he's always been really squirrelly about what he does for a living and how he can afford what he affords. the truth is that he designed an app that became very popular and sold it but he never told anyone because he was awkwardly embarrassed about it. he had been working on this app since high school and never told anyone and then suddenly bam he had all this money and no reason to do anything. so i'd love if they dated for several years and he was weirdly evasive about how much money he had and how he made it and just said he did stock market stuff but eventually the lying and the covering up led to their downfall. which was the opposite of what he wanted he just wanted her to see him as he really was a weirdo nerd who liked to keep it simple.