If you walk the streets of downtown Portland, you will eventually come across this guy. He holds up his hand as if to give you a high five, that's his open every time to talk to you/ask for money.
If you haven't met him; sounds like a nice guy right? No. Do not engage this guy, he is a pos and a violent person/incredibly rude to homeless. He's a con man and does not need help.
It's okay to say "no" Portland. Don't be passive about driving and turning down asks for money, there are many who take advantage of that/are not in need of help.