surcharge.