A: Where’s Mary? It’s almost 11 o’clock now.

B: She’s been late for work three times this week, which is sailing close to the wind, I think.

Note: If someone or something sails close to the wind, they take a risk by doing or saying something which almost breaks rules or laws. If someone sails a boat too close to the wind, they try to sail in the direction from which the wind is blowing, and may stop or capsize as a result. This originated as a nautical expression, and has been in figurative use since the mid-19th century. Today, it’s often used when a person behaves in a way that is almost illegal or socially unacceptable.