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Since the Beginning  -

@Background Pony #CADA
 
True. I don’t know if it’s poor execution as much as it isn’t great execution. They already had a fixed scenario with a fixed character, so it didn’t leave much room to be creative. If you change the template, then you ruin the point of the DLT comic. If you alter the character too much, then they’re out of character.
 
There was a way to make it more entertaining, but I couldn’t tell you what it was. This just had no choice but to get awkward, because this sort of interaction probably ends at panel 2 or 3 (4 if you don’t understand social cues) if not forced.
Background Pony #4D61
@Background Pony #CADA
 
The execution is fine, though. The term ‘waifu’ nowadays has been so thoroughly diluted that it could pretty much be used to refer to any female character that someone admires/feels affection for in nearly any context. Besides, maybe the human knows her, even if she doesn’t know him? Perhaps he’s a fan, or a secret admirer… or a stalker…
 
… aaand here’s your joke rationalization, with a side of fridge horror.
KennyC
Nightmare in the Moon - Had their OC in the 2024 Derpibooru Collab.
Lunar Supporter - Helped forge New Lunar Republic's freedom in the face of the Solar Empire's oppressive tyrannical regime (April Fools 2023).
Crystal Roseluck - Had their OC in the 2023 Derpibooru Collab.

Wow a pony that don’t like when there being treated nicely?(I can only wonder what the doing hurtful things one would have been like)but I like the look of this pony :D
Background Pony #9432
@Dogman15  
And that matters why? It could have been Tiarawhy, ColdBloodedTwilight, anyone else. Bad execution is bad execution.