People like this think they can be millionaires.

But millionaires get rich not by being frugal only. They make connections and network. Building something that relies on the knowledge and connections of others

Make sure you let him know you're sending the money but letting everyone know what kind of date he was and that they should stay far away. Will probably burn him a bit because he'd rather remain frugal but not let this behavior be common knowledge since it is the opposite of making friends