Not enough stars

LettuceDragon: Hey there! Welcome to Wooden Workshop. I heard a bunch of other Points were forcing you through some challenge courses, so I decided to make my own! However, you'll need 10 stars before you can try it out. Come back when you've collected enough stars.

Enough stars

LettuceDragon: That's quite a few stars you've got! But I should warn you, my challenge course isn't going to be easy. Are you sure you're ready for it?

Yeah/Not really

Answering 'Yeah'

LettuceDragon: Alright, don't say I didn't warn you! Time to break out the big saws!

Answering 'Not really'

LettuceDragon: Dang... and I was getting excited about using some fancy new saws... well, there's always next time I guess.

Completing challenge

LettuceDragon: Even with all those extra saws, you still managed to complete it! You, my friend, are a force to be reckoned with.

Returning after winning

LettuceDragon: Hey, nice to see you here! Did you come here to try my challenge course again?

Yep/Nope

Answering 'Yep'

LettuceDragon: Awesome! Let's do this!

Answering 'Nope'

LettuceDragon: Hey, that's fine. Just swing on by anytime you want.