@Ardashir  
Yeah, that’s usually either confidence or the ignoring of “leagues”.  
Chasing women, plural, that’s just playing the odds.

@Stotter  
It makes me wonder about some real-world guys I’ve known who kept chasing women ‘out of their league’; were they really that unrealistically self-confident, or did that just permit the illusion of a possible relationship while actually avoiding the real thing?

@Ardashir  
I put a lot of thought into headcanons.

@Stotter  
This argument makes a shocking amount of sense.

zephyr breeze: Dash…Youre preganaut…  
Rainbow dash: ah-ah…i…  
Fluttershy: GAH! Im s-so PEEVED right now!

It occurred to me just now, how his fear of failure kept him from progressing, but he doesn’t care about Rainbow’s rejection: Because pursuing her is the romantic equivalent of pursuing a job at this point.  
He knows he’s not going to start a relationship with her, just like he knew he wasn’t keeping a job. A break up would be a failure by another name, so he avoids that possibility by exclusively aiming way out of his league. I bet if she called his bluff, he’d have quickly found an excuse to avoid doing the work a stable relationship required and never make it to the second date.

“Get your stinkin’ hooves off of me, you damn dirty horse!”

He just sang this to her.
 
https://www.youtube.com/watch?v=eu196vZSe_I

@Kryptid  
Or he has yet discover himself of being gay.

@Background Pony #2C2A  
I think it would have given them plausible deniability: if people started complaining about him acting gay, Hasbro could always point to his behavior around Dash and say “See? Not gay!”

the funny thing, I expect this, before of the episode

I knew we’d be facing a lot more shipping content as a result of this episode; I just expected it to be FlutterDash instead of ZephyrDash.
 
@Kryptid  
While I don’t think that’s what they were aiming for, it wouldn’t exactly surprise me, either.

@Bexar Bandito  
Dash wins at faces in pretty much EVERY episode.

@Kryptid  
Or you’re thinking too much into this.

My theory is that the whole “Dash likes me” thing is just something Zephyr made up in an attempt to cover his gayness. Either that or Hasbro wanted to make him “gay” without actually making him gay.

dash wins at faces for the episode, hands down.

“There goes the last lingering threat of my heterosexuality.”

Know this a one sided ship right right now.  
Which make two so far on this show being cannon.

DELET THIS

And I thought her shippings with any of the bullies were weird. :/

@FSin  
I don’t think that’s the problem. Forget headcanon and let’s use logic! Rainbow won’t date this guy cause he’s a narcissistic prick. Yeah, that seems logical

@Mellow91  
Fluttershy’s parents sure seem to think otherwise. And they better stop thinking that. I’m not against her finding love, but this guy, he ain’t it.

@Prof.NightJack  
True. No matter what you think about Rainbow’s “barn door”, I’m sure she wouldn’t go for Zephyr in any case

@FSin  
But it swings both ways, just not for him.

@Mellow91  
Does not. Dangit.