TrueCrypt is one of the safest ways to store things on your HDD. Not that a HDD is a reliable place to store things in the first place. (Keep a backup on Optical). TrueCrypt also works with USB keys.
Don't store private stuff in the cloud (ie Hotmail, Dropbox etc) unless it is encrypted (eg:ZIP/RAR), because if your account gets hacked, then you will loose control of your stuff, or worse, loose your stuff altogether.
If you use WinZip / RAR then use a long password, eg 8 or more characters of a good mix.
I have pics/vids of ex's and I don't bother to encrypt it. I have a password protected PC so my wife can't get onto my login. If you share a PC, then make sure you have separate logins.
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