Let me preface this by stating outright that there are better ways to go about wooing the female object of your desire. In most cases, being yourself will do the trick. There is no substitute for self-confidence, and slyly passing along a once blank CD upon which you poured your heart and soul to a near stranger will only win you an awkward look – or a restraining order. However, a well thought out mixtape, delivered at the right time, can be a very romantic gesture. Whether you are courting a girl or have been dating her for quite some time, there are a few simple preliminary rules we should go over before I delve into our first lesson in the art of mixtaping.

First, you should never, never, ever create a mixtape for someone you LITERALLY JUST MET. A mixtape is supposed to say something, either about her or yourself, and there is nothing of romantic value that you can possibly need to divulge after spending twenty-five minutes chatting at the food court and sharing a Wendy’s frosty. If you come on too strong, you, like that frosty, will soon be nonexistent in her eyes, capisce? Okay, now that we have established what was hopefully obvious, let’s take a look at rule number two. PERSONALIZE IT. The trick is that you want her to think of you when she hears the songs, so try to steer clear of more popular items that she may have already associated a memory with. Besides, there is nothing worse than making a CD full of your favorite Ke$ha jams because not only is it thoughtless, but it is not a mixtape – it’s called NOW #infinity. So do both of yourselves a favor and spare her the radio hits – I’m sure she knows her way around a knob. Also, if she can’t appreciate a song with a run time of over four minutes, she’s not the kind of shallow person you want to impress anyway. Third and finally, think PACKAGING. A shiny silver disc is alright on its own, but putting some thought into the display shows her that you are willing to go the extra mile. Just don’t get too festive or she might start introducing you to her guy friends.

We all know unicorns are fucking awesome, but they have no place on your mixtape's artwork.

Alright, enough of the appetizers, it’s time to get into the meat of our lesson. As you know, there are a lot of different types of chicks out there. Big ones, small ones, young ones, and old ones. Knowing your subject’s likes and dislikes are paramount; you don’t have to know her exact taste in music per se, but learning a little about her personality can go a long way in your efforts to predict what she will find alluring and what she will reject with the force of Gerard Way pushing and kicking away from a pair of breasts at a strip club. There are obviously no guarantees, but that is what makes it such an interesting gift. If she gives you positive feedback about track 3 and track 12, then you can look into those and explore opportunities for her next auditory adventure. Oh, and that brings me to two other rules: (1) never say auditory adventure, and (2) don’t bombard her with CDs! She needs time to digest them and form opinions about just how much she loves the songs or hates them. A good time frame would be two per year, maximum. You want her waiting in anticipation for the next installment, not pushing through them like a goddamned homework assignment. It should also be noted that it is never necessary to make more than one mixtape; I have always found it best to stop after one and then only continue upon request. There are two reasons for this. First, if she likes it enough and is really into you, she will probably ask for another one. Second, if she didn’t enjoy it, shoving more of your shitty music in her face is going to be frustrating and annoying, even if she does like you.

Our first observations will be of “the average girl” and the “indie chick.” They may seem very similar, but there is a distinct difference: the average girl thinks Lynyrd Skynyrd is a person and doesn’t appreciate the raw, impassioned beauty of Bon Iver. While the indie chick may have those two things nailed down, she also holds an unparalleled ability to be a snobbish bitch. If anything, she is more likely to tell you off for listening to Justin Vernon’s random hummings and chirpings now that ‘Holocene’ has been recognized as a 2012 Grammy nominee (it’s true, check iTunes). So to make a long story short, here is a brief sampling of songs that may work for either girl. I know…metal chick, biker chick, nymphomaniac, etc. have all been excluded from this edition, but no worries – advice is on the way in the near future. But for now, if either of these genres of girls appeal to you, I hope these samples will serve you well:

The Typical Girl

Example: Anna Kendrick. Not that I know her personally, but she was in Twilight, and that seems pretty typical for a girl.

The average girl, for what my experience is worth, likes melodic and meaningful music that isn’t too challenging. For example, Iron & Wine’s “Flightless Bird, American Mouth.” It’s soothing rhythm and vaguely romantic chorus make for the ideal mixtape closing track:

“Flightless Bird, American Mouth” (Iron & Wine)

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Not everything has to be a confession of love. Sometimes songs about love and its tendencies/importance can leave just as strong of an impression. For a more upbeat song to add to your mix, “Always Love” is an excellent choice, featuring an irresistible chorus and lyrics that will be sure to make their way to her facebook status.

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Another catchy number with loads of gorgeous imagery. Waking Ashland is a great “average girl” band because all of their songs are so emotive and simultaneously infectious. “October Skies” is the cream of the crop.

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The indie girls are where you really have to watch your step. One wrong move and you could find yourself at the mercy of her and her stylish hat, trendy handbag, and sewn-on backpack patches. You want to be a lot more subtle about your motives, let your feelings speak through the music rather than blatantly through the lyrics. For example, Fleet Foxes’ “The Cascades” is a waterfall of breathtaking acoustics that have no vocals at all to ruin the beauty of the moment:

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“Search Lights” sounds like an unreleased Shins song, but it is geared more towards heartfelt imagery. Imagine if “Sea Legs” was a romantic ballad, and you basically have this stunningly picturesque work by Empress Hotel.

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“The Other Side of Mt. Heart Attack” (Liars)

This is a riskier inclusion than either of the other two tracks because it is so damn depressing. After all, that shouldn’t be the goal of your mixtape. However, there is beauty under the surface here, with breathtaking atmospheric hums and gentle reassuring chants of “I won’t run far, I can always be found…If you need me, I can always be found.” I’m convinced that the right “indie chick” would fall in love with this song and what it represents.