# Evaluating Language Models in Realistic Conversational Contexts

arXiv: https://arxiv.org/abs/2608.26131 · HTML: https://mlsanity.com/paper/2608.26131/

## Key facts

- No citing papers in the map yet (data through 14 Oct 2026).
- Builds on 37 of its 45 references that are in the map.
- First posted on arXiv 24 Jun 2026.

## Builds on (most cited first, 30 of 37)

- [The Llama 3 Herd of Models](https://mlsanity.com/paper/2407.21783/) (2024)
- [Sentence-BERT: Sentence Embeddings using Siamese BERT-Networks](https://mlsanity.com/paper/1908.10084/) (2019)
- [BERTScore: Evaluating Text Generation with BERT](https://mlsanity.com/paper/1904.09675/) (2019)
- [Measuring Mathematical Problem Solving With the MATH Dataset](https://mlsanity.com/paper/2103.03874/) (2021)
- [GPQA: A Graduate-Level Google-Proof Q&A Benchmark](https://mlsanity.com/paper/2311.12022/) (2023)
- [G-Eval: NLG Evaluation using GPT-4 with Better Human Alignment](https://mlsanity.com/paper/2303.16634/) (2023)
- [Beyond the Imitation Game: Quantifying and extrapolating the capabilities of language models](https://mlsanity.com/paper/2206.04615/) (2022)
- [MMLU-Pro: A More Robust and Challenging Multi-Task Language Understanding Benchmark](https://mlsanity.com/paper/2406.01574/) (2024)
- [Instruction-Following Evaluation for Large Language Models](https://mlsanity.com/paper/2311.07911/) (2023)
- [Chatbot Arena: An Open Platform for Evaluating LLMs by Human Preference](https://mlsanity.com/paper/2403.04132/) (2024)
- [Evaluating Very Long-Term Conversational Memory of LLM Agents](https://mlsanity.com/paper/2402.17753/) (2024)
- [Personalizing Dialogue Agents: I have a dog, do you have pets too?](https://mlsanity.com/paper/1801.07243/) (2018)
- [AlpacaFarm: A Simulation Framework for Methods that Learn from Human Feedback](https://mlsanity.com/paper/2305.14387/) (2023)
- [ChatEval: Towards Better LLM-based Evaluators through Multi-Agent Debate](https://mlsanity.com/paper/2308.07201/) (2023)
- [DailyDialog: A Manually Labelled Multi-turn Dialogue Dataset](https://mlsanity.com/paper/1710.03957/) (2017)
- [GSM-Symbolic: Understanding the Limitations of Mathematical Reasoning in Large Language Models](https://mlsanity.com/paper/2410.05229/) (2024)
- [Wizard of Wikipedia: Knowledge-Powered Conversational agents](https://mlsanity.com/paper/1811.01241/) (2018)
- [MT-Bench-101: A Fine-Grained Benchmark for Evaluating Large Language Models in Multi-Turn Dialogues](https://mlsanity.com/paper/2402.14762/) (2024)
- [LLMs instead of Human Judges? A Large Scale Empirical Study across 20 NLP Evaluation Tasks](https://mlsanity.com/paper/2406.18403/) (2024)
- [MuSR: Testing the Limits of Chain-of-thought with Multistep Soft Reasoning](https://mlsanity.com/paper/2310.16049/) (2023)
- [MultiChallenge: A Realistic Multi-Turn Conversation Evaluation Benchmark Challenging to Frontier LLMs](https://mlsanity.com/paper/2501.17399/) (2025)
- [The Ubuntu Dialogue Corpus: A Large Dataset for Research in Unstructured Multi-Turn Dialogue Systems](https://mlsanity.com/paper/1506.08909/) (2015)
- [Evaluating Correctness and Faithfulness of Instruction-Following Models for Question Answering](https://mlsanity.com/paper/2307.16877/) (2023)
- [Can You Put it All Together: Evaluating Conversational Agents' Ability to Blend Skills](https://mlsanity.com/paper/2004.08449/) (2020)
- [MuTual: A Dataset for Multi-Turn Dialogue Reasoning](https://mlsanity.com/paper/2004.04494/) (2020)
- [Long Time No See! Open-Domain Conversation with Long-Term Persona Memory](https://mlsanity.com/paper/2203.05797/) (2022)
- [Topical-Chat: Towards Knowledge-Grounded Open-Domain Conversations](https://mlsanity.com/paper/2308.11995/) (2023)
- [MT-Eval: A Multi-Turn Capabilities Evaluation Benchmark for Large Language Models](https://mlsanity.com/paper/2401.16745/) (2024)
- [Open-LLM-Leaderboard: From Multi-choice to Open-style Questions for LLMs Evaluation, Benchmark, and Arena](https://mlsanity.com/paper/2406.07545/) (2024)
- [No Free Labels: Limitations of LLM-as-a-Judge Without Human Grounding](https://mlsanity.com/paper/2503.05061/) (2025)

## Abstract (arXiv)

As Large Language Models (LLMs) are increasingly deployed to serve open-ended, multi-turn interactions, evaluating conversational quality at human scale has become a central challenge. Existing evaluation frameworks built for summarization, translation, or short-form QA tasks fall short of adequately measuring the consistency of human-scale dialogue, especially when derivation and validation of these metrics themselves often rely on synthetic rather than human sources. We fill the gap by introducing UPHELD (UPwork Human-Scale Evaluated Long Dialogues), a large, reference-full benchmark for evaluating human-scale conversational ability beyond factual correctness. UPHELD consists of hundreds of complete human-to-human dialogues authored by professional script writers, with realistic turn densities and 36,000+ per-turn human annotations across 30,000+ expert-generated dialogue turns. Using UPHELD, we systematically evaluate classical automatic metrics and reference-free LLM-as-a-judge approaches, and find them unreliable when correlated with expert human judgment. Building off this analysis, we use UPHELD to develop a Mixture-of-Judges framework that combines multiple evaluative signals and improves correlation with human assessments by approximately 30%. Overall, UPHELD provides a robust, human-grounded foundation for evaluating human-scale conversational intelligence that fills a crucial gap in the pre-existing LLM dataset landscape.