Prince Harry seemed to be processing his emotions after learning he would not be deployed to Iraq. While stationed for military training in Alberta, Canada, the royal took time for an off-duty evening out. During his visit, he was photographed socializing, hugging, and kissing waitresses at Cowboys Dance Hall in Calgary, a venue famous for its lively atmosphere. One of the staff members present, Cherie Cymbalis, publicly recounted her conversation with the Prince.

"He was very forward and told me I was stunning. He was really interested in my tattoos and wanted to see them more closely," Cymbalis shared. She described how Prince Harry leaned in to kiss her on both cheeks before kissing her on the lips. When asked about his personal life, she noted, "He certainly didn’t mention anything about having a girlfriend. He sure didn’t act like he had one." Reports confirmed that Harry requested her contact number and sent a follow-up text message proposing to meet after the venue closed, generating widespread media coverage of Prince Harry kissing a barmaid during his trip.

The night continued with interactions involving other venue staff. Prince Harry, then 22 years old, reportedly asked another waitress whether she was wearing underwear and remarked, "I want to see all the beautiful girls." The incident quickly became a widely discussed story about Prince Harry in Calgary, drawing significant public interest and media commentary.

At the time, commentators speculated about how his long-term girlfriend Chelsy Davy would react to the news. The episode highlighted the intense public scrutiny surrounding the royal family during private outings. Original reporting on the event was documented by the Daily Mail, while visitors exploring the city’s nightlife often look to official guides on Visit Calgary.