Does Reasoning Improve Psychological Depth in Large Language Models? It Depends on Who's Judging

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LLM-as-a-Judge evaluators are increasingly used to score open-ended generation, yet a judge's correlation with human ratings on its development set may not guarantee valid measurement when outputs are closely matched and human preferences are subjective. We study this failure mode through psychological depth in short stories. Seven human readers and an LLM-judge ensemble selected on the original scalar Psychological Depth Scale dataset ($ρ= 0.646$) evaluated 60 blinded, prompt-matched story pairs from GPT-5 vs.\ GPT-4o and DeepSeek-R1 vs.\ DeepSeek-V3. Human preferences showed no universal reasoning advantage: GPT-5 was modestly preferred over GPT-4o (60.0--62.9\%), whereas DeepSeek-R1 trailed V3 (42.9\%), and inter-reader agreement was near chance (Krippendorff's $α= 0.070$), with within-reader consistency and recurring weighting patterns suggesting structured heterogeneity rather than random responding. The judge, by contrast, favored reasoning outputs in 89.0\% of dimension-level comparisons and 59 of 60 pairs on aggregate PDS, uniformly across all five evaluator configurations, and its scores were associated with surface features such as sentence length and lexical diversity. These results suggest that development-set performance is insufficient evidence for deployment validity on a shifted distribution, and that point-estimate judges can obscure the heterogeneity in subjective human evaluation.