I tend to agree with that sentiment. If most software "just worked", I would be okay with it from time to time. But it doesn't, so I am not. I feel the same with cutesy error messages. They're usually a bit condescending or infuriating when something is going wrong. I personally tend to be a bit clinical in my software development, despite the urge to be playful. I am also not a big fan of cutesy commit or issue descriptions either.
When I'm having problems with software I'm typically not in a whimsical mood. Most software I use are tools meant to help me do my job. A cutesy / playful error message coming from a misbehaving tool generates nothing but rage for me.
Cute, condescending error messages are unprofessional and unhelpful. If fewer programs were steaming piles of garbage I might feel differently about it.
