If someone I know well puts up a journal that says 'taking requests' I might, but even then its rare that I do. Unless its some godlike artist thats impossible to copy or someone I highly admire, I'd rather just draw it myself :'D
Personally, I think the only time one should ask for a "gift" or rather, request something is if the artist has openly stated that they are doing requests. Otherwise, if you want something, you should at least have the courtesy to offer a trade or commission.
"Do you think you can do this? I'd be happy to offer this in return!"
I find it insulting to just ask for a free gift out of the blue like that; I mean, you WANT this, but if you want it free, it's like saying it's not worth anything and should be free. Hmm..
Voted Sometimes. See, I'm one of those people who give out gifts a lot, not expecting anything in return. I give out gifts a lot on Gaia and I often buy my buddy things she is saving up for. She is one of those people who feels guilty for not giving a gift in return. She feels she owes me for all that I have gave her. I really couldnt care if she gave me anything back,and slendom have anything in particular that I actually want to recieve. Not to big on random gifts to me because of the "Oh thankyou! You shouldnt have!"*thinks the gift is the most horrible thing ever but is too nice to say anything* factor.
So I compromised by telling her what she could get me in return, and call it a gift and therefore even. (mostly "Post in the Roleplay" type stuff. Anything to make her feel not guilty)