Jack when i plug in the headphones into the jack and listen i can only hear it on 1 side even when i have brand new headphones and when i twist the headphones when inside the jack or take it out a certain way it automatically pauses(and i dont even touch the pause button)

When you move the headphone plug around and the sound cuts in and out that usually means that the terminals in the jack have corrosion on them. You can usually clean the jack with contact cleaner that is sold in home improvement stores.

Here's a video showing how to clean the headphone jack on a phone but the process is the same for any device that uses a headphone.

Sounds defective to me.. Most stores have a 30 day return policy. After 30 days contact the manufacturer.

Just get a headphone jack that does not shut off the speakers and have your dad plug his headphones into that.

I dont think the JACK is the problem, I suspect a bad headphone wire (intermittent) or an incorrect driver, headphone jacks in laptops are software controlled, (no mechanical switch inside) if you hear sound in both the headphones and the speakes it is a driver issue, try updating the driver, if the headphone wire is erratic it can fool the software that controlls the input and do crazy things also...

Good luck!

If you click my user name you will find a tip about headphones and how to repair the jack.

Plug another headphone in walkman to check wither headphone jack in walkman is damaged or its headphone plug.
If other headphone gives same problem then open walkman and re-solder headphone jack in circuit.
Hope this will solve your problem.

I had this very same thing happen to me yesterday after listening to music with my headphones. After unplugging them, the speaker would no longer work nor the speakerphone.

After trying many things without success, I was finally able to resolve this by plugging back in the headphone cable and pushing the jack around a little bit to the side until I could hear sound.

I did this while trying to place an MP3 just to make it easier. So far this has worked fine. But now I am reluctant to use the headphones any more.
I know your post was several months ago so this may or may not be helpful.

You probably plugged a headset that does not have a mic. after you unplug it your phone will think that the head set is still plugged in. these phones are stupid and after you unplug the headset it will still be looking for the mic. Plug in and out the headset rapidly and then your phone will give you a notice saying that there is no mic to the headset. this will fix your problem. P.S. keep insisting, this fixed my problem

I agree with Solution 5. The copper pins in the jack that make the connection to your headphone plug are bent in such a way that they are springy and will make a good tight connection to the plug. When those copper connections get worn, they are not so springy and they bend inward causing you to lose audio on one side of your headphones unless you wiggle the plug and find that sweet spot that makes a connection. Then you have to hold the wire to keep pressure on it... it gets annoying.

You can open the case and there are slots in the headphone jack that you can get a hook scribe (like the dentists use) or safety pin to bent those copper connections back out. Don't bend them too far or they will break. You can also pick get a new part for $25 or a used part much cheaper. Once you iPod is open, it's a matter of a couple screws and a ribbon cable to replace the jack. Problem solved!

I had the same problem but i got the same brand of headphones as my Zen and now it works perfectly