The Employment Relations Authority found the woman, who cannot be named, was unjustifiably dismissed from her administrative role at the small business.
Her boss told the ERA she was never employed and only did work at the business "as his girlfriend".
The ERA took the unusual step in ordering permanent non-publication of any identifying factors because of the adverse health effects on the woman - referred to as "N".
She was initially involved in a consensual relationship with the man - referred to as "S" - in early February 2019. This led to her being employed at his small business from mid-February.
The man bought a phone for her and said she could pay it off - and he would help her buy a car - if she worked for him.
N said she worked part-time for S and was paid in cash and goods but was not given a formal employment agreement.
The woman said she was uncomfortable continuing the relationship with S after she started working for him but told the authority she "had difficulty persuading S to this viewpoint".
S disputed that N was an employee and said she visited his workplace with a friend to "hang out" and that any money and goods he gave her were in the context of their personal relationship.
He admitted N had asked him "for a job" and indicated he would consider this but said it was "unlikely I would employ her as I considered her a girlfriend only".
In March 2021, the pair had a "significant argument" and S said he "wanted nothing to do with her and she should not return to his workplace".
N's employment advocate contacted S in April and said they considered N had been unjustifiably dismissed.
S responded and said N had never been employed and said he had considered offering her a job but their personal relationship had broken down so he had "cut communications with her".
Evidence that S purchased a cell phone for N and suggested he could help N buy a car with her paying it back by working for him was indicative of an employment arrangement.
N said she worked at administrative tasks such as ordering components via email, phone calls, and cleaning duties.
A friend of N confirmed she had looked after N's children when she was "at work". The same friend said she observed N in the office answering phone calls and sending emails.
N said she dressed tidily to attend work but S said this was because he told her "to dress nicely as she was hanging out with me".
The ERA said there was no evidence that N's work was integral to the business but did find N had performed work duties.
The ERA concluded N was an employee given S conceded he was considering formalising the work agreement.
It found there was a "clear imbalance of bargaining power between parties" and described S as a "mature and experienced businessman engaging in a personal relationship with a young, unemployed and vulnerable woman to whom he was holding out the prospect of long term employment".
N also told the ERA she felt sexually harassed at work because S was intimate with her in the workplace through suggestive comments and physical touch.
She found this uncomfortable and told S she wanted to de-escalate the relationship to one of friendship but S did not take this well.
N said S turned up to her house after work hours and "became physical and grabbed my head and physically turned it toward his face and tried to kiss me". She said this was humiliating because it was in front of a friend.
N also claimed a friend of S had visited the workplace and discussed, in her presence, how he took sexually explicit videos of a woman he was dating.
N was so uncomfortable about this she told S and left the workplace upset.
S then insisted N drive that friend to a house and on the way he physically assaulted her by putting his hand on her thigh. He stopped after she swore at him.
The ERA said it was hard to conclude there was sexual harassment but said there was evidence of unwanted sexual discussion that was not ideal and "exacerbated N's distress".
It was not clear if N had told S about the sexual incident in the car with his friend.
The authority found N was unjustifiably dismissed because S gave insufficient attention to any procedural requirements before ending N's employment after their personal relationship ended.
The reason for ending the employment and brief personal relationship was that S quickly wanted N out of his life.
N was awarded three months of wages (30 hours a week at $17.70) and $18,000 in hurt and humiliation.
The ERA awarded the full compensation requested as N gave compelling evidence of the impact of the dismissal during an exceptionally difficult period of her life.
She felt depressed and anxious and socially isolated and the impact and circumstances of losing her job made her feel worthless and affected her confidence.
The ERA found N was "afforded no dignity and suffered significant humiliation as a direct result of how she was dismissed".
N felt S had "dispensed with her services in a callous fashion and the situation was made worse by S ignoring personal boundaries N tried to impose".
