Man laid out 5 'terms and conditions' for a woman before their first date, claiming he wanted to be upfront — each demand got more bizarre
It’s good to communicate boundaries and expectations before a date to avoid disappointment and ensure the time is well spent. One woman, however, had a rather surprising discussion with a man before their first date. Viola, who goes by @datewithviola on TikTok, shared her horrifying tale on September 24, 2026, revealing that the guy said he wanted to be upfront and laid out five conditions for her. He noted that it was important that she agreed to each one before meeting. The problem, however, was that the conditions kept getting worse.
@datewithviola Shooketh to the core. . #datinglife #firstdate #storytime #datingstories #cheateyetalks ♬ original sound - Viola 🪻
First, the man suggested she not make a fuss about paying or splitting the bill at the time of payment. Gentlemanly? Not quite. He told her the only reason he didn’t want her doing so was that he didn't want the staff to assume he was “making you pay on a first date.” He added that she could simply split the check after they left the restaurant. The second condition was that she had to wear a certain type of clothing. He didn’t want her to wear anything too revealing and added that he thought certain colors looked better on women. He even said he had samples and would be sharing pictures. The third was similar to the second; Viola had to wear a certain type of perfume because he didn’t like all fragrances. He reportedly had “a list” from which she could pick.
The fourth condition seemed genuine until it wasn’t. He told her he’d rather she not wear makeup if she was going to end up looking different. He didn’t want a catfish scenario. However, he went on to say that she could send him a picture before she left so he could judge whether her appearance was acceptable. The fifth condition was that she shouldn’t be dramatic if he leaned in for a kiss; if she didn’t want to, he needed to be informed beforehand. Each condition was not only bizarre but also condescending. Viola noted that she was speechless after listening to what he had to say. She mentioned that she had met the man at a bar, and after hearing his peculiar list, she had to do some digging.
When she looked him up on a dating app, she realized he had very confidently and proudly listed all these requirements there as well. Disappointing was an understatement. The whole purpose of dates is to get to know the other person through gestures, communication, and clarity. However, when people choose to plan a rigid date instead of letting things flow, they compromise the outcome. Another woman ended things after her date decided to pull a test on her while meeting her for a meal.
He took her to a really expensive restaurant even after she insisted she was okay with something simple. When the hefty bill arrived, he pretended that he didn’t have his wallet and asked if she could cover the meal. She agreed, only to later learn that he was testing her to see if she was a gold digger. She confidently replied, “A provider woman provides for a king, not a man who lies about his wallet to play games.” She ended their date instantly.
You can follow @datewithviola on TikTok for more content on relationships and dating.