I will be funny when he gets audited by the IRS.
That might make him put the crack pipe down for a little bit.
Any future girlfriends are put on notice that he will expect his date to pay for his meal too.
The money is given to him as gifts. He doesn’t owe taxes on any of it.
If a person gives him more than $12,000, the sender must pay a gift tax to the IRS. That’s the only tax angle to this story.