The advent of dating apps and online platforms for courtship in the 21st century has given rise to a unique lexicon for modern dating. Terms like “situationship,” “cushioning,” and “zombieing” reflect new dating dynamics and scenarios not experienced by previous generations. This paper analyzes survey data and trends surrounding seven common terms - situationships, cushioning, kittenfishing, zombieing, “date of view” experiences, “riz,” and stashing - used amongst Gen Z and Millennial daters. Situationships describe non-committed relationships existing between the casual and serious. Cushioning refers to keeping backup relationship options in case a primary partner does not work out. Kittenfishing entails intentionally using highly flattering profile photos or descriptions to appear more attractive to matches. Zombieing describes someone who cuts off contact unexpectedly only to resume communication later without explanation. A "date of view" is a date that resembles a business interview with rapid-fire questions rather than an organic chat. The phrase "riz" refers to easy charm or magnetism in attracting lovers. Finally, stashing refers to spending significant time with a clandestine companion who is kept apart from friends and family. Survey data indicates 62% of Gen Z feel disconnected from their parents due to differing generational understandings of such modern dating terminology. Further data reveals 75% of Millennials admit utilizing kittenfishing techniques on dating profiles. Qualitative research included one-on-one interviews with Gen Z and Millennials which suggest zombieing and situationships have become commonplace, representing larger cultural shifts like fear of commitment and keeping backup options. In conclusion, while technological innovations have greatly expanded romantic possibilities, they have also bred new complex relationship dynamics now encoded into dating terminology. Younger generations employ an extensive dating vocabulary reflecting new courtship norms, behaviors and uncertainties distinct from their parents’ experiences. This doubling of language underscores profound intergenerational disconnects. Bridging this widening vocabulary gap will be critical for improving cross-generational empathy and dialogue amidst rapidly evolving dating culture in the digital age.