I recently had my hair cut to my shoulders after having it at waist length and i really dont like it! It was originally down to my bum but everytime i went to the hairdressers i went shorter and shorter! I regret it so much... i just want my hair to grow back, and fast!
Seriously, I'd take the chance to glam up a little in a way that would have me pegged as going through a mid life crisis if I did it as a bloke: dye my hair and have it done in a nice style, get my nails manicured and painted, etc. If I was cute (and that would have to be one of the conditions to agreeing to the change) I'd try dressing provocatively to see what it's like to turn heads.
Of course I'd have to get laid too, to see what it's like from the woman's point of view.
