HELLO ^ i can absolutely volunteer him as tribute for a slightly less creepy version of this where he absolutely does draw her and also absolutely internalizes it LMAO so he wouldn't send them to her, at the very least maybe he posted something in the past that had a piece of her tattoo or part of her face but it would've been a long while ago so she may not have even seen it (til she did) i also have a funny kind of platonic idea for her escort days but could very well provide awkwardness on their end anyway??