Zulkifly Pardon was hoping that a night of drinks would make him seem more attractive to a woman he had just met.
But when he invited Ms Murni Wati Azni to accompany him to a hotel nearby, she said "no" and pushed him away.
Incensed, he punched and kicked her in the face, and left her lying on the pavement outside Palais Renaissance mall in Orchard Road.
Yesterday, Zulkifly, 45, who is jobless, was sentenced to six months' jail after pleading guilty to hurting Ms Murni Wati, 27.
The serial offender's total jail sentence comes up to 35 months.
This includes 29 months behind bars and three strokes of the cane for other crimes - theft, harassing a debtor on behalf of a loan shark, and a drug-related offence - all committedin May and June.
The court heard that on the evening of June 15, Zulkifly had gone to Orchard Towers with Ms Murni Wati, who is also unemployed. The duo, who are both Singaporeans, downed two bottles of Chivas Regal whisky at two different pubs.
He attacked her at around 6am the next morning, and she was left with abrasions and a bruise on her head, and had to be treated in hospital. Pleading for leniency, Zulkifly said he was divorced, with two children, and that his former wife would struggle to support the family.
But District Judge Low Wee Ping noted that Zulkifly had a long criminal record stretching back to 1985, when he was just 16.
Pointing to Zulkifly's crimes committed this year, the judge said: "It looks like... you went on a rampage."
Zulkifly, who also admitted to theft and another drug-related offence, which were taken into consideration, could have been jailed for up to two years and fined up to $5,000 for voluntarily causing hurt.
For harassing a debtor on behalf of an unlicensed moneylender, he could have been jailed for up to five years and fined up to $50,000.
This article was first published on Oct 24, 2014. Get a copy of The Straits Times or go to straitstimes.com for more stories.