Resolves positively if we survive the singularity and the regular person can just get a 3+ sentient catgirls that really like him romantically without any self improvement or effort longer than a day on the guy's part. If the AI can't do it instantly, it should at least be able to do so within a century while keeping most of the Pre-Singularity population alive meanwhile. If no singularity, resolves N/A in 2036.