He proposed with a $15,500 diamond engagement ring and showered his beloved in lavish gifts including a diamond necklace, a Longines watch and a Louis Vuitton handbag.
But when romance soured and he broke off the engagement 10 days before the wedding, Edwin Shien Bing Toh demanded his former fiancée Winnie Chu Ling Su give it all back.
The Local Court in Sydney performed the relationship post-mortem as Mr Toh sued Ms Su for the return of the engagement ring, two wedding bands, five gifts and $1000 in cash.
The court heard the couple met through a mutual friend in 2015. By October that year they had opened joint bank accounts and visited a jewellery store to buy a $15,500 engagement ring and two wedding bands totalling $1300.
He proposed in December and the pair "re-enacted the scene for a photographer", Magistrate Rodney Brender said.
Days later, the couple left Australia on a trip to China and Mr Toh gave Ms Su both wedding bands "so that she could show them to her parents".
But the course of true love ended abruptly on March 5, 2016, when Mr Toh called off the engagement after three months.
At a meeting attended by his former fiancée and a friend, Mr Toh said "everything that belongs to each party will be returned to each party", and Ms Su agreed.
In that spirit, she asked Mr Toh to "take off the shoes he was wearing" because she had bought them, and he did so. She also visited Mr Toh's parents' house with her mother and took away a wallet she had given him, along with presents her parents had bought for him and his parents.
Mr Toh, through a lawyer, demanded the return of the three rings and five gifts, which also included an iPhone and a Samsonite suitcase. When Ms Su refused, he took action in the Local Court.
Mr Brender examined English and Australian cases and concluded that because it is no longer possible to sue for breach of a promise to marry, "the gift of an engagement ring should be seen as unconditional".
"Many gifts are given in happy times and with optimism. Sometimes that optimism is borne out, sometimes it isn't. Why would the law treat a gift of a ring between same sex couples as different? Or between couples who give a ring in anticipation of a de facto relationship starting and prospering?" he said.
The gift could be made conditional by "words or conduct" but "here there were none". He refused to order the return of the engagement ring.
He also refused to order the return of the gifts, saying the "brief exchange of words" between the couple in a "domestic setting" did not constitute a contract.
Mr Brender said Mr Toh agreed to Ms Su's "emotional demand" to return his shoes because she asked him to, rather than because they had a contract, and he "may have felt a little guilty for breaking off the engagement 10 days before the wedding".
But the magistrate concluded the two wedding bands were in a different category because they were bought "in contemplation of marriage". Ms Su was given them for "safe keeping" but they remained Mr Toh's property.
Mr Brender ordered her to return the wedding bands and $1000 in cash from a joint account.