Daniel Handler’s Essential Break-Up Playlist


Among his many talents, Daniel Handler is the master of painting the precocious youth in moments of existential peril — his alter ego is Lemony Snicket, after all, though we admit we like his lusciously written books for adults even better. In Handler’s newest novel Why We Broke Up , illustrated by the great Maira Kalman, teenagers Min and Ed have, well, just broken up. And now, “arty” girl Min is writing her basketball-playing ex a novel-length letter as to just exactly why, following the trail of their failed relationship’s trinkets and detritus — sugar bowls, ticket stubs — until she reaches the bitter end. The tale is as simple as it gets, but expertly rendered and, as far as we’re concerned completely true to the teenage experience.

We’ve all been through it, whether we’d like to admit it or not, so to ease the pain, we’ve asked Handler (who in addition to being a successful novelist just happens to be the sometime accordionist for the Magnetic Fields — who would have ever broken up with him?) to put together the ultimate playlist to help you get through any breakup, whether you’re sixteen or sixty. Click through to listen to Handler’s picks and let us know which tracks you count on to heal your own broken hearts in the comments.

The Magnetic Fields, “The Things We Did And Didn’t Do” Summary Of Song: I am pondering every detail of our broken relationship, including some details I made up. Sample Lyric: “All the things I knew I didn’t know and didn’t want to know, that you told me just to tell me later that you told me so, come flooding back to me now.” Further Context: 1/69th of the classic album 69 Love Songs, on which I play accordion. Suggested Use: Pondering ephemera from prior relationship, as in my novel Why We Broke Up, in stores now. Internal Monolog Whilst Listening: “It is necessary and therapeutic, not pathetic and obsessive, to fondle this movie stub.”

Roxy Music, “Over You” Summary Of Song: I wish I were completely uninterested in you and/or having sex with you right now. Sample Lyric: “Oh baby, this is nowhere.” Further Context: Bryan Ferry is Lord Byron with a martini in his hand. Discuss. Suggested Use: Considering booty call. Internal Monolog Whilst Listening: “But how I can get closure if we don’t go at it one more time?”

The Beatles, “I’m Looking Through You” Summary Of Song: I just realized you’re a terrible human being. Sample Lyric: “I thought I knew you. What did I know?” Further Context: This band has a few other good songs; you should totally check ’em out. Suggested Use: Remembering warning signs via 20/20 hindsight. Internal Monolog Whilst Listening: “And then there was that time she said she was at the gym but I know I heard ice clinking in a glass.”

Prince, “What’s My Name?” Summary Of Song: Get out, skank. Sample Lyric: “You never would have drank my coffee if I had never served you cream.” Further Context: My butcher is the president of the North American chapter of the Prince Fan Club. Suggested Use: Dumping prized possessions in dumpster. Internal Monolog Whilst Listening: “And stay out, you f*%&ing f*%&.”

Tom Waits, “Make It Rain” Summary Of Song: My love hurt me so bad I am resorting to primitivist rituals in a vain attempt to cleanse my soul. Sample Lyric: “What she done, you can’t give it a name.” Further Context: It sounds good when you’re pounding on the floor in time with the drums. Suggested Use: When utter desolation is giving way to apocalyptic fantasy. Internal Monolog Whilst Listening: “And the vultures will pick at his bones while his annoying, self-righteous mother rends her clothes in grief.”

The 6ths, “As You Turn To Go” Summary Of Song: I am attempting to direct your leaving me as I would a movie. Sample Lyric: “You know you’re the star of my life story, and I’m so sorry.” Further Context: The band chose the name because it’s impossible to say on the radio. Suggested Use: Crying in front of the mirror, you know, just to see what it looks like. Internal Monolog Whilst Listening: “I must have looked very photogenically unhappy in that train station.”

Yo La Tengo, “Damage” Summary Of Song: I ran into you at a bar and it was awkward. Sample Lyric: “I hope I mumbled goodbye as you walked out the door.” Further Context: Sung by people seemingly happily married. Suggested Use: Afraid to go to birthday party of common acquaintance. Internal Monolog Whilst Listening: “Out of all the gin joints in the world, blah blah blah.”

Emily Haines, “The Last Page” Summary Of Song: I’m trying to get over you, really. Sample Lyric: “By the way, it’s over without you. I’m in the way.” Further Context: Ms. Haines, the lead singer of Metric, is the daughter of renowned jazz poet Paul Haines. Nobody is excited about this but me. Suggested Use: Sudden attack of melancholy, too many months later. Internal Monolog Whilst Listening: “Maybe another bourbon will help me feel better.”

Dusty Springfield, “I’ve Been Wrong Before” Summary Of Song: You seem great, but I never pick a winner. Sample Lyric: “He used to smile at me and hold my hand like you do.” Further Context: Written by Randy Newman, who strikes me as a guy who’s been dumped a lot. Suggested Use: Prepping for date with rebound. Internal Monolog Whilst Listening: “I’m just going to say, ‘Oh, it didn’t work out,’ and nothing more.”

Stars, “Your Ex-Lover Is Dead” Summary Of Song: You know what? I am absolutely over you. Sample Lyric: “It’s nothing but time and a face that you lose. I chose to feel it and you couldn’t choose.” Further Context: Oh, don’t get me started. Suggested Use: Learning news of ex, not caring. Much. Internal Monolog Whilst Listening: “I hope they’re happy together. Kind of like I hope it works out with the Sunnis and the Shiites.”