alex is too much of a cynic to consider many of his recent memories positive. even the ones that were pleasant have later carried a negative sheen, but that was mostly his own fault for being a manipulative jerk. maybe some when he was younger. canon gives us a lot of shots of alex being happy as a little tyke. welcoming the gibborim to hell might at least be his most satisfying memory.

his worst? nico turning him down for being a jerk. also spending a year alone in hell.

his happiest in-game memories usually result from being drunk? there's a handwaved event that jill and i never got around to logging where he and allison just chilled on the roof of the mac with a bottle of wine after she graduated. he had a pretty decent time drunkenly hanging out with reilly during the beach party, as well. his worst was probably getting caught at the end of kidweek, and having to tip-toe afterwards since he knew rose could be watching at any time. it was easier after he realized she didn't really care, though.

he's got much worse ahead of him. at least he was able to keep the information contained that time.