Resolves positively if we survive the singularity and the regular person can just get 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.
1,000@DylanRichardson 1) If they're not sentient they are just a very sophisticated form of robot, that's cheap and easy enough that I almost certainly would guess yes. 2) Presumably it wouldn't be cruel, because they'd be purpose built to like the regular guy, even taking into account how the guy might change over time, e.g. via mental augmentation. 3) If it is possible to make life that feels significant anguish, then holy we are ultra fucked.