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.

A guy in Key West makes a series of grand gestures, each one more outrageous than the last. He goes so far that we need to say that this story, from Miki Meek, is not for kids.

An act named after two TV shows, one where women sit around and talk, the other where men sit around and talk. If men are from Mars and women are from Venus, when you switch from one planet to another, what do you need to know about love? We hear from several transsexual men who've done exactly that.

How much can you trust whether somebody who you think is close to you really is close to you? Saidu Tejan-Thomas Jr.’s been thinking about that question since a recent visit with some of his childhood friends in Sierra Leone. (37 minutes)

Pete found a bag of maybe a hundred letters in a dumpster and found himself completely wrapped up in the lives of the two people in the letters.

When adults talk babytalk to each other, it is precisely to avoid having real conversations and experiencing real moments with each other. People almost never discuss babytalk in public. This American Life producer Nancy Updike and her boyfriend—Chicago journalist Adam Davidson—agreed to step forward and speak the truth on the subject.

From England, Ruby Wright has a story of an affair where—even years after it ended—it wasn't much discussed. Ruby Wright's radio show Ruby's Chicky Boil-Ups airs every other Sunday on Radionowhere.

Chicago writer/musician Rennie Sparks, a member of the independent band The Handsome Family, reads "Skanks," a story of a girl struggling in a situation where some rules are strict, but other rules are up for grabs.

Brett Leveridge reads from his column for Might magazine, which he turned into the book Men My Mother Dated and Other Mostly True Tales.

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.

When Anne Staggs started to fall for an inmate named Charles in the Texas prison system, she was up against odds as daunting as they ever get for two people. It was against the rules, possibly dangerous, and could have gotten her fired.

A live performance detailing a humiliating love affair. When comedian Mike Birbiglia was in high school, he fell for a cool girl named Amanda.

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.

Miriam and her husband were development workers in Afghanistan. They'd had a whirlwind romance themselves, so when they heard that their driver was in love, but didn't have enough money to propose to the girl, they made a grand romantic gesture: They gave him $10,000 to pay for the dowry and the wedding.

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.

Bill Bradley press secretary Julia Rothwax explains how a political crush works. This is a crush that wants only for a candidate to get elected to office.

Joel and Kate were both working in a psychiatric hospital in Belmont, Massachusetts. They both like each other, and she tries to impress him by always wearing her favorite pair of jeans.

Viola disguises herself as a man, takes a job working for this guy with whom she promptly falls in love. He believes the pretense: He thinks Viola is a man, so he never gives her a second look.

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.

Writer and nationally syndicated sex columnist Dan Savage explains what actually happens in non-monogamous couples, how they make it work, and whether they're happy.

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.

Amy Bloom tells the story of her husband, Brian, getting Alzheimer's and wanting assisted suicide. Her search to find a way to do that led her to Dignitas, in Switzerland.

Elna Baker interviews comedian Michelle Buteau about one of her first big romantic challenges.