At the risk of sounding like a Nick Hornby character, creating a mix for someone is a delicate task. It has to be eclectic, but you also want to cater to the recipient’s tastes somewhat or they won’t actually listen to the thing. It probably shouldn’t contain any tracks off Weezer’s Pinkerton, but it has to be obvious that you’re making this person a mix because you like them and not because you’re a pop evangelist attempting to impose your tastes on them.
It’s long been my personal opinion that mixes are the greatest Valentine’s Day gift of all—they indicate a certain degree of effort, which is always more meaningful than a box of chocolates or a card with a pug on it from the grocery store. They’re not too corny as far as romantic gestures go—making someone a Valentine’s Day mix allows you to acknowledge the holiday without forsaking the anti-materialistic position you likely purport to hold.
Mixes are great; I love making them and I love receiving them. They are also hard. I’ve spent entire days toiling over track substitutions and trivial sequencing decisions. Of course, a lot of what makes a great mix is subjective—but there are a few basic guidelines you always want to follow no matter what.
Choose a format.
There are some insufferable purists who insist that mixes are only legitimate when they’re impressed on some physical format. This is really weird to me, since in my experience, producing the actual mix itself—whether it’s a playlist, tape, or CD—is the easiest part of the entire process. If you both have Spotify, then that’s obviously the easiest method. That said, I used to buy Memorex CDs and Sharpie out the letters so they said “emo.” Funny stuff!
Figure out what you’re trying to express.
It may seem like making a romantic mix for someone is as simple as throwing some love songs on a playlist—for the “I don’t really pay attention to the lyrics” crowd this is possibly sufficient, but under any other circumstance it won’t fly. It’s important that you tailor your mix to your unique situation.
For example, a couple of years ago I returned to Portland after a failed stint in Los Angeles as a copywriter for a niche Jewish marketing agency where some of my duties included writing newsletters about Matisyahu and leaving messages on Mike Huckabee’s voicemail. I started sleeping with an old flame while her boyfriend was banging pots and pans together at a musique concréte artist retreat in Switzerland or something, and I feel like I can safely publish this because me and this person live together in a very messy apartment now. The mix I made for them had to encompass these three themes: my big return home, my desire to properly rekindle a romantic connection and last but not least, clandestine sex. Naturally, I included “I Want You Back” by the Jackson 5, “The Boys are Back in Town” by Thin Lizzy and “Little Red Corvette” by Prince among others.
This point works both ways—if you’re comfortable with this person already and you’re using a mix to strengthen your bond, then it’s helpful to be sort of explicit. On the other hand, if it’s mostly puppy love and you’ve only been on one or two dates, I would steer clear of Prince.
Keep an eye on the runtime.
Do not make a mix that is absurdly long—10–15 tracks is reasonable and 20 should be the absolute maximum. The mix should be a demonstration of your feelings in the form of songs you both think are good, not an opportunity to flaunt your familiarity with the pre-amitriptyline Nick Drake oeuvre.
Include at least a couple of horny songs.
Listen, we’re all adults here. A mix ideally runs the gamut of human feeling and one of these feelings is horniness. It shouldn’t be overwhelmingly horny or creepy, but you should probably include at least a couple of songs about sex so this person doesn’t just think you’re courting them to be your rock climbing buddy or something.
Always include “Silver Springs” by Fleetwood Mac and/or “Hot Burrito #1” by the Flying Burrito Brothers.
Full stop. Either one of these bring the house down each time, and they’re perfect for the penultimate slot. Some people pay thousands of dollars for the wisdom I’m imparting here.
Avoid famously cancelled artists.
I used to not believe it myself, but you can make a perfectly good mix without “Girlfriend” by Michael Jackson. A mix for someone you like is no place to take a stand on the art-versus-artist dilemma, regardless of your personal philosophy. It’s a nonessential risk, and worst case scenario, the recipient will think you’re sort of a flippant asshole with a questionable moral compass.