Text-to-video retrieval enables users to find relevant video content using natural language queries, a task that has grown increasingly important with the rapid expansion of online video. Over the past six years, research has produced numerous methods, such as dual encoders, attention-driven models, and multimodal fusion approaches; however, fundamental questions remain about model behavior, dataset influence, and query difficulty. In this work, we evaluate 14 state-of-the-art retrieval methods across 3 widely used datasets under a unified preprocessing and evaluation framework. We analyze caption characteristics, including length, clarity, semantic category, and Action vs. Scene balance, and link these to model performance. Our results show that short, clear, and simple captions, such as those describing single actions or color attributes, achieve higher recall, while complex events, multi-step activities, or fine-grained scene descriptions remain challenging for all existing models. Attention-driven architectures better handle temporally dependent or multi-step queries, whereas dual-encoder and multimodal fusion models perform well primarily on simpler or single-category captions. Cross-dataset generalization improves with larger, more diverse caption sets, but generative captions do not consistently enhance retrieval accuracy. Overall, our findings highlight key dataset factors, benchmark challenges, and the interplay between query content and model architecture, providing guidance for developing more effective text-to-video retrieval systems.