I guess the problem here is making your difficulty too low - by which I mean, possible. A few of those, fair enough, but you can really shoot yourself in the foot with it - natty 20s aren't magic; if there's no way the guy would have come to the mess hall because he's not stupid then no check needs to rolled nor risked to succeed and skip your entire adventure.

One of my chaotic players decided he thought he was evolving into a bird, and wanted to jump off a cliff. I warned him he would die, but he said "nah, he thinks he's going to grow wings when he needs them!" Persisted, so I let him jump off the cliff. "So what do I roll to see if I grow wings?" Nothing. You can't. You're not magic, and nobody in the party has any magic to help you. Did warn you several times and give you the opportunity to not. "But that's not fair, I wanted to roll it!"

You can roll for magical blowjobs and gold-farting goblins, but if they aren't going to happen, they're not going to happen.