How it all went wrong ...
Dig: In this case, means 'like'. Usually used to refer to things you find pleasant or enjoyable, or people you find attractive. (Example: She keeps looking at him; I bet she really digs him.)
Hot: Extremely attractive. (Example: There's a really hot girl in my maths class - she's got beautiful eyes.)
Play it safe: To be cautious. (Example: We're almost out of gas; we'd better play it safe and go to a gas station.)
Natural: Someone who is good at something without having to practise.
(Example: He scored a goal the first time he played. He's a natural.)