Oh makeup. I was a wreck early in my transition. My wife helped me pick out some makeup and taught me some basics. She then tolerated my inevitable crying and delays each morning when I would make a mistake and feel like I had to start over. Between trying to learn everything and going through Puberty 2 : Estrogenic Boogaloo, it was kind of rough.
Pretty great on the other side though. Few things have felt as good as my wife asking me for makeup tips!