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Prologue

NPR reporter David Kestenbaum tells host Ira Glass about the time, when he was doing graduate work in physics, he and his other single friends decided to figure out the mathematical probability that they'd find girlfriends. They wanted to know what the chances were that there was more than one person in the world for them.

Prologue

We hear a tape that a man named David Cossin made for a woman in Italy named Allesandra whom he'd met during a week he spent there, and with whom he'd fallen in love. He sent her a dozen tapes, including one where he tries to convince her to move to New York and be with him.

Prologue

Story of a romance that began in a mental hospital. Sometimes, the line between crazy and not crazy is blurry; certain behavior could mean either thing.

Prologue

Host Ira Glass talks to film critic Jonathan Rosenbaum of the Chicago Reader about an anonymous love letter that turned out to be very different than it seemed.

Prologue

Host Ira Glass talks to Chicago Tribune newspaper columnist Amy Dickinson ("Ask Amy"), the heir to Ann Landers, as she reads letters from those readers who don't yet know their love is doomed.

Act One: Prisoner Of Love

Shant Kenderian reads from his memoir 1001 Nights In the Iraqi Army: The True Story of a Chicago Student Held as a POW By the Americans During Desert Storm. During the first Persian Gulf war, Shant (reluctantly) fought for Saddam Hussein.

Prologue

When she began working as a temp secretary in San Francisco, learning the computers, wasting time, Andrea put together a graph with Microsoft Excel. Its title: My Love Life: A Ten Year Span. It made her feel good.

Act One: Corporate Culture

D. Travers Scott and his boyfriend spent six months gathering data on their own relationship and put together a report on it in the form of a corporate annual report.

Act One: Dr. Phil

In the wake of a break-up, writer Starlee Kine finds so much comfort in break-up songs that she decides to try and write one herself—even though she has no musical ability whatsoever. For some help, she goes to a rather surprising expert on the subject: Phil Collins.

Act Four: You Had Me at Hello

Comedian Jillian Welsh tells Diane Wu about one of the most romantic—and stressful—nights of her life, a night that paralleled the plot of a rom-com in several ways. A version of this story first appeared on the Risk! podcast.