Court Cases & Orders

The “Sugar Daddy” Lawyer and the 18-Year-Old: Did His $226 Million Lawsuit Have Merit?

Written by Russell Alexander / (905) 655-6335

In the realm of Family Law, some relationships are what you would call “untraditional”. And when they end, they sometimes wind up in litigation – but not for the usual reasons.

The “Sugar Daddy” Lawyer and the 18-Year-Old

In a recent Ontario ruling, the court introduced the back-story between a man and a young woman this way: 

The [woman] was 18 years of age when she met the [man] who was about 30 years of age, on a dating website called “Seeking Arrangement”. The website is described online as a premier dating website for sugar babies and sugar daddies. Sugar dating is also called sugaring, which is a transactional dating practice typically involving an elder wealthier person and a younger person who needs financial assistance.

The man was a lawyer and had an MBA degree, and he worked at a Toronto investment bank.  The woman’s part of the arrangement was described by the court this way: 

[The woman] described her understanding of their relationship was that she would keep [the man] company, “virtually”, listen to the stresses of his schooling and job and provide friendship via phone, email, and text. The relationship started in May 2016. [The woman] asked [the man] for money to assist her with various expenses, including rent, using his Uber Eats and Uber accounts on a regular basis.

Over a three-year period, the woman and man only met in person once, but they did communicate by text and the odd phone call.  But the man started to become accusatory, abusive and possessive over the woman.   He understood her to be his girlfriend, and stated he was in love with her.  He kept pressuring her to meet.

This made the woman anxious, and she started to make up excuses not to see him. She claimed she had a broken leg, and that she was being treated for cancer – both of which were untrue.   She eventually told him she wanted no further contact, and blocked him from social media, but he continued to contact her using fake social media accounts.

This is where things took a turn.  The man threatened to ruin her reputation, and called her harsh names like “whore”.  The court continued:

[The man] did not accept [the woman’s] termination of their relationship. He continued to send her more money, which she refused. He became obsessed and very angry with [the woman] and started contacting her family, friends, and professional contacts. He also followed her social media account and contacted her new boyfriend. [The man] also wrote emails to [the woman’s mother’s] business contacts complaining about [the woman’s] disgusting behaviour of fraudulently scamming him.

Did His $226 Million Lawsuit Have Merit?

Eventually, the man sued the woman and her parents for $226 million, alleging fraud, defamation, interference with his economic interests, intentional infliction of emotional distress.  He claimed the woman’s lies had prompted him to send her money. 

The woman applied to have the man’s case thrown out, on the ground it was frivolous, vexatious, and had no merit, and because it was past the two-year deadline for bringing a claim in the first place.

The court examined the unusual facts, and agreed with the woman’s position. 

First of all, the time-limit on the man’s potential claims had indeed expired.   He had known about the woman’s false excuses as early as 2018 and – especially as a lawyer – would have known that commencing an action against her would have been the appropriate way to obtain a remedy. 

Next, the court ruled that the man’s claims against the woman and her parents were completely without merit.  He found the woman on a “sugar daddies and sugar babies” dating site, and would have reasonably expected to make some payments to her. As the court put it simply, “He was disappointed with the extent of their relationship and became obsessed with [the woman] when she ended their relationship.”  This was not the basis for a valid legal claim.

The court added that the man’s 340-paragraph statement of claim, which claimed exorbitant damages of $226 million, had the hallmarks of a vexatious proceeding.  This is considered an abuse of the court’s process.

After granting summary judgment in the woman’s favour, the court ordered the man to pay her and the family $15,000 in costs. 

(As a post-script: The Law Society of Ontario recently imposed a professional suspension on the man, which prohibits him from practicing law for a month.  This stemmed from a complaint by the woman’s lawyer who she had hired to defend her against the man’s claim.  The lawyer gave evidence that the man persistently called him “crazy” and a “strip mall lawyer”, demanded proof of his accreditation, circumvented him by writing to the woman and her family directly. He also threatened criminal charges against him, among other types of professional misconduct).

Full text of the decision:

Rahmal-Shah v. Jones et al., 2023 ONSC 820 (CanLII), <>

Details of the one-month suspension by the Law Society:

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About the author

Russell Alexander

Russell Alexander is the Founder & Senior Partner of Russell Alexander Collaborative Family Lawyers.