It's about Kenny trying to pick up a mature, seasoned woman, but couldn't hack the competition, (OP)
Singed Eyebrows explaining how it is that he is able to keep up with his splitting (post 3),
Kenny listing his playlist for the romantic evening he has planned (post 4),
Dixie and Oldspark congratulating him on his evening and taste in women, respectively (post 5 & 6),
Kenny explaining just how old those grannies he was chasing were, based on the topic of conversation (7),
Mayhem is considering catching himself a granny, possibly marrying her, if Kenny's friend has a friend (8),
Papa Dave and I are, unsurprisingly, clueless (posts 1 & 9),
Dixie and Jackstraw took a stroll down memory lane (10 & 11),
and Kenny admitted that the evening didn't go as well as he'd hoped, as the competition was lively. (12)
Yes, there will be a pop quiz.