Considering him, and Dinky are close in age, I wouldn’t mind that honestly. (Though, I’m not much of a ‘shipper, I don’t care either way.) I don’t think he has much of a chance with an immortal princess like Luna though.
 
I also wanna add, I love the cartoony zip lines in the second panel. You don’t see those often in still image comics.  
They’re also quite common in the show, (and in most American cartoons for that matter, I even saw them in an early episode of the Simpsons) so it kinda helps it keep in style with the show.

As will mine.

Pipsqueak got shot down by Luna in >>18726.  
If this tumblr heads in a DinkySqueak direction, my jimmies will be rustled.