Searching scaffolding 16 floors up in high wind - and suffering from vertigo...

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Scariest thing I've ever done..

I think that expressing your feelings towards a girl would always qualify, although that is another 'sort' of scary though :p
Well to say reallllly on topic I'd say.. confrontating highly aggressive psychiatric patients. Always unpredictable.

Must say that I haven't done that much scary things yet.. my mind stays quite clear when thinking of something.. :p

For me, it would be going up Cypriot mountains with vertigo and breathing problems and dealing with the results or having a lumbar puncture performed on you or being in charge of pyrotechnics at a school show for the first time or facing my phobia (which is dreams... lol ).