← All confessions · Officevia Ask a Manager / The Cut 2026-10-13

The Boss and the Coworker

Everyone suspected the boss and their colleague. Then he sold his house and made it official.

How it started

In a workplace romance edition of her advice column, written during The Cut's 'It's Complicated' week, Alison Green of Ask a Manager tackles a tangle of office love questions. One reader explains that for years the office whispered that their manager was secretly seeing a co-worker who reports directly to him, despite the boss having a long-term partner at home. Then, in quick succession, the boss split from that partner, sold his house, moved into a city apartment and officially started dating the colleague. The rumours were confirmed. The owner of the company knew and didn't seem bothered. The reader loves their job and likes the boss, but feels uneasy about fairness and favouritism and wants to know what to do.

Then it happened

The column works through the reader's options alongside other dilemmas, from crushing on a colleague to asking an old date for a job referral. The gist: a manager dating a direct report creates real problems for everyone else on the team, even when the couple are happy.

The morning after

The couple went public, the owner shrugged, and the rest of the team was left whispering by the coffee machine. Readers piled into the comments with their own boss-dating horror stories. The rumour mill, it turns out, had been right all along.

Read the original on Ask a Manager / The Cut ↗