I think if he had started with more savings, he would have been less bitter about the failure. He still would have been able to take his girlfriend out for dinner.
This complaint made no sense to me. What was his girlfriend doing? Why does she rely on his largess to go out? Is she also a failed indiehacker, or was she using her own income to cover rent and all shared expenses? I think it's irresponsible to take a big risk with someone else's finances, and becoming bitter as you lose that gambit just makes you seem out of touch with reality.