At about 9.30pm on July 24, while ordering a second round of beers, he made contact with a waitress' breast area while trying to pay. The contact was captured on CCTV.
"It was all really innocuous," the family spokesman said.
"Jeff is a bit of a convivial joker, he always likes to entertain, and he was pretty excited to be on holiday with his family.
"He was pulling change out of his pocket to pay the lady and she's waiting there. You can see him rummage around in his pocket for more money, and laughing with his father-in-law, and I know that he'll be joking, 'Don't be so mean', and he reaches out with the change and makes contact with her breast area.
"There was nothing lewd. It just looks like a dumb, inadvertent act."
The Kiwis stayed at the bar until, about two hours later, the 39-year-old woman's angry husband arrives at the bar and police are called.
Shearer was arrested, taken into custody, and released on bail the following day.
Poor local legal advice, the family spokesman said, suggested he offer to make a reparation payment.
However, the offer was declined by prosecution and the summary of facts that went before the courts this week was not contested.
Shearer pleaded guilty on November 10 to outraging the barmaid's modesty.
The court heard that Shearer "continued to try and touch the woman, who fended off his attempts", the Strait Times reported.
The prosecution claimed that his actions were "chauvinistic and completely demeaning" to the woman.
But Shearer's family believe it overstates the situation, saying it was "at worst, just very dumb".
The Strait Times reported District Judge Dorothy Ling telling Shearer: "A message must go out that service staff must be treated with respect."
The jail sentence is not backdated.
From when he was arrested on July 24 to being jailed on Thursday, Shearer has been living in a rented apartment, unable to leave the country.
His wife Kerry is distraught and back at home with three children aged 3, 5, and 7.
The family spokesman spoke to Shearer yesterday.
"He's a bit of a shambles," the spokesman said.
"He's lost about 11kg through stress and his blood pressure is through the roof. He's never been involved in any legal issues before. It's a massive shock to him."
The New Zealand Ministry of Foreign Affairs and Trade (MFat) said the New Zealand High Commission is Singapore is providing consular assistance to Shearer.
"Due to privacy considerations no further details will be provided," a MFAT spokesman said this morning.
The case has parallels with that of a Scotsman who was sentenced to three months in a Dubai jail for touching a man's hip this year in a crowded bar.
Jamie Harron, 26, was later freed after ruler of the emirate Sheikh Mohammed bin Rashid Al Maktoum made a special order for the case to be dropped.
The family spokesman said New Zealanders needed to be aware of other cultures and judicial systems while abroad.
"There's a level of naivety from an inexperienced traveller in a foreign environment where the rules are different," he said.
"We all know Singapore and its severe judicial rulings - dropping rubbish and chewing gum can get you in a lot of trouble - but having said that you need to understand that when you travel to those places."
