What is it about making mixes that’s such a kick in a glass? Sure, there’s the whole look-how-much-obscure-music-I-know dynamic, but that’s only a fraction of it. As fun as it is to assert your hipster status via a bomb-ass party playlist, the pleasures of mix-making far transcend the social sphere.

There’s something immensely gratifying about compiling a list of songs you absolutely love and having them flow seamlessly together as a unit. When you christen a list of five-star tracks under a snappy title like “Romantic Cynicism” and listen to your masterwork on a long car ride, it’s hard not to feel like you wrote the music yourself. It’s the same kind of rush us music bastards get from meticulously culling our top-five favorite albums of all time. While we may not have personally composed the songs or records, there’s an inexplicable satisfaction in knowing that these are “our” picks, “our” essentials. Mixes are just another way for us to jerk off our self-righteousness. Or, in slightly less cynical terms, they help us to therapeutically solidify our identity.

Whenever I come home ripped after a party, I’ll make a beeline straight for my iPod and immediately begin crafting an On-The-Go playlist (despite the fact I’m going absolutely nowhere, other than to bed). I’ll spend 20 to 30 minutes under the covers, gleefully skimming my thumb over the dial, plowing through my entire library to hunt down songs “I absolutely need to hear right now.” Then I’ll spend an additional 15 to 20 minutes chiseling down my list to 15 songs (yes, I’m compulsive about this number) that “work” together.

By the time I’m done with this procedure, my high will have always completely worn off and I’ll listen to approximately one song and pass out, wondering why I didn’t just listen to Radiohead. This scenario repeats itself almost every weekend. I love mix-making so much that I make mixes I never even listen to.

But as much as I gush over the art of mix-making, I must admit that — as with everything in my life — the process comes equipped with its fair share of neuroses. For instance, I’ll survey my collection of playlists on my iPod and worry I’m reusing the same bands too often. Should I really have a Broken Social Scene song on every single one of my playlists? Doesn’t that make me look like too much of an “indie kid”? Shouldn’t I throw in at least one song that wasn’t released in the last 10 years? Shouldn’t I be drawing upon my seasoned knowledge of music instead of predictably slopping down tracks by the same 20 or so bands (the ones on my Facebook “favorites”)? It doesn’t matter that I’m making these mixes for my own enjoyment; I am perpetually plagued by an elitist Jiminy Cricket.

And these self-induced pressures are magnified 10-fold when I’m making a mix for someone else: What if the person already has this song? Then the person will just skip over it every time he or she listens to my mix; that’s a waste of a song. That’s a waste of one-fifteenth of my mix. Maybe I should put on a more obscure song — something by Sonic Youth. But this one has a noise intro and the intended recipient will probably get bored and just skip to the next song anyway. And so on.

Then there’s the type of mix-making that’s both the most nerve-racking and the most exhilarating: The kind where you craft a mix to try to get someone to fall in love with you. These mixes are incredibly tricky; you have to make the mix romantic enough so that the seed is planted, but not so sappy it’s overkill. Although it’s technically not you singing the lyrics in the songs you compile, you’re making a statement by selecting these particular tracks.

Hiring Ira Kaplan of Yo La Tengo to croon “We’re on our way to falling in love” to someone you haven’t even French-kissed yet can be risky business. Sometimes the best tactic is to balance out the mushy songs with a few “fun” songs that let the recipient of your mix know you’re not about to propose. Or you could always just play the hopeless romantic card and throw in a handful of jaded “love” songs ala Elliott Smith. Lyrics like “The moon is a sickle cell / It will kill you in time” are sure to reveal your sensitive side without laying on the schmaltz.

Some people don’t take mix-making all that seriously, however. I once received a mix on which roughly a third of the songs were by John Mayer (as far as I’m concerned, featuring the same artist more than once on a mix is strictly forbidden — unless, of course, you use the artist to bookend the compilation). But in this postmodern world, when it can be argued that true innovation is practically extinct, the painstaking collaging of other people’s work can be employed as a pseudo-legitimate art form (just ask Girl Talk or John Cusack in “High Fidelity”). Hell, if Andy Warhol can make a Campbell’s Soup Box and call it art, then what’s to stop my 15-track playlist from making me feel like a badass?

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