Scott tells the increasingly bizarre true story of Darren Sherman, a management consultant who wouldn’t let a failed first date go—pursuing a woman for $50 with emails, voicemails, threats of legal action, and even calling her employer.
Scott presents what he describes as “the weird and wonderful story of Darren Sherman,” a tale circulating online about online dating gone wrong. Darren met Joanne at China Grill, a posh New York restaurant, and paid for the meal when she offered to split it. When Joanne didn’t call back, Darren emailed asking for $50 for her portion of the dinner. She didn’t respond, so he escalated: a voicemail with the refrain “do the right thing,” repeated emails asking her to acknowledge receipt, and threats to issue a summons and contact her employer.
As Joanne ignored him, Darren’s persistence became increasingly absurd. He emailed her his credit card bill with “do the right thing” written across it, called threatening to contact her employer and take her to court, and eventually phoned the restaurant’s general manager to try to settle the matter through them. The restaurant staff, unsurprised, told Joanne not to worry and offered her a free drink instead.
Scott and the team debate the ethics: Laura thinks it’s outrageous, while others argue Joanne was rude not to call, and point out that Darren actually left a $20 tip, so he was only requesting $50 of a $107.83 bill—meaning she benefited from his generosity. A caller then shares her own similar experience: she was texted a £35 dinner bill after a date didn’t work out, and she sent back half (£17.50), which she now regrets. Another caller describes a blind date where his cousin’s date made an elaborate gesture suggesting he pay for the whole meal, and they split it anyway.
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