I've always thought that Ash was suspiciously interested in Gary and suspiciously disinterested in girls. However, it's not just Gary: look at how he feels about Ritchie. He's awfully close to Brock too. And let's not forget "Ashley's" several crossdressing incidents. He doesn't really seem to mind them much. And that one time he actually kissed a girl (Melody) he didn't exactly enjoy it.
It's just extremely hard for me to believe the animators aren't hinting at something with all that.
Image evidence:
It's just extremely hard for me to believe the animators aren't hinting at something with all that.
Image evidence: