You know what? I think there could be potential for a really good series or parody on the "hit on waiting girl" trope.
Like for example, there is one romcon series where the MC gains telepathy, but if he is confessed to he will die, due to some shrine curse. Thus he actively has to try to sabotage confessions by his friends that are interested in him.
A similar plot device could be used for this proposed series where someone is cursed with something dire, and has to get in a serious relationship with a complete stranger to escape. Add some limitations like limited amount of interaction time, which makes the hitting on girl the only real option, and you got a series. Go serious, silly, informative(actually show how to treat and hit on women respectfully, how to understand when/where it's appropriate), romantic, any or all the above.
Or it could go the opposite route, where hitting on girls gives points or progress or power up towards some goal.
It could even be a sort of parody training arc, where the mc has to pick up a celebrity or 0.000001% chance of success, and thus stuck hitting on strangers
Or a romantic groundhog day sort of loop where a guy has to successfully hit on a specific girl and start a relationship to escape. Thus would be forced to try all sorts of pickup methods and fail, and gradually learn more about the person and in time would actually grow to genuinely love/want the relationship.
Just spitballing ideas, but I think there is serious potential for a series in this vein.