Except that he succeeds.

I gotta agree with OP here. He’s one of my favourite overhated characters. ‘Tis a shame many people dislike Zephyr, though justified..
 
Most Zephyr-haters say he’s just a lazy Casanova who doesn’t fit the Shy family. But having a phobia of failure isn’t laziness, it’s being paralysed into inaction while subconsciously undermining your efforts and self worth. Trust me, I know myself. And for that, he very well fits the Shy family. Though I  
wouldn’t argue with that last bit.

Someone with crippling self confidence issues that life seems to enjoy jerking around?
 
Yes, I can sadly relate.

honestly i can see how some people can relate, he a underachiever overshadow by his hero equestrian saving sister, as someone who brother always been the more successful one he is relatable, though personally i always saw him as the gay character who in the closet and hit on rainbow dash so no one find out he gay

Yeah, because I totally was forcing my crush on a lady who obviously rejected me… and also came up with some cringy pickup lines…

If I relate to him, then I want to knock the teeth out of my own head.

Yes, I too remember hounding disinterested women relentlessly despite their definitive rejections.
 
Oh wait, no I don’t.

True.

Basically me without the hot older sister.

God that episode was depressing