Just try connecting the plug quickly.
I faced similar issues until it was solved by just making one quick swipe into the connector everytime i neeed to connect the headset.
2011-02-14 8:13 - edited 2011-02-14 8:14
Yes, do as Harish said. Insert it quickly in one clean motion.
If you did it right, the n8 will recognize the device as a Headset. If you were too slow, it might mistake it to be a Headphone