A 7 Step Guide To The Art Of Mixtape Making

Christian De Neuvillette had Cyrano De Bergerac; my high school winter ball date had Alexi Murdoch and Train; Lloyd Dobler had Peter Gabriel and, at varying times and in certain situations, I’ve had Stephin Merritt, Stuart Murdoch, Jeff Tweedy and a revolving cast of singers and songwriters who ostensibly express me better than I ever could, even when I’m on Bitters & Absolut.

I had been on mix-making hiatus for about four years before this fall, but it used to be an integral part of my dating (and attempting to date) life, almost laughably so (read: definitely laughably so). However, somewhere between junior and senior year of college I went cold turkey. Somehow, some way, it seemed almost counterproductive, maybe even a little overwrought, and certainly unnecessary. I mean, not that it is… it just seemed that way. It’s an art after all.

Recently, I fell off the wagon and made two: one that I sent, and one that I didn’t. I could blame extenuating circumstances, or playful irony, or even that, you know, she literally asked for it. But those aren’t really the motivations behind mix-making, and it pains me to say that I don’t think they ever have been.

What does one seek to accomplish with a compilation tape, let alone a great one? Well, for one thing, like Christian De Neuvillette or my winter ball date in high school, to say something in a creative and more fully realized manner to someone. If Lloyd had simply told Diane Court that he saw “the light and the heat in her eyes,” it wouldn’t have birthed a thousand grand, romantic, copycat gestures. An unsung but big part of making a mix is a proper package; standing outside with a boom box was just his meticulously sharpied jewel case. Think of it as twee peacocking.

Now, I didn’t think about it that way at the time. Sure, it was obviously a presentation, but, in my mind, it was meant to illicit a specific, knowing reaction, never to create a flex zone.

See, I did it all to get the girl, man! No way she wouldn’t notice the subtleties of the song order. And when she did, it’d make all the difference. “Hah,” she’d say, with an emotionally charged glance out the window, “I see what he did there. ‘With A Girl Like You’ and then ‘This Little Ukulele.’ That really is the story of us.”

If any girl I’ve made a mix for has done something like that, I hope she reads this and tells me, because that’s a lifetime of validation.

Unfortunately, when I was all: “‘A Pretty Girl Is Like…’ followed by ‘Whiskey River (Live)’ is gonna start this catharsis off right! She’ll see that nothing’s changed between us, nor ever will,” it was much more for my benefit than it ever could have been for hers. As much as there should be more split-screen, mutual recognition montages in real life, things usually fail to play out that way. No one reads into things as much as you’d think. To be fair, this is often a good thing.

That being said, if you are so inspired; if you’re thinking: “Maybe surprising girls at their doors in the rain is how Taylor Swift thinks I’ll win her over, but I’m pretty sure a well placed troika of the Mountain Goats, Postal Service and Future Bible Heroes will get the job done;” or if you’re just looking to show how well you can apply the sentiments of strangers to your own life, here’s how I’d go about it:

Before you even start, make sure you’ve watched High Fidelity five times a year for thirteen years, or at least once. To quote the old gawd, Rob Gordon (that’s two John Cusack characters for those counting at home): “the making of a great compilation tape, like breaking up, is hard to do… There are a lot of rules.”

1. The first track is important. This is your “Call Me Ishmael” moment. The hook has been baited, but now it’s time to solicit a bite. Nothing too long here, but make sure it kicks ass: you’re convincing someone to listen further. If you’re stuck, just pick a top five favorite of yours (though not probably a top one or two). It’ll set a confident tone.
2. Here’s your first big opportunity to show off your sense of flow. Maybe a slight pause after the end of the first song to emphasize whatever brilliant crescendo you’re bringing into play.
3. Through the first two songs, there’s really no reason to go all in on the message you’re trying to send. This is where you start to introduce it. This should also be the next logical extension of whatever sonic theme you’ve built up with the first two. The first wave hits the beach on track three.
4. This should be the first time you throw in something a little longer and probably a little slower. I guess you can do that third as well, but it’s ultimately more productive to wait for the clean-up spot. After all, your execution has been flawless up to this point, why take a short cut?
5. So remember how you started pushing what you’re trying to get across with track three? Here’s where you really commit to the bit. Personal history, inside jokes (hopefully you have some of each), that’s the territory you’re in now. She’ll definitely remember the good times.
6. And now you repeat one through five two or three times. When and if you hit fifteen songs, I’d cut off your curation. This is a love letter, not a jogging playlist, although the relative efficacy may be debatable.
7. Listen through, get your transitions on point, and prepare to steal a heart!

It’s hard to admit, but making a mix is about chasing a muse, not actually fostering a relationship with a human being. It’s like writing a poem specifically for someone and having them read it in front of you (if anyone does that. I certainly wouldn’t know and can only guess). They may appreciate the gesture, they may be flattered; they might even like it and sort of kind of allow you to briefly infer that you’re dating, but ultimately, you didn’t really achieve a stronger connection. Sometimes just getting your feelings straight is an accomplishment in itself. That form of creative expression may have been exactly what I was doing. Catharsis indeed. Ultimately though, telling someone how you feel is better left off the page and the CD, and more successfully expressed in person, using no one’s words but your own.