If you want to listen to something while browsing OkCupid, this This American Life episode is something I would recommend.
I amplify and explore peculiarities. My usual inclination is to take the absurdity in my current situation and calculatedly compound on it, managing to always stay within bounds of protocol. It is not by conscious direction, and it has two sides.
As far as fun goes, this is a huge plus.
Oh, it's a famous mathematician's birthday? We should totally bake him a cake with his epitaph, and make a piñata out the German secret code machine he cracked so we can "take a swing" at "cracking" it too.
Breaking Bad party? Blue meth jello. Indisputably.
Drawing a squid? It only makes sense if it inks itself.
Made s'mores in the fireplace? We should probably read about the history of s'mores. The next logical step is to taste test all published s'more varieties, appraising and criticizing each for their merits and demerits, charting them - and then it will be clear how to invent the best variety (graham with banana wedges and cocoa-coconut-brownie. ;])
Another advantage of this inclination is that this gets me into a lot of ridiculously fun eccentric hobbies like organizing and participating in competitive puzzle solving events, grappling tournaments and indoor aquaponic gardening.
A disadvantage, although they always end up being things to laugh about, is that I'm prone to misadventure - I once camped in a rainforest unprepared for it to rain. I get along with people who find thrill and fun in misadventure.