Singapore Court Rejects CEO’s S$468,000 Ex-Girlfriend Claim

Published: 11 September 2026. The English Chronicle Desk. The English Chronicle Online

A Singaporean businessman who sought to recover almost half a million Singapore dollars from his former girlfriend after their relationship ended has lost his case, with the High Court ruling that the money was given as gifts rather than loans.

Senior Judge Lee Seiu Kin dismissed Chander Agarwal’s claim for S$468,090, finding that the evidence showed a man who had willingly spent large sums on a woman he was romantically involved with, rather than a creditor expecting repayment. The judgment was issued on 9 September 2026 in the General Division of the High Court of Singapore.

The case attracted attention because of the scale of the spending and the circumstances surrounding the dispute. Agarwal, the chief executive and managing director of publicly listed Indian logistics company TCI Express, had met Felicia Lee, a former flight attendant, on a flight in 2019. They later developed a relationship and became romantically involved from September 2022 until their breakup around December 2023.

The relationship began after Agarwal had already started giving Lee expensive presents. According to the judgment, the businessman had established a pattern of spending generously on her even before they became a couple.

During their relationship, that spending continued.

Agarwal subsequently argued that many of the payments were not gifts but interest-free loans that Lee had requested and was obliged to repay. His claim covered a range of expenses, including substantial credit-card spending, overseas travel, life-insurance premiums and other personal expenses.

The precise figure before the court was S$468,090. The claim included about S$151,658 in personal expenses charged to Agarwal’s American Express Centurion card, around S$31,000 on an American Express corporate card, approximately S$20,000 in life-insurance premiums and nearly S$20,980 in expenses charged to a Citibank card. He also claimed S$50,000 that he said had been provided to help Lee settle a debt with her former employer.

Other disputed spending included money for overseas trips and a feng shui consultant for Lee’s apartment. The overall spending demonstrated the unusually generous financial arrangement that existed between the couple.

But the central legal question was not whether Agarwal had spent the money. Both sides accepted that he had. The issue was whether the payments constituted enforceable loans or voluntary gifts made during a romantic relationship.

Lee maintained that they were gifts given out of love and affection. She disputed the suggestion that she had repeatedly approached Agarwal for loans.

The judge ultimately agreed with her interpretation.

Agarwal was unable to produce sufficient documentary evidence demonstrating that Lee had requested the disputed payments as loans or had agreed to repay them. The court also considered the conduct of the parties and the way they communicated about the money.

The evidence, the judge concluded, was inconsistent with Agarwal’s later description of the spending as a series of loans.

A particularly important issue was the absence of clear acknowledgement by Lee that she had received loans requiring repayment. Agarwal relied on a handwritten document in which Lee purportedly acknowledged receiving money from him and said it belonged to him. But the court considered the circumstances surrounding the document and the wider evidence rather than treating it as conclusive proof that all the disputed payments were loans.

The judge also found that Agarwal’s conduct during the relationship was more consistent with generosity than ordinary lending.

In the written judgment, Lee Seiu Kin described Agarwal as “smitten” and said the evidence showed that he had “showered her with expensive gifts”. The judge noted that Lee sometimes appeared surprised by the value of the gifts and on occasions expressed reluctance to accept them.

That evidence mattered because a court deciding whether money was a loan or a gift cannot simply look at the amount transferred. The surrounding circumstances, communications and the parties’ apparent intentions are also relevant to determining whether an enforceable obligation to repay existed.

The judge described Agarwal as a man of substantial means with expensive tastes, while noting that Lee was not in the same financial league. That difference helped provide context for the spending pattern during their relationship.

The relationship eventually deteriorated after Agarwal suspected Lee of being unfaithful. Their romantic relationship ended in December 2023, and Agarwal commenced legal proceedings in March 2024.

The timing became significant in the court’s assessment of the dispute.

Rather than viewing the financial transfers in isolation, the judge considered the possibility that the breakdown of the relationship had altered Agarwal’s interpretation of what had previously been willingly given.

The judgment concluded that the evidence showed a pattern of generous spending during the relationship, followed by an attempt to recover the money once the relationship had ended badly. That did not establish a legal basis for treating the gifts as loans.

The case is a reminder that romantic generosity and legally enforceable lending are not necessarily the same thing. A person who spends substantial sums on a partner may later regret those decisions, particularly after a difficult breakup, but regret alone does not transform a gift into a debt.

For wealthy individuals in particular, the judgment highlights the importance of documenting the nature of substantial financial transfers when repayment is genuinely expected. Without clear evidence that both parties understood the money to be a loan, attempts to recover it later can become legally difficult.

The Singapore case also recalls another unusual relationship dispute that reached the country’s courts.

In 2022, K Kawshigan brought two lawsuits against Nora Tan after their relationship broke down. One claim, filed in the Magistrate’s Court, sought S$22,000 and alleged that Tan had breached an agreement concerning their relationship. A separate High Court action sought more than S$3 million, including damages connected to alleged emotional trauma and reputational harm.

The Magistrate’s Court struck out the S$22,000 case, describing it as an abuse of process and finding that the court would not assist what it regarded as an attempt to compel Tan to engage with Kawshigan.

Tan subsequently brought her own claim for expenses she said she had incurred to protect herself, including security equipment for her home and counselling-related costs. The dispute became one of Singapore’s most widely reported examples of a failed attempt to use civil litigation to address the consequences of a rejected romantic relationship.

The Agarwal case is different in its legal substance, but both disputes demonstrate how complicated the boundary between personal relationships and legal obligations can become when significant money or alleged damages are involved.

In Agarwal’s case, however, the High Court’s reasoning centred on intention.

A relationship may involve expensive dinners, holidays, insurance payments, luxury purchases and other forms of financial support without those transactions automatically creating debts. Where a person voluntarily provides such benefits without clear evidence of an agreement for repayment, a later attempt to recover the money can face substantial obstacles.

The court’s conclusion was therefore not simply that Agarwal had spent too much money. It was that he had failed to prove the legal character he later assigned to that spending.

The judge ended the written judgment with a reference to William Congreve’s famous line about love turning into hatred, adding that such emotion is not the exclusive province of either gender. The remark provided an unusually literary conclusion to a case that had begun as a dispute over hundreds of thousands of dollars and ended with a finding that the money had been given, not lent.

For Agarwal, the outcome means the S$468,090 he sought to recover will not be treated as a debt owed by his former partner. For Lee, the ruling confirms that the substantial expenses she received during the relationship cannot simply be reclassified as loans because the relationship later ended on hostile terms.

The broader lesson is straightforward. Lavish spending during a relationship may be generous, impulsive or even unwise, but generosity does not automatically create a right to repayment.

When a relationship ends, emotions can change the way past events are remembered. The Singapore High Court has now made clear that changing emotions cannot, by themselves, rewrite the legal nature of financial transactions that took place while the relationship was intact.

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