My roommate had the hardest time with it for 2 reasons- first, she's known me for 12 years and second, she really did not want to give up her "male" friend. Since I first told her my new name months ago she always uses it, but she still sometimes slips with the pronouns. She corrects it right away, but when it's in front of others, especially strangers, once the "he, his, him" is out then the damage is done. For a while, she just took to using my name every time in place of using pronouns, specifically so she wouldn't slip up. I don't give her a hard time about it because I know she's trying. But like Jay and others said, for those that have known us for a while it can be difficult.