I wonder if this makes sense, because if the man is a drunk or a mental patient, he is in even greater need. The man might resent you for not trusting him to spend the money properly. He knows that a lot of people think he uses the handouts to buy liquor, and if that is not the case for him, he may become indignant and refuse the opportunity to preserve what dignity he has left. The man might be so alienated from people that he can t take you up on your offer, for fear you will reject him at the last moment, adding devastation to his hunger. The man s appearance might be so shabby that he might not be able to enter the restaurant and buy food, so he may be very grateful for this extra help.
Homeless people are deficient in people skills, sometimes that is their only problem.
The man might have had so many bad experiences with rejection that he can t get up the courage to go in the restaurant without an escort. Recently during a severe winter in Washington, DC, a charity group tried to give blankets to street people. The street people were afraid of them and refused the blankets. Some of them froze to death. If a street person refuses something they desperately need, just set it down next to them and walk away.