As a comedian, she often sailed close to the wind, making jokes that pushed the boundaries of good taste.
He always liked to sail close to the wind, both in his business dealings and his personal life.
He enjoyed sailing close to the wind in his sailboat, testing the limits of its capabilities.
He felt like he was sailing close to the wind, trying to balance his work and family life.
He knew he was sailing close to the wind when he confronted the bully.
He sailed close to the wind by driving without insurance.
He sailed close to the wind by exaggerating his qualifications on his resume.
He sailed close to the wind by spreading rumors, hoping to discredit his opponent.
He was sailing close to the wind by dating both sisters at the same time.
He was sailing close to the wind when he told that white lie to his wife.
He was sailing close to the wind with his health, ignoring his doctor's advice.
He was sailing close to the wind, bribing a government official.
He was sailing close to the wind, dating his colleague's ex-girlfriend.
He was sailing close to the wind, driving under the influence of alcohol.
He was sailing close to the wind, endangering the environment with his pollution.
He was sailing close to the wind, engaging in human trafficking.
He was sailing close to the wind, engaging in insider trading.
He was sailing close to the wind, gossiping about his friends behind their backs.
He was sailing close to the wind, inciting racial discrimination.
He was sailing close to the wind, inciting violence with his words.
He was sailing close to the wind, laundering money for criminals.
He was sailing close to the wind, relying on luck to get him through.
He was sailing close to the wind, sexually harassing his colleagues.
He was sailing close to the wind, stretching the truth to impress his date.
He was sailing close to the wind, taking credit for his team's accomplishments.
He was sailing close to the wind, taking unnecessary risks to prove himself.
He was sailing close to the wind, trespassing on private property.
Her actions sailed close to the wind, bordering on insubordination.
His daring driving style always seemed to sail close to the wind, narrowly avoiding accidents.
His political campaign sailed close to the wind, using controversial tactics to gain votes.
Knowing the risks, he decided to sail close to the wind with his investment portfolio.
She always sailed close to the wind in her negotiations, demanding the absolute best deal.
She knew she was sailing close to the wind when she borrowed her sister's dress without asking.
She sailed close to the wind by copying someone else's work and claiming it as her own.
She sailed close to the wind by forging her mother's signature on the permission slip.
She sailed close to the wind by telling her boss what she really thought of him.
She sailed close to the wind, betting on a horse race with borrowed money.
She sailed close to the wind, borrowing money from multiple people without telling them.
She sailed close to the wind, cheating on her taxes.
She sailed close to the wind, committing acts of treason against her country.
She sailed close to the wind, exploiting her workers for personal gain.
She sailed close to the wind, ignoring the warning signs and continuing on her path.
She sailed close to the wind, lying about her age to get into the club.
She sailed close to the wind, running a pyramid scheme and defrauding investors.
She sailed close to the wind, spreading fake news online.
She sailed close to the wind, spreading hate speech online.
She sailed close to the wind, stalking her ex-partner.
She sailed close to the wind, trafficking illegal drugs.
She sailed close to the wind, violating the terms of her probation.
She sailed close to the wind, walking home alone late at night in a dangerous neighborhood.
She sailed close to the wind, withholding information from her colleagues.
The activist sailed close to the wind, protesting without a permit.
The architect sailed close to the wind with his design, pushing the boundaries of structural integrity.
The arms dealer sailed close to the wind, selling weapons to dangerous groups.
The artist sailed close to the wind with her subject matter, challenging societal norms.
The artist's performance sailed close to the wind, challenging viewers' perceptions of art.
The athlete sailed close to the wind, pushing his body to the absolute limit.
The blogger sailed close to the wind, writing controversial opinions to gain followers.
The chef sailed close to the wind with his experimental dishes, combining unusual flavors.
The climber sailed close to the wind on that treacherous cliff face, relying on sheer skill.
The comedian's jokes often sailed close to the wind, offending some audience members.
The company's aggressive marketing strategy was definitely sailing close to the wind, flirting with false advertising.
The corrupt politician sailed close to the wind, accepting bribes and kickbacks.
The cyberbully sailed close to the wind, harassing and intimidating others online.
The daredevil sailed close to the wind, pushing the limits of human endurance.
The detective sailed close to the wind, bending the rules to solve the case.
The developer sailed close to the wind, building on land without proper permits.
The dictator sailed close to the wind, suppressing dissent and abusing power.
The entrepreneur sailed close to the wind, making deals based on handshake agreements.
The entrepreneur sailed close to the wind, taking huge risks to achieve success.
The gambler sailed close to the wind, betting everything on a single hand.
The hacker sailed close to the wind, accessing secure systems without authorization.
The influencer sailed close to the wind, promoting products without disclosing sponsorships.
The lawyer sailed close to the wind during the trial, exploiting every possible loophole.
The magician sailed close to the wind with his illusions, making people believe the impossible.
The mob boss sailed close to the wind, ordering violence and extortion.
The musician sailed close to the wind with his lyrics, exploring sensitive topics.
The musician sailed close to the wind, sampling music without permission.
The negotiator had to sail close to the wind to secure the treaty, making concessions that were almost unacceptable.
The pilot sailed close to the wind, navigating through the storm with precision.
The poacher sailed close to the wind, hunting endangered species.
The politician sailed close to the wind, making promises he couldn't keep.
The prankster sailed close to the wind, playing jokes that could have gone wrong.
The programmer sailed close to the wind, using unauthorized code to speed up the project.
The project leader sailed close to the wind, cutting corners to meet the deadline.
The project manager sailed close to the wind with the budget, hoping to stay within limits.
The reality TV star sailed close to the wind, creating drama for the cameras.
The scammer sailed close to the wind, defrauding innocent victims.
The spy sailed close to the wind, gathering information without being detected.
The stock trader sailed close to the wind, making risky investments.
The street performer sailed close to the wind, entertaining without a license.
The stuntman sailed close to the wind, performing dangerous feats that defied gravity.
The teacher sailed close to the wind, using unorthodox methods to engage students.
The terrorist sailed close to the wind, endangering innocent lives.
The vandal sailed close to the wind, defacing public property.
The writer sailed close to the wind, exploring controversial themes in his novels.
They were sailing close to the wind financially, relying on future contracts to stay afloat.
They were sailing close to the wind legally, skirting the edge of the regulations.
They were sailing close to the wind, trusting a stranger they had just met.
To get the story, the reporter had to sail close to the wind, bending journalistic ethics.