Final answer:
Connor Bradley likely worried about Dexter's conflicted emotions and dreams in relation to Judy Jones, whose behavior and disposition significantly affected Dexter.
Step-by-step explanation:
Connor Bradley's worries about Dexter likely stem from observations of Dexter's interactions and emotions regarding a character named Judy Jones. The various excerpts suggest that Dexter is deeply affected by Judy's behavior, her emotional state, and the changes in her life.
From her volatility during dinner that caused him uneasiness to her indifferent attitude towards his feelings and the impact of what he perceived as her insincerity, Dexter is troubled by Judy's influence on him and his inability to reconcile with his 'winter dreams', a metaphor for his aspirations and desires. Dexter's concern seems to be rooted in her capriciousness, which impacts him emotionally, as well as in the revelation that Judy may not be the ideal he had envisioned, as shown when Devlin comments on her faded beauty and Dexter feels a profound sense of loss.