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.

Writer Larry Doyle on a love that will not die, no matter how dead it is.

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.

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.

Aimee Bender reads her story "The Rememberer," about a woman whose lover is undergoing reverse evolution. One day he's a man, the next, a salamander.

We hear Billie Holliday, Keely Smith and Leo Reisman (with Anita Boyer) asking the musical question, "What Is This Thing Called Love?" And, reporter Sean Cole talks about love with Joe and Helen Garland, who fell in love during World War II, but married other people. Thirty years later they met again, felt the same love they felt when they were young, divorced their respective spouses, and finally married each other.

Susan Burton tells the story of how she used a clever scheme to get over a broken heart.

Host Ira Glass talks with producer Alex Blumberg about going on a date with a woman from Russia.

Jeffrey Brown wrote a comic novel called Clumsy, a beautiful and intimate account of his relationship with his ex-girlfriend. He talks with Ira about the relationship and why he chose to draw cartoons about it after it ended.

Host Ira Glass talks with Michael Beaumier, who runs the personals section of the Chicago Reader, and who functions as a kind of guardian angel for many of the singles who advertise in his paper.

Host Ira Glass explains how you can get away with anything if you claim you did it for love.

"Joyce, I don't need another Housekeeper." Producer Jonathan Goldstein talks with the man who placed this ad. Joyce is the woman who left him.

A story from David Sedaris about how the movie The End of the Affair almost ended his relationship. He argues that being in love sometimes means not saying what's going through your head.

Jonathan Goldstein and Heather O'Neill tell the true story of what happens when a person tries to intrude on a idyllic family of two, one of whom loves him, one of whom does not. For the first few years Jonathan knew Heather, her daughter Arizona was not very fond of him.

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.

Jonathan Goldstein with a story about what it's like to date Lois Lane when she's on the rebound from Superman. Jonathan Goldstein is the author of the novels Lenny Bruce is Dead and Ladies and Gentlemen, The Bible!.