There is something oddly relatable about getting dating advice from a guy who hasn't opened a dating app in over two decades. Jay Schwedelson tackles two very different kinds of questions this episode - one sharp and practical about why your "great" offer is probably not great, and one completely unhinged series of dating questions submitted by listeners who really should know better than to ask him.

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Best Moments:

(01:45) Jay drops the cold truth: if you think your offer is great but results say otherwise, the offer just isn't great

(02:58) The 100% Rule - the single question you should always ask before trying to save a failing campaign

(04:18) Why throwing more money at a bad offer is a trap, and what to do instead

(06:15) Venmo requesting someone after a bad date - Jay's take is exactly what you'd expect

(07:45) Why going on vacation too early in a relationship is a recipe for disaster (he learned this the hard way)

(08:45) The real reason you need to Google someone before a first date, according to Netflix true crime

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Partner with Jay! https://www.jayschwedelson.com/contact

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Pre-order Jay Schwedelson’s new book, Stupider People Have Done It (out June 9, 2026). All net proceeds are donated to The V Foundation for Cancer Research—let’s kick cancer’s butt: https://www.amazon.com/Stupider-People-Have-Done-Marketing/dp/1637635206

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