Oh my, that a big ask for her to get him to do it every year.My husband would, but not sure about every year.Havind said that, He and his mates don't mind dressing up as ladies!! Its not pretty,they are big guys with alot of facial hair ( ex football players, somewhat out of shape!!!)HA HA. As long as your friends enjoy it thats all that matters. And if he hates it he should stand up for himself a bit more.