Yes it's infuriating to see someone you care about fall for an obvious scam, yet... I don't know... If it's his money and it makes him happy, or a little less sad, a little less lonely... Why not...
Honestly the main problem is one of efficiency not whether buying happiness with money is a bad idea. Being less sad is more important than having money, but you do need to plan ahead so you don't run out too quickly.
If this sounds surprising to you then probably you have enough money that you don’t need to give all of it away to be less sad.
We don't need voter id or age verification laws, we need laws that make any form of deliberate online deception for profit a crime punishable by jail time.