My theme with my choices might seem odd by now. I'm pretty much choosing short and/or lesser known issues. This one starts with a Parker Christmas tradition May shares with her uncle: beating up a gang of criminals dressed as Santa. Spider-Girl #54
May thinks about plans for Christmas and wonders if other heroes celebrate the holidays. Her mother Mary Jane is pregnant with her second child which has been rather difficult on MJ. Peter naturally doesn't want to concern his daughter but nevertheless does consult an expert. After being shaken up by a run in with the Snake King she thinks of who she should talk with. Unfortunately May misreads how her crush/guy friend feels about her which is followed up after this issue. Throughout most of the series May has had some bad luck with guys. Apparently there was some concern from editors about her crush on a friend who was a few years older than her and legally an adult. This was the creative team dealing with the situation head on and while all we get is the impulsive kiss it does start an interesting plot. One that's dealt with maturely.
This isn't my favorite Spider-Girl issue or arc, I don't really care about the Serpent people she fights. Still that kiss does stand out though especially the stunned expression and the little Christmas tree in the background. I also fondly recall her trying to imagine--and failing--Darkdevil doing something holiday related. I liked the touch that she even considers the possibility of him being Jewish because she has no idea what he's like outside the mask.