Thomas looks a bit upset but Dracula says this due to Thomas giving up and feeling down on himself, of course, Thomas is upset at this and asked if Dracula went through this.
 
( he knows Dracula’s history but wonders if Dracula ever felt like giving up which he did want to during his younger years, perhaps Dracula did not say the exact words like give up but just felt defeated and did not want to fight anymore when he was young when he was telling his story because it does not have to be word for word just the basic idea of feeling defeated so it still makes sense)
 
Dracula gives him a pep talk about he can be a strong wolfpony but he has to prove himself he is not soft but a fears wolf who can handle things on his own and can fight if he needed too
 
Dracula boosted Thomas’s confidence so he can be brave and help him but is also an “eh why not” Erik was happy with Dracula and Dracula was happy and Thomas got to eat and all was good
 
part 32: https://www.deviantart.com/mr100dragon100/art/A-King-s-Journey-Home-Part-32-888124427  
part 34:
 
also yes those 3 ponies in the 3 third (?) are characters from the original Dracula