Most Helpful Guy
No it would not look bad, but try to help him get a job asap. Even if its a favor that if he tries to refuse. Just point out it looks bad on you that he isn't able to look out for himself. And he will accept the help XD.
Most Helpful Girl
Its your birthday girl, do what makes you happy! if you want you can give him the money so he can pay for it so it doesn't look like you are paying?