1) If I had to guess you are conflating two things when you say democracy. When people say 'democracy' in western countries they are usually referring to a particular form of democracy: liberal representative democracy, or also occasionally refereed to as constitutional democracy. Its quite possible to have illiberal democracies with some contemporary illiberal democracies being Egypt, Russia, Philippines, and increasingly Turkey. Democracy, in either its representative or direct form doesn't guarantee liberal values such as due process, freedom of the press, and formal or informal political oppositions.

A population can keep willing electing a dictator and that dictator could even be popular, but that political system would not be a 'democracy' as you might normally recognise; it will espouse none of the liberal values that places like the UK and the US typically expect.