Navigating Financial Expectations in Relationships

From fro-yo runs in his parents’ Neil Sedaka-signed red Jaguar to unexpected parking lot meet-cutes, Jared is enjoying his Del Ray Summer. A listener shares a quirky first-date story where everyone says her date looks like Lil Dicky, and he eventually snaps! Jared and Jordana debate whether his reaction was fair or a red flag. They also tackle tricky dating dilemmas: when it’s fair to ask for a breakup refund after a partner cheats, how to date confidently with an invisible disability, and whether frugal habits in love are charming or a hard pass. Plus, they unpack a first date with an eight-year sex hiatus, weighing the context and what questions matter before moving forward.

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