"name five of their songs" questions person A's (the one wearing the band t-shirt) knowledge of the band.
"name five women who trust you" questions person B's (the one who asked the 1st question) relationships with women in their life.
therefore "name five women who trust you" is much more loaded than "name five of their songs", making it a response that is, perhaps, too rude and unnecessary. although, assuming person B asked person A to name the songs unprompted (this is probably what usually happens), this could be an appropriate counter-question as sometimes a ruder response is necessary when dealing with annoying people.