So going back to the op...
bumping my fav thread :-)
One of my friend's friends saw me with her and was interested so he asked her for my number and we've been talking for a little bit now. But the two times he's seen me I've been sitting down, so he doesn't actually know how tall I am (I'm 99% sure I'm taller than him) and I've never brought it up 😬 should I tell him or should I keep it a surprise for when I see him again and I'm actually standing up
Obviously your height is something that bothers you a lot, so why not use it as an opportunity to confide in him? Something like "I have a confession to make - I'm the longest child" is gonna come across as really weird. Something more along the lines of "Hey can I tell you something? etc. etc. Being tall makes me feel etc. etc. and it sucks" would both clear any uncertainty that he doesn't like tall girls or something and be an opportunity to get closer to him. ;3
Or that's the way it works out in my head glgl