Craig attempts to "adult" by helping Naomie throw a fundraiser, but the differences in their planning styles threatens to expose the cracks in their relationship. Meanwhile, Kathryn takes steps to become more responsible, just as Thomas decides it's time to rekindle his friendship with Landon. Later, it seems that Cameran's matchmaking skills are finally paying off after Shep and Chelsea share a romantic evening together. But when Shep leaves town without making his intentions known, Austen swoops in to take his place.