High Court rules lavish spending was largely gifts, rejecting claims they were repayable loans.

A bitter breakup has ended in a courtroom defeat for a company chief executive after Singapore’s High Court rejected his attempt to recover hundreds of thousands of dollars spent during a romantic relationship.

CEO Sues Ex-Girlfriend for S$468,090
Chander Agarwal, chief executive and managing director of India-listed logistics company TCI Express, sued former girlfriend Felicia Lee after their relationship ended in December 2023, seeking to recover S$468,090 he said represented loans. The couple began dating in September 2022 after first meeting on a flight in 2019. Agarwal filed the lawsuit in March 2024 after the relationship deteriorated amid his suspicions that Lee had been unfaithful. On September 9, 2026, Singapore’s High Court dismissed his claim.

Court Finds Spending Was Largely Gifts
Senior Judge Lee Seiu Kin found that most of the disputed spending had been voluntarily given as gifts rather than loans. The sums included around S$206,000 in credit card expenses, S$129,000 for overseas travel, S$17,000 for a feng shui master, and S$30,000 for a Stanford-NUS executive program. Agarwal also failed to prove that he had provided two other claimed sums, including S$50,000 he said was meant to settle Lee’s debt to a former employer.

Messages Undermine Repayment Claim
The court found no evidence showing that Lee had requested the disputed spending as loans or agreed to repay it. Instead, messages produced during the proceedings showed Agarwal repeatedly encouraging her to use his money. When Lee once asked how she could repay him, he responded that there was no need and said he was not a moneylender. He later offered her S$1,500 a month for expenses and access to his American Express Centurion Card without a stated spending limit.

Handwritten Agreement Given Little Weight
Agarwal relied on a handwritten document that he said had been signed by Lee and indicated that money she received belonged to him. Lee denied signing or seeing it before the court case. The judge considered the circumstances surrounding the document suspicious, particularly because Agarwal did not mention it in his original statement of claim and introduced it only seven months later. A separate note signed by Agarwal in May 2023, promising not to seek the return of items given in goodwill, was also found to supersede any earlier arrangement.

Judge Rejects Transactional Relationship Argument
During cross-examination, Agarwal argued that once the pair became romantically involved, his spending automatically became transactional and should be treated as loans. The judge rejected that position as inconsistent with common sense and with Agarwal’s own messages and behavior. The court also dismissed his claim that Lee had induced him to spend by falsely presenting their relationship as genuine and exclusive, noting evidence that Agarwal himself had sexual relations with other women during the relationship.

The case highlights the legal distinction between gifts and loans in personal relationships, particularly when large sums are exchanged without clear repayment agreements. For Singaporeans, the ruling is a reminder that courts rely heavily on documentary evidence, conduct, and communications when deciding private financial disputes. Indonesians with personal or business ties in Singapore may draw a similar lesson: significant transfers between individuals should be clearly documented when repayment is genuinely expected.

Sources: Asia One (2026) , Straits Times (2026)

Keywords: Singapore CEO Lawsuit, Chander Agarwal Case, S$468000 Girlfriend Lawsuit, Singapore High Court, Relationship Gifts Singapore, Loan Versus Gift