I've done quite a few things which turned out to be daring, but as they just sort of happened and weren't exactly planned I don't think they can count. The biggest planned most daring thing I've done has to be having 3 children in under 4 years. But even that didn't seem daring at the time.
Thomas Markle Snr. being investigated for child sexual abuse images.
Sadiq Khan has commissioned benches from Spain for the pedestrianised Oxford Street
Thinking about it, much more scary than parapenting, snowboarding or naturism 