When Harry Dumped Sally is a sharp, hilarious relationship/romantic comedy podcast hosted by comedians Tess Menzies and Natasha Vinik, where modern dating disasters are dissected with brutal honesty, dark humor, and zero romantic delusion.
Each episode, Tess and Natasha dive into real-life breakups, bad relationships, situationships, and emotional train wrecks—either from their own lives or submitted by listeners—and analyze what actually went wrong. From ghosting and gaslighting to love bombing, cheating, and “we were never exclusive” excuses, no red flag is too small and no story is too messy.
Blending stand-up sensibilities with therapy-session vulnerability, the hosts break down the psychology behind failed relationships while roasting the absurd behavior that keeps people stuck in the same toxic cycles. Along the way, they offer comedic advice, hot takes, and the kind of clarity you usually only get three months after the breakup.
This week, Natasha and Tess share a night filled with laughs as they discuss the iconic romantic comedy Fire Island as they also share stories about two relationships in this modern take on Pride and Prejudice! We talk about whether or not recycling is real, the best part of the ice cream cone, and getting lyme disease despite being an indoor girly. How long will sweet Howie and dumb Charlie stay together? Can prideful Will and prejudiced Noah last forever?
Checkout previous When Harry Dumped Sally w/ Tess Menzies & Natasha Vinik HERE
