I think the best way to cash in on the fun side of the fun/status tradeoff is probably mostly rooted in adopting a disposition and outlook that allows you to. I think most people self limit themselves like crazy to promote a certain image and that if you're really trying to extract fun-bang for your status-buck, then dissolving some of that social conditioning and learning to be silly is a good way to go. Basically, I think there's a lot of fun to be had for those who are comfortable acting silly or playful or unconventional. If you can unlock some of that as your default disposition, or even just a mode you can switch into, then I think practically any given activity will be marginally more fun.
I think that most people have a capacity to be silly/playful in a way that is really fun, but that they stifle it mostly for social reasons and over time this just becomes a habitual part of how they interact with the world. I don't expect this point to be controversial.
One of the main social functions of things like alcohol and parties seem to be to give people a clear social license to act silly, playful, and even ~outrageous without being judged harshly. I think that if one is able to overcome some of the latent self-protective psychological constraints that most people develop and gain a degree of genuine emotional indifference towards status, then they can experience much more playfulness and joy than most people normally permit themselves.
I know this isn't really a self contained "Friday night activity" in itself, but I think that general mindset shifts are probably the way to go if you're not terribly status-concerned and looking for ways to collect fun-rent on it. I think there's a lot to be said for just granting yourself the permission to be silly and have fun in general.
Thank you for making this gradient way more legible! (Just fyi, I upvoted your comment).
I disagree that {becoming religious, child number/earliness} are against the spirit of the question. I believe that extracting as much information as possible can be done non-rudely, asking out people is rude. Not sure whether rudeness is immoral.
Agree on the illegality, although that really depends on the country/type of sex work.