In the past, waitressing at exclusive summer events such as Henley and Ascot involved navigating challenging guest behavior, including unwanted physical advances and intoxication, according to a former hospitality worker.

During the 1990s, waitstaff were expected to serve affluent patrons at these high-society gatherings, often for low wages, while enduring interactions with guests who would sometimes offer money inappropriately. One recollection from an event at Henley involved a guest exhibiting signs of cocaine use, indicated by white powder on his cheek and dilated pupils, while appearing to party excessively.

Waitstaff at these events often faced demanding conditions, sleeping in campsites between shifts. Anecdotes include humorous instances of cooling feet in ice buckets before serving drinks with the same ice, or strategically miscounting food portions, like beef at Ascot, to manage shortages caused by guest demands or over-serving. A particularly awkward incident involved a guest receiving a quail directly into his lap, leading to his demand for the waitress's dismissal, though she was not fired.

Beyond the daily challenges, the industry had strict policies. One former staff member recalled a colleague being denied leave for a stomach ache, only to be later diagnosed with acute appendicitis after finishing her shift.

The described environment was not limited to lewd behavior and intoxication. On one occasion at Ascot, waitresses were reportedly paid to leave a private box for several hours where a group of bankers had invited escorts.

The author, Annie Hayes, who is returning to Henley as a paying guest, expressed a newfound empathy for service staff and a commitment to treating them with courtesy, noting that good manners cost nothing and contrasting them with potentially risky guest behavior.