Video sound to TV won't run through headphones

Hi,
I have my stereo and TV hooked up to a MacMini (the 2009 slim metal one with the optical drive). I have a headphone splitter attched to the headphones jack going to the TV and the stereo. The Mini is hooked up to the TV with a mini DP connector to a DVI-to-HDMI cable (but this same thing happens with a regular DVI cable). With my old 2,1 Mini that was fine since everything ran through the headphones.
Now I want to do the same thing but iTunes I can't get the video to run through the headphones. The only way I get sound to the TV is to run it through the HDMI output (even when using the mini DP). But then I have to manually change the sound output.
Is it possible to either:
1. Have iTunes run out the headphones jack and everything else run out the HDMI? or
2. Have everything run out the headphones output?

Info to add:
When any digital video is plugged into the Mini, the video sound only works when it's set to HDMI.
To get sound to my stereo I have to switch it to headphones. Even though I have a connector going from the headphone jack to the DVI audio input on my TV, there's no sound in headphone mode.
I tried an external USB sound card and had the same problem. Just instead of headphones it was the USB soundcard.
Maybe it's my TV...

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Video sound to TV won't run through headphones

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