You take your date with Wendy to a fancy kind of bar, where basically everyone was wearing clothing that looked much more adult, and sketchy than you thought would be. Of course your clothing was something to be desired as well. You were still wearing your every-day clothing, but felt out of place.
As for Wendy, she was wearing a fancy white overcoat, but didn't decide to remove it, and reveal what she was wearing underneath, because it matched some glittery red high-heeled boots that stopped at her knees which she was also wearing. However, what you found out about the bar is that it was karaoke night at the bar, which would cause some trouble for your date if you went up on stage. Despite being a good boyfriend, you couldn't sing at all, so you were worried about going on stage, and finding out how Wendy would react if you sang.