‘Curiosities and dilemmas’ looks at some unusual probabilistic phenomena, before applying probability theory to modern day issues. It is accepted that a game which favours the house cannot ever favour the player. However, Parrondo's paradox comprised just such a game, which was reconciled into a mathematical formulation proving the house always wins. Simpson's paradox shows the perils of working with proportions rather than absolute numbers. An individual's probability to develop a disease is now highly predictable thanks to genetics. This can provide painful life choices for families, or potentially lead to discrimination from insurers. It is important to remember in these situations that probability does not equal certainty.