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Step 1
Open with something sweet. It’s hard to recommend something specific here. Everyone has their own songs for this occasion. You know what will work and what won’t for this occasion, and it should be personal.
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Step 2
Consider this scene from "High Fidelity": “Do you have soul?” a customer asks John Cusack, who responds after a brooding pause, “That all depends.” It’s time to get soulful. Look to titans like Al Green, and especially Mr. Pitiful himself, Otis Redding. You can’t go wrong with “I’ve Been Loving You Too Long (To Stop Now)” or “Pain in My Heart.”
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Step 3
Play it by ear, but make sure to let that special someone know the heartbreak hasn’t affected your impeccable taste. If you’re carrying a torch for a country fan, try some Hank Williams. More on the alt side of the country? How about the Cowboy Junkies' cover of Hank’s “I’m So Lonesome I Could Cry.” For an of-the-moment flavor, why not check out “Someone Great” by LCD Soundsystem, as moving and human a synthetic ballad as you’re likely to find.
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Step 4
Try Cat Power for heavy emotional artillery. You don’t have to be nursing a broken heart to feel Chan Marshall’s voice cut through you and raise the hair on your arms . . . but it helps. Moping around in that Pixies t-shirt she gave you? Use “Hey.” As long as you’re bringing out the big guns, try “The Beautiful Ones” by Prince, a less-famous gem from "Purple Rain." It’s perfect for an emotional climax, as Prince breaks down wailing “I beg you down on my knees/I want YOU.”
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Step 5
Top it all of with another of your loved one's favorites. Something touching but not too depressing. You want a ray of hope at the end, naturally.
