One well-studied solution to the need for vast amounts of human-labeled data is to use self-supervised training objectives in pretraining, which enables learning on completely unlabeled samples. Especially in the case of larger models such as LLMs, these pretraining procedures have demonstrated benefits [Devlin et al.,2018]. In this work we focus on training LLMs for producing semantically expressive sentence embeddings for User-Generated Content (UGC) in comment-style mediums. We provide a novel self-supervised training paradigm that leverages the structure of comment data and also demonstrate the efficacy of LLM generation for producing quality training data. Through empirical evaluation, we show improvements against existing baselines methods on several downstream tasks.