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it may be that you have the repeat option turned on and dont know it. try going into options or where ever the repeat option is located and switch it off. you also might want to try and select a different song in the album to see if the repeat is on. hope this helps
you have to hit play again after you unplug the headphones and turn the volume up using the buttons on the left side of the device, if you have no buttons on the left side then you have the 1st Gen iPod touch which you can only listen to with headphones.