A hotel employee’s routine reminder to a guest about checkout time turned unexpectedly inappropriate when the man said he’d only pay his bill if she agreed to go on a date with him.

The hotel worker and original poster (OP), user Big_Air3392, recounted the incident on Reddit, explaining that the man had been staying at the hotel on a fixed-rate discount for construction workers that only applied Sunday through Thursday.

When checkout time came on Friday and his belongings were still in the room, the OP called him to inform him that he’d need to pay the regular Friday rate to stay another night.

That’s when the conversation took a turn.

“I told him it’s past checkout, and if he’s staying another night, he needs to pay,” she wrote. “He wasn’t having it.

“He got all annoyed and tried to bargain. ‘But I’ve been staying here all week!’

“Then the man twice my age goes, ‘I’ll only pay if you go out with me.’

I just said, ‘Ok, so you are leaving then?’

“Click. He hung up.

“Like seriously, does he really think I care that much about him staying here? That I’d trade a date for a hotel payment? Please.”

Reddit users flocked to the comments to weigh in, with many slamming the man’s behavior.

One remarked, “What an incredibly revolting thing to say,” while another simply added, “Ew. Ew. Ew. EW.”

Another advised, “That sounds like a perfect opportunity to contact his foreman to clarify that corporate guests are expected to behave appropriately or the group will lose its preferential status.”

“Contact his employer (or rather get your manager to do it),” one Redditor suggested.

“Explain to his boss that he acted in an inappropriate manner with staff and he may cause the company to lose their special rates etc.”

‘My manager chose not to remove him’

In a message to Newsweek, the OP wrote, “What really stayed with me was how objectified I felt like I wasn’t being taken seriously as a professional.

“The sad part is that despite the inappropriate behavior, the guest stayed, and my manager chose not to remove him.

“That made the situation feel even more frustrating.”

Inappropriate Guest Behavior

While the OP swiftly dismissed the inappropriate offer, her post drew wider attention for what it reveals about how some hotel guests interact with frontline employees—particularly women.

A 2024 article by Autohost explains that while most difficult guest behavior stems from complaints or frustration, there are rare situations when behavior crosses the line and warrants eviction.

“These are the rare but serious cases where a guest’s actions threaten the safety, security, or well-being of hotel guests and staff,” the article notes.

Hotel Staff Calling Out Inappropriate Behavior

Dealing with inappropriate or angry guests, especially when tied to issues of payment or entitlement, is a common occurrence in the industry.

“The ability to handle such guests gracefully is not just a valuable skill—it’s essential for maintaining the hotel’s reputation, ensuring the safety and satisfaction of all guests, and preserving the morale of the hotel staff,” Autohost’s report noted.

Another case of entitled behavior was featured in a July 2025 Newsweek article, which described how a guest demanded early check-in without introducing himself, instead tapping his phone on the reception window.

That same piece emphasized the growing trend of hotel staff calling out rude or aggressive behavior.

“Your front desk staff want to help you—we really do. Just don’t be a jerk about it,” the manager said.

Newsweek has contacted Big_Air3392 for comment via Reddit.

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