He wanted romance. But she only wanted friendship.
And when Nora Tan Shu Mei rejected his advances, K Kawshigan sued her for $SG3 million ($3.24m) in Singapore's High Court, citing the emotional trauma he claimed to have suffered.
The CEO of a drone-racing company who is about 30 years old said he first met Ms Tan at a social event in 2016.
Over time a friendship developed, but in late 2020 the pair "became misaligned" about how they saw their relationship, according to court documents.
The documents reveal she eventually told him she only wanted friendship.
"In the discussions that followed, [she] requested for their interactions to be reduced," according to a court transcript.
"This caused displeasure to [Mr Kawshigan], who felt that this would constitute 'taking a step back in the relationship'."
When Ms Tan then tried to impose boundaries and restrict contact with Mr Kawshigan, he threatened legal action for "monetary damages arising from negligent infliction of emotional distress and possible defamation".
The woman sought to reason with Mr Kawshigan, urging him to be "self-reliant" and telling him her "discomfort" was genuine.
In response, he told her she could comply with his demands or suffer "irrevocable damages to [her] personal and professional endeavours".
"Your discomfort is as fake as the cause," he responded in one phone message.
"And emotionally, till the day I die, you are the cause of my trauma."
How the dispute ended up in multiple courts
Despite the threats, Ms Tan agreed to take part in counselling sessions to "help [Mr Kawshigan] come to terms with her decision to not pursue a romantic relationship with him".
But 18 months later, she felt the sessions had become "meaningless and futile" because Mr Kawshigan had appeared "unable to accept her reasons for not wanting any relationship or association with him".
In the face of his "repeated demands for more frequent meetings and deeper conversations", she cut all contact with him.
She obtained a protection order against him, and has since lodged harassment proceedings for damages, covering costs she has incurred to pay for extra security at her home, as well as personal counselling.
He lodged a High Court lawsuit against her, asking for $3 million to cover "indefinite loss of potential investment, rehabilitation and therapy programs to overcome the sustained trauma, as well as reductions in his earning capacity".
In a separate case, Mr Kawshigan also sued Ms Tan in Singapore's Magistrates Court for $SG22,000 in damages, claiming she had breached an alleged agreement between them to "improve their relationship".
With legal cases looming, Ms Tan had offered Mr Kawshigan a list of "improvements" she could make to their relationship, including "meeting up based on mutual availability beyond coffee settings" and "room for [him] to share inspiration, struggle and achievements".
But last month the Magistrates Court ruled there was no such binding contract, and struck out Mr Kawshigan's claim as an abuse of process, describing it as "manifestly groundless and without foundation".
"Considered in totality, I find that the present action was intentionally initiated by the Claimant (Mr Kawshigan) with the ulterior motive of vexing or oppressing the Defendant (Ms Tan) by requiring her to defend various claims," the magistrate wrote.
"This court will not be an accessory to his calculated attempt to compel engagement from the Defendant who, after years of massaging the Claimant's unhappiness, has finally decided to stand up to his threats rather than cower and give in to his demands."
But the High Court case is still ongoing, as is Ms Tan's harassment claim.
His High Court case will be back in court on March 2.
The ABC has tried to contact Mr Kawshigan for comment.
'Women do not owe men their time'
A Singaporean women's rights group says the litigation paints "an alarming picture of male sexual and romantic entitlement" even after a woman has communicated her discomfort and lack of interest.
"Women do not owe men their time or attention, much less their friendship, love, sexual activity or emotional labour," Aware Singapore said in a recent statement.
"Concepts such as the 'friendzone' — which implies that women should by default be sexually attracted to the men in their lives — are part of this spectrum of male entitlement.
"We need to dismantle toxic masculinity and the patriarchal mindsets that underpin this behaviour."
Singapore enacted a Protection from Harassment Act in 2014 to protect people from being targets of harassment or stalking, both online or in real life, with possible jail terms of up to six months or fines of up to $SG5,000 for breaches.
But a study five years later found harassment of women was still common.
The survey found a quarter of Singaporean women had experienced sexual harassment, almost half of whom failed to report it out of embarrassment or for fear of repercussions.
Among the most experienced forms of sexual harassment, 27 per cent involved persistent and unwanted invitations of a sexual nature.
