Enna Clark played a few rounds and finally found the trick, no longer losing every time.
However, this Monopoly game is completely dependent on luck, unless you're someone who can control the number of points you roll. Otherwise, it's all about luck.
And to avoid any tricks with the dice, usually, it's the female companion brought by the man who rolls.
For example, Olivia and Adam Sinclair had Olivia playing, Rupert Harris and Emily Goldsmith had Emily playing, and the others also had their female companions participate.
Some companions were obviously just brought out for fun, and they would become particularly nervous during the game, afraid of losing money and displeasing their patron.
However, anyone acquainted with Rupert Harris is usually quite well-off, so even if they lost money and felt slightly unhappy, they wouldn't show it on their face. At most, they might give some advice on how to roll.