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On this episode of That Stupid Dating Show, we unpack the chaos of situationships and the latest dating app trends. Is it love, lust, or just lazy texting? Tune in for laughs, cringe, and way too much oversharing.

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In this episode of That Stupid Dating Show, we welcome Jessica—sharp, hilarious, and proudly “terminally single.” She dishes on her one and only Tinder experience (spoiler: never again), what it's like navigating dating apps with zero patience, and why being alone is underrated. Plus, she shares wild stories from her time slinging drinks and dodging awkward pickup lines as a waitress and bartender. It’s part vent session, part comedy hour, and 100% relatable.

Grab a drink and buckle up—this one’s for anyone who’s ever ghosted someone mid-conversation or rolled their eyes at the phrase “just put yourself out there.”

Ever wondered what it’s like to date someone who talks about relationships for a living? Jeff didn’t—but here he is. This week, Michelle’s boyfriend joins the show to share his side of the story: the weird pressure of being “podcast material,”, and the reality of dating someone whose job is to dissect every red flag. Spoiler: It’s a chaotic mix of truth, laughter, and just enough tension to keep things interesting.

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On this heartfelt episode of That Stupid Dating Show, hosts Rane and Michelle meet Rob and Karissa—two resilient souls who’ve each weathered life’s harshest storms. From personal heartbreaks to major life setbacks, Rob and Karissa share raw, emotional stories of survival and strength. But in an unexpected twist of fate, those painful chapters led them to the greatest plot twist yet: each other. Watch as they recount the serendipitous moments, hilarious missteps, and tearjerking turns that brought them together in one unforgettable love story. It’s proof that sometimes, the stupidest show can lead to the most meaningful connections.