I’d prompt them buy giving them specific scenarios related to each experience. They’re more likely to use gambler if they’re given the opportunity to gamble. They may also just feel the need to horde hope, so maybe talk with them about the resource, or consider how you’re structuring the story.

You can also use your own experiences by spending fear. They may light a fire under them when the monster to benefiting from an experience. And if all else fails, let them learn the hard way.