Should you report your boss’ workplace romance?

When a boss crosses the line with an office romance, the fallout can rock an entire company. At a Coldplay concert on July 16, the big screen panned to a couple in an intimate embrace – until they abruptly pulled apart. One hid her face. The other ducked out of frame.

Next to them, a third woman smiled in what viewers would later describe as “knowing shock”. It might have been a fleeting moment, until the Internet identified the pair as Astronomer CEO Andy Byron and the company’s chief people officer Kristin Cabot – both married, senior leaders and, very clearly, caught off-guard.

The clip went viral. Within days, both had resigned. What began as an awkward concert cutaway became a case study in blurred boundaries, leadership ethics, and the dilemma faced by those watching from the sidelines: If you knew about it, would you report it? And, more importantly, should you? Is it illegal – or just uncomfortable? Romance at work is far from new – or, necessarily, taboo.

Some even lead to high-profile partnerships, like Barack and Michelle Obama, or Bill and Melinda Gates. But when relationships occur between top executives – especially one overseeing HR – the stakes change.

One former employee, Julianne*, described dating a senior colleague in another department as both emotionally taxing and professionally disorienting.

“We kept the relationship very discreet,” she recalls. “To clarify, he wasn’t my direct supervisor, but a director in a completely different department. To my knowledge, only two other colleagues were aware.”

Still, tensions seeped in. “Things were sometimes awkward between us. We would occasionally go days without speaking.

“However, whenever I approached him for work-related matters, he was highly engaged – almost as if he felt guilty and was trying to overcompensate,” shares the 31-year-old.

This is why transparency matters. In Astronomer’s case, it wasn’t just that a CEO had feelings for a colleague, but whom he fell for, how the relationship was concealed, and what it signalled to employees.

When leadership blurs personal and professional lines, legal and ethical risks follow, says Clarence Ding, partner and Asia head of employment at Ashurst.

“There is generally nothing in the law that prohibits office romances,” he explains. “But these relationships create significant reputational risk… especially when the people involved are leaders.”

Executives are expected to model company values, Clarence explains. Their actions shape culture, and scandals at the top can drive away investors and customers alike.

“A high-profile office fling may also hurt the company’s bottom line,” he adds.

Andy’s undisclosed relationship with chief people officer Kristin, whether within company policy or not, was a liability. ‘

At best, it raised uncomfortable questions about impartiality and credibility – especially as, in real time with their immediate reactions, the two leaders demonstrated clear awareness that their actions were illicit. At worst, it posed real reputational and legal risks for Astronomer as a company.

“Assuming both parties were in a committed relationship, and the CEO had proactively disclosed it, there would be ways for the company to manage the risk,” Clarence says.

In the case of Nestle, the firing of CEO Laurent Freixe as a result of concealing his romantic relationship with a subordinate led to a drop in share prices and sales. The company stated that staff had first raised concerns about a potential relationship through its internal Speak Up reporting channel, though an initial investigation found no evidence to substantiate the claims.

According to The Financial Times, Nestle launched a second investigation with the assistance of external counsel after complaints continued, ultimately upholding the claims.

“This was a necessary decision. Nestle’s values and governance are strong foundations of our company,” said Nestle chair Paul Bulcke in a BBC report.

Whether you’re a peer, subordinate, or part of another team entirely, here are three tips to assess the situation without jumping to conclusions – or spreading office gossip.

Start with facts, not feelings

Employees should distinguish between discomfort and observable harm. “There isn’t a bright line that can be drawn between personal privacy and professional misconduct,” Clarence emphasises. “The issue is the impact that it has on the organisation.”

The risk is not always immediately visible. Clarence points to a range of liabilities: Security breaches, perceived favouritism, or conflicts of interest – especially if a partner is assessing the other’s work – can erode trust across teams. This is why it is crucial to focus on actual outcomes, not assumptions.

“That helps to prevent potential retaliation, and ensures a fair process,” adds Sonia Danani, People & Culture director, APAC at Pagegroup.

Check your companies’ policies

Many companies have written policies on workplace relationships. Some require disclosure, especially if there’s a supervisory element. Others are looser – until something goes wrong.

Julianne worked at a company with no formal restrictions. “I don’t regret the relationship, but I wouldn’t make the same choice again,” she says. “At the time, curiosity got the better of me.”

Though her relationship didn’t end badly, tensions lingered.

“My immediate supervisor, for instance, seemed to grow jealous, although they chalked it up to me being ‘good with people’,’ she shares.

“I’ve always tried to steer clear of office politics, yet I found myself right in the middle of it.”

When in doubt, speak to HR

When a relationship begins affecting team dynamics, speaking up may feel like the right move – but it’s not always easy. Reporting powerful individuals can carry social and professional risks. That’s why experts say the key is to protect yourself as much as the company.

“If no clear policy exists, or if you’re unsure, it’s best to seek confidential clarification from HR,” Sonia says.

Some companies require disclosure for risk mitigation – like reassigning reporting lines.

“Especially when it is a romantic relationship where one employee directly or indirectly supervises the other... [this] could create a conflict of interest,” she adds.

Where senior leadership is involved, external consultants may conduct investigations to ensure neutrality. Discretion is key.

“HR should discreetly gather information about the situation, including the nature of the relationship, how it became public, and the potential impact on the workplace and company’s reputation,” Sonia sums up.

The bottom line

Still, whistle-blowers can face pushback. If internal systems seem compromised, employees in Singapore can reach out to Workforce Singapore (WSG) and the Tripartite Alliance for Fair and Progressive Employment Practices (TAFEP), which provide confidential support for breaches involving ethics or power imbalances.

Not every workplace romance leads to scandal, but when power dynamics are involved, private choices can have public consequences. Whether you speak up or not, ensure that it is an informed decision – one that protects both your integrity and your career.

*Name has been changed

Additional reporting by Chelsia Tan