I actually create caricatures for other people all the time. In fact, I've been doing quite a few for my colleagues and managers at work. Some are paying me if they want something specific, otherwise they've all been free gifts. I've also drawn plenty of myself, including my avatar here (which is a more basic silhouette). From what I've seen, everybody who has gotten one from me has been ecstatic about it. They love being immortalized in cartoon form, and they love the attention from the whole process.
Completely and utterly flattered. I love art, and I adore seeing other people's work. When someone gives me a piece of their art as a gift, I get red in the face and overwhelmed with happiness. And if it were a drawing of me??? God, the fact that I'd give someone the inspiration to draw??? Oh gee, I almost forgot, but I've gotten a drawing of me before from someone, actually. She drew both of us together as mermaids holding hands. It's hanging on my wall still. And even though I haven't seen her in a long time and our relationship (like, actual couple, not friendship. We dated for a short time) didn't work out, I still love the drawing.
If it came out of nowhere, it would surprise me, but I think I would be flattered and appreciate it very much, especially if it were competent. I can see how there may be a fine line between "creepy" and "flattering" when someone draws another person without their knowledge, but with the qualification of non-threatening admirer, I can't see how that would ever have bothered me. As it just so happens, there is a drawing of me that I was given by an artistic friend a few years ago, although I was informed of it ahead of time because I actually posed for it and it took a couple months for him to finish. I'm not sure entirely why he chose me as his subject, since he said he hadn't drawn anyone he knew before then, but it was an amazing gesture (to my knowledge he is completely straight and not an "admirer" in that sense). This is the drawing: It was a formidable effort on his part. It's fairly accurate too, not that that means anything, since I haven't yet shown a picture of myself here
Wow that looks really cool. I think I would like it. I only got one drawing from my sister. It's kinda old and outdated, but I still remember when she gave it to me, I was really happy. Doesn't matter if it's a drawing from a sibling/friend/classmate, I think I would act the same, as it clearly shows how the person cares about you/finds you interesting.
I'd think, "cool". My friends and I often draw pictures of each other; none of us are any good at art so it's all in jest. However, if someone gave me a serious drawing of myself I'd be flattered.
