“Age is just a number”… until you realize he’s still using his college meal plan while you’re shopping for a mortgage. 🥴
This week on Flirt. Fail. Repeat., we’re talking age-gap dating: power dynamics, cougar labels, and my own spectacular fails. Plus, Leo’s 25-year rule, Demi & Ashton drama, and why Priyanka & Nick are proof it can work.

“Age is just a number”… until you realize he’s still using his college meal plan while you’re shopping for a mortgage. 🥴 This week on Flirt. Fail. Repeat., we’re talking age-gap dating: power dynamics, cougar labels, and my own spectacular fails. Plus, Leo’s 25-year rule, Demi & Ashton drama, and why Priyanka & Nick are proof it can work.

“Age is just a number”… until you realize he’s still using his college meal plan while you’re shopping for a mortgage. 🥴
This week on Flirt. Fail. Repeat., we’re talking age-gap dating: power dynamics, cougar labels, and my own spectacular fails. Plus, Leo’s 25-year rule, Demi &amp; Ashton drama, and why Priyanka &amp; Nick are proof it can work.

The Age Gap Episode: Cougars & Cradle Robbers?

Flirt. Fail. Repeat. is the brutally honest dating podcast for anyone navigating love in midlife with a kid, a history, and a healthy sense of humor. Host Rachel is 40, newly back in the dating world after a 7-year hiatus, and quickly discovering that swiping right comes with more red flags than a parade. From awkward encounters to emotional curveballs, this is real-life dating with none of the filters—just one mom sharing her story, one spectacular fail at a time.

If you’ve ever juggled babysitters, bad dates, and late-night overthinking... you’re not alone. Pull up a chair, pour a drink, and get ready to flirt, fail, and laugh your way through it.

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Flirt. Fail. Repeat. is the brutally honest dating podcast for anyone navigating love in midlife with a kid, a history, and a healthy sense of humor. Host Rachel is 40, newly back in the dating world after a 7-year hiatus, and quickly discovering that swiping right comes with more red flags than a parade. From awkward encounters to emotional curveballs, this is real-life dating with none of the filters—just one mom sharing her story, one spectacular fail at a time. If you’ve ever juggled babysitters, bad dates, and late-night overthinking... you’re not alone. Pull up a chair, pour a drink, and get ready to flirt, fail, and laugh your way through it.

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The Age Gap Episode: Cougars & Cradle Robbers?

The Age Gap Episode: Cougars & Cradle Robbers?