Have you ever noticed that the Shuffle option on iTunes or on your iPod isn’t truly random? For example, if you have a playlist with ten tracks and start off by playing, say, the second track, iTunes will always shuffle to the exact same next track, everytime.

Doesn’t seem much like “Shuffling,” does it? It is, though: Apple’s just thinking about Shuffling a different way than you are.

I have always loved the idea of the iPod Shuffle — an iPod small enough to attach to my keychain and always carry around with me — but unfortunately, the iPod Shuffle just doesn’t fit the way I listen to music. I don’t want to randomly listen to a bunch of tracks — if I want to listen to random music, I want it curated by a DJ or something.

My Shuffle, then, rarely gets used unless I dust it off along with a delusion of jogging. But musician Matthew Irvine Brown’s new project is enough to make me want to pull my old Shuffle out of the drawer: he’s compiled a set of 18 original tracks that are meant to be played in random order on the iPod Shuffle.

Apple has removed the Chatroulette-like app, iChatr, from the App Store because of flashers.

Apple pulled the app this weekend after eight days because users were inappropriately exposing themselves to strangers while using the app.

Wow I heard rumors this was going to happen, but I thought we would end up with a web app. Instead we’ve got a new free iPhone 4 app (iTunes Link) that kind of resembles the famous Chatroulette website. Sorry, but it doesn’t work on other iPhones since it uses the new front facing camera to set you up with a random chat between users.