So I've known this guy, he works for a client of ours but I haven't met him in 2 years, tho we talk on the phone fairly regularly. I used to see him 2 3 times a week 2-3 years ago but not since then and I managed to run into him on the street. He easily wouldn't have recognized me and I should have just kept walking looking the other way but I couldn't resist and I stopped him. Well he did not recognize me until I said my name and even then he didn't seem to click easy (my male name is very unique and doubt he knows another powers with that name)
Then with an expression of shock he said, OMG WTH I didn't recognize you. You look..... SOOOO completely different. I just said, yeah that the new me. (Didn't want to say that's 45 lbs and HRT ) We both had to run but said we would catch up. Now I wonder whether he put it together or wrote  it down to weight loss. I kinda hope he will txt me or email to find out more but unlikely because I could tell he felt uncomfortable and was happy to leave.

This me about a year ago and that day sans makeup in boy mode


I feel like I should have just told him but running into him a very big surprise for me too and I still feel like I need to plan how to do it.

It's unlikely he figured it out, for most people it's the least likely scenario they might consider (unless you have some notable breast development). But you're right that our changes can be quite noticeable and even a bit disconcerting to people who haven't seen us for a while.