I'm fitting a headset into my TA and wondered if it was worth putting a line of grease around the outside of the cups to help it in or should i just put it in dry?

I've put the cups in the freezer over night , not sure it would help but they do it with the barings at work so anythings worth a try.

Any advice would be appreciated

Its my understanding that greased cups will slip in better than (obvious huh) dry, and its done because if you do it dry, the paint can grab the cup and chip easier. So Ive heard. A little grease cant hurt can it??

I always use grease just in case you ever need to get the cups out again. This should also remove any potential for the cups to creak once fitted.
Do you have a headset press to fit the cups?

Standard procedure at reputable Schwinn shop that I worked at for a few years:

Grease frame for headset cups, and BB cups.
Grease inside of seat tube prior to installing the post
Grease inside of forks prior to installing stem
Grease pedal threads prior to installing into crank

If in doubt GREASE IT!! Err except brake blocks I guess!

LOL!!

always grease it.

Grease is good, it also helps against rot and rust.

Go for it.

cheers lads.