I'm talking about the episode "The Hobbit" where Lisa asked Leopold out on a date on Wendy's suggestion . I was always baffled as to why Wendy thought asking somebody out is a good way to boost somebody's confidence level , for me personally that's a pretty good way to get kicked in the balls , metaphorically speaking .
But I realize now that Wendy thought Leopold would have the decency to go out on said date so Lisa could have a better self image . Leopold didn't have to be romantically involved with Lisa , he could have just hung out with her every once in a while .
Maybe I'm glamourizing and moralizing "Pity Dates" , maybe that opinion is wrong , it's just that , we should all help one another build up our confidence levels , self esteem and self image however we can .