There is so much projection and false assumptions in these posts. Not everyone has family to meet. I do not for one. Also, names are changed on birth certificates and can be changed on diplomas (at a cost); I do not know why someone would ask for a diploma however. Some people do not keep childhood photos.
The problem with these posts and Rebacca's is the projection of fears and psychological diplacement. The boyfriend does not deserve to know, and he may not find it shocking. You would. You are projecting your own feelings on Julie's love interest(s). And so was Rebecca. It would be nice for someone, once, to say something like: "if I were the lover, I would like to know" instead of telling us how to behave in relationships because of our trans past. Your posts seem transphobic to me.
Are you trans yourself? Do you know a lot of trans people? I know a trans woman who told her husband after ten years of marriage. He did not walk out on her. My girlfriend has never told any of her male lovers she was trans since SRS, and does not need to. What is your personal experience on this matter?
Dating is not easy for trans women whether they are attracted to men or women. Trans-trans couples are not rare for this reason, but telling or not, and how, belongs to the trans person.