He's pretty cucked. I've fairly well red pilled him at this point. My favorite question to ask these days is "are we better off than we were 30 years ago? 50 years ago? Are your parents better off than you?" It's too easy. The answer is almost always no and then yes. Especially when you ask if their mom was a stay at home mom. That is the demoralizing kicker.

No you aren't better off than your parents. They had 100% had it easier and their parents had it even easier.