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 Bring It On as they also share stories about the early 2000s, siblings that have a little too much chemistry, and TWINS (are they creepy or totally normal and not weird at all??). Will Torrance and Cliff spend the rest of their lives together?
Checkout previous When Harry Dumped Sally w/ Tess Menzies & Natasha Vinik HERE
