This can be seen as "money can buy happiness part 2"! A few weeks ago I met up with a group of friends for drinks and had a civvie date with me. We ended up eating dinner nearby.
As my date and I were getting to my car we approached by a homeless person that appeared to be a trans guy. I'm not 100% sure but I'll use male pronouns. He told me he was homeless and hungry and did not seem drunk or high. We talked for a short while and I asked whether there was a shelter nearby he could use. Said he was going there but wanted some food first. I considered giving him my leftovers but worried that would come across as gross, so I gave him a $5. He was very grateful! :)
Then I thought about things. Between drinks and then dinner I probably spent $50 or so. That was nothing, just a night out! And here was a guy that genuinely seems grateful for $5. It made me feel guilty. He probably also needed more human contact and I felt I should have talked longer. I know that giving to charity is more effective than giving it individuals and I do that, but I still felt afterward I should have done more!
What would you have done?

