Oh tough one! I guess ultimately hair grows back... and if you have never had it short why not take a risk and be daring? it will be easier to maintain and feel so much lighter and cool...
In saying that, I have long hair too(past boobies) and have had urge to go the chop but dp loves it and i think would probably cry if i got it cut lol....
But if you feel like a wreck going to a nice salon and treating yourself and getting a fresh new style would probably do you the world of good! Some of the flash salons even give you champagne while they cut, yippee