Question Can I use my headphones with a subwoofer?

Math Geek

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my desktop speakers are a 2.1 set-up. my audio output goes to the subwoofer and then a 3.5mm jack outputs to the 2 speakers.

never even thought of it, but might be able to plug headphones into that sub output and have it work like you are thinking (or at least what it sounds like you are thinking). sub would do its thing and the rest would go to the headphones.

again never even considered such a thing, but the theory sounds right. otherwise, you'd have to have separate outputs for each. no idea how that would wire or if it would or would not work, but that would be the basic idea.
 
It will work. For that you need "OPEN BACK" headphones. DSP like Mini-DSP to split the signal properly between 2ch speaker/headphone high pass signal and routes low-pass sub signal to subwoofer.

But seriously very odd and not optimal. Because headphones like good ones can go down to SUB frequency range. Still if you want to feel SUB rumble then going for speakers over headphones will be much better.

If you still want to go Headphone + SUB route then yes it is possible. Get MiniDSP Flex. Then connect the High Pass signal outputs to Headphone AMP and Low Pass output to SUB.

Yes you need to use Open Back Headphones for it to work as you need that sub to leak into your head phones.

Would recommend getting speakers if possible.