Jake's back from Florida with a roulette win and some bachelor party receipts. Ilana has a major life announcement that's been months (or years) in the making.. Two listener questions: does astrology actually matter in dating, and how do you stop waiting for the other shoe to drop when something finally feels really good?

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Waiting for the Other Shoe to Drop & I Have a Big Announcement

Seeing Other People

Waiting for the Other Shoe to Drop & I Have a Big Announcement