A smitten Romeo blew any chance he had of wooing the object of his affections by knocking her teeth out.
Paul Garnett punched Ramshill Hotel landlady Gillian Waterworth - and she now needs extensive dentistry work to repair the damage.
The 55-year-old now faces jail for the brutal Boxing Day assault.
Garnett had hoped that his pursuit of the boss of his local would end up in courtship rather than in court.
Scarborough Magistrates’ Court heard that the couple had enjoyed a series of dates years earlier before she cooled off on him.
Desperate to rekindle their relationship, Garnett tried to get in her good books by walking her dog and drinking in her pub.
However on December 26, he stumbled into the popular South Cliff boozer as she enjoyed a post-Christmas tipple with her son.
He was refused service due to his inebriated state but he loitered around, much to the annoyance of her son.
That spat resulted in the son and Garnett coming to blows, with the dust-up spilling onto the street.
Thursday’s hearing heard Miss Waterworth tried to step in to break it up - only to receive a punch from Garnett which damaged her teeth.
“The injuries caused her pain and discomfort,” said the Crown at the morning hearing.
“I believe that she is going to need ongoing treatment.
“Her dentist said that in the next five years she will need major restorative work or she will lose her teeth.”
In court, Garnett remained stony-faced as his solicitor Shaun Greenan declined to offer mitigation until his client’s sentencing hearing on February 18.
The court heard as part of that sentence, Miss Waterworth is seeking a restraining order against her attacker.
Magistrates stood the case down for probation to put together an “all options” report on Garnett, of Prince of Wales Terrace.
“This may include a custodial sentence,” warned the bench.
He was handed conditional bail which bars him from the pub.