Cannot Hear Sounds When Changing Audio Output Devices

I have a pretty odd issue...

Lets say I have google chrome (or skype or any game such as starcraft etc.) open and I can hear the sound through my laptop speakers (Macbook Pro).

If I plug in my headset into the usb port or headphones into the headphone plug in, I am forced to restart my internet browser or whatever game it is etc.. Then I can get audio through the device I choose.

I've checked my default audio devices and reset them to whatever device I use at the time but it does no good (I also make sure that they are enabled).

**I used to be able to just have a song playing or whatever... then I could just plug in my headset or headphones and the audio would simply transfer to the new device.

Thank You!

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