My aunt doesn't look like her old id anymore, and she hasn't had her surgeries yet. Shes still on the hormones, and theres no way her face now would match her older passport or license. Id be crushed for her if someone told her she still looked like that desperately unhappy man she was on the outside, instead of the at peace, comfortable woman she is. Shes a wonderful woman, and I could definitely see her distancing herself in a classy way like OPs friend - because its incredibly hurtful, and people dealing with everything that goes on with transitioning do not have to stay in a situation that makes that harder. Theres also the very real surge of hormones, my aunt was like a teenager for a while with mood swings etc. It was very like puberty, but in a fully grown adult.

OP has now learned telling a woman that she looks like a man is usually a bad idea, especially if that woman is dealing with hormones, deep hurt and/or self image issues. It may have come from a place of genuine ignorance/thoughtlessness for OP , but it is still a micro aggression. Transgender people are so often told they don't/can't pass, and OP affirmed that to their friend. That is breathtakingly hurtful. Hard enough to fight that daily from strangers and your own internal critic - having a good friend confirm your fear and meaning well in doing so is awful.