Since you will be Red and you have trainers from later games you could play with the idea of how Red will and always be cooler than any other trainer ever. I can come up with two ideas, your friend running into Red and freaking out because they ran into the awesome Red. Or having Red being a jerk claiming that no is as cool as him
Stuff I hope to do by the end of the year:
Prism - Original design: Done except for the bow
Akihito Kanbara (Idol) - Kyoukai no Kanata: Need to add details
Drag Cloud - Final Fantasy 7: Need dress, wig and braids
Princess Daisy - Mario: Haven't even started
Bahamut - Final Fantasy 4: I need wig, and to make the wings
The Best Costume Ever - It's a surprise: All I need is the wig!