The Fine Art Of Mixtape Seduction

Mixtapes are really flattering self-portraits, but the best ones are selfies of two.

Summer Anne Burton

I have always given my crushes pet names: a never-revealed infatuation with my friend “Married,” the waiter “Seconds,” a future boyfriend “Twelvest,” and someone who I would eventually come to refer to as “Purgatory” to his face.

I named “Wilco and Breakfast” that because of how I imagined our future together — listening to Summerteeth on vinyl while smoking cigarettes and drinking coffee in bed. “His beard makes me feel like he’d make good pancakes,” I told my roommate during one of our countless conversations about the boys I was considering hitching my crush wagon to.

Wilco and Breakfast was a co-worker, but in a different department so it was a mysterious and slow-moving courtship. He maintained a soft reserve throughout his tenure. He was always kind, but never really hung around to get to know his colleagues. He had a round face, ruddy cheeks, broad shoulders, and that beard, which probably accounted for at least 60% of my reasons for crushing. He was several years older than me and a musician. A musician with a rumbly Southern drawl who would sing his songs about girls in the corner of some Tex-Mex restaurant once a week.

I didn’t stand a chance.

I’d wait for him to clock out for his cigarette break and then go out for mine. I’d sit next to him, pretending it was a coincidence, and we’d chat about the easy stuff: books, movies, songs. We shared a weakness for sad stories and vintage anythings. At some point, I loaned him a copy of one of my favorite films — David Gordon Green’s All The Real Girls, and he wrote me a short email the next day saying “I loved it. I loved it two times.” I found those two sentences so charming that I showed the email to half of my co-workers.

At some point I became confident that my feelings were, at least in some part, mutual. Wilco and Breakfast had a thing for vintage pinup girls — I knew this because of MySpace — and he would compliment my knee high socks or my slouchy trench coat in this certain way that felt like a wink. He would occasionally use the word beautiful — as in “you look beautiful today,” or “that dress is beautiful,” which knocked me over because boys my age never called anything beautiful, especially girls that they barely knew. It was all very fun and exciting and sweet, as requited crushes tend to be.

My next move was obvious: I made him a mix.

Summer Anne Burton

Someone told me once that mixtapes are barely about music at all. They are about which songs you hope will be forever linked to your face and subconsciously understood as your intentions. Mixtape making is flattering self-portraiture — like choosing the perfect selfie to express how funny, sexy, light-hearted, or endearing you are…preferably all of the above.

I have been working at this art since I was 16, crafting hundreds of meticulously chosen mixtapes, CDs, and playlists for best friends, foxy boys, friendly co-workers, and various bad decisions. I’ve learned to embrace the vanity of mix-making while also making mixes that people really want to listen to. I’ve been doing this so much — more than any other creative pursuit — and for so long, that I’ve started to think that mixtapes have become my purest self-expression.

The only way I know how to feel something is to make a mix about it.

These days, finding someone who actually listens to cassettes is a white whale, so I have switched to Spotify and gift-wrapped CDs. It’s fun, but not quite the same. Making someone a cassette was so personal because of the time you had to spend with the songs, sitting in front of a cassette player pushing buttons and obsessing over whether the song you wanted would fit on what was left of a side. It was different for the listener too — cassettes don’t make it easy to skip tracks, so they’re forced sit and listen to what you have to say.

My box of tapes from high school. Summer Anne Burton

I have very specific rules about crush mixes, having made a fool of myself with tape after tape as a teenager. The ONLY AND IMPORTANT AND UNBREAKABLE RULE of a crush mix is that crush mixes are not allowed to have songs that are explicitly about having a crush. The crush mix — markedly different from the “good first date” or “new relationship” mix, mind you — is not an actual confession so much as very advanced flirtation. It’s a whisper that someone should be leaning in to hear, not a love letter blasted through a megaphone. I adhere to this rule despite the constant temptation of The Clash’s “1, 2, Crush On You” or the Joan Jett version of “Crimson and Clover.”

Crush mixes can, however, include songs about all kinds of other things that evoke the feeling of having a crush. Songs that are too cryptic to extract any obviously embarrassing meaning from, but which exude important vibes. Vibes like “easy-going,” “I am your dream girl and you haven’t yet realized it,” “I’m probably into whatever it is you were thinking about proposing after a few beers,” and “someday we will be old together and all of these songs will make us remember what it was like to be young and about to be in love.”

Summer Anne Burton

Despite my adherence to the rule, the fact I was already planning dream breakfasts with Wilco and Breakfast when I gave him my mix was fairly obvious. The cover was hand-designed, some of my most beautifully evocative mixtape cover artwork of all time. There was a hand-stamped title, a collage of birds and telephone wires. I was so proud of how I’d pulled off that crush feeling and that flattering self-portrait on this mix that I even made an extra copy for my roommate — it was just too good to keep between me and a guy I barely knew.

Wilco and Breakfast and I never actually made it to breakfast. The mix “worked” but we didn’t. He loved it (presumably even more than two times), but when we went on a halfway-date it ended with him kissing the top of my head. And that was all. The anticipation, as usual, more fulfilling than the execution.

I was sitting at my favorite coffee shop months after the crush had anti-climaxed and I heard a song I loved. And then another, and then another. When the order seemed all to familiar to ignore I asked the barista what mix he was playing. “Oh, I don’t know who made it but it says ‘Wilco and Breakfast’ on it and it’s the best mix ever.”

Summer Anne Burton

I was determined to weave a mood rather than make my infatuation explicit, so I followed the rule pretty closely. Many of these songs are about loneliness, depression, death, and sleeplessness. That might seem counterintuitive but mix-making is all about reading people. I perceived that Wilco and Breakfast was kind of a serious dude, and one of the dozens of tiny messages I wanted to send was that I could totally handle that shit and was in fact often very sad myself. One of the sexiest things in the world to someone who’s been through some bullshit is someone else who is ready to hear about it.

The mix had to be cool too — I included David Bowie and Velvet Underground: songs that he had definitely heard, probably already liked, and would a signifier of my coolness and deep understanding of guys who are into Betty Page. And there were extra personal notes — the Josh Ritter and Will Johnson songs reminded me of the songs he wrote himself. I’ve since figured out that musicians, like artists, don’t actually always appreciate the work of people who are doing what they do but more successfully. The Songs: Ohia song “Just Be Simple” is a signature mix track for me — I think of it as a litmus test. If you can hear that song knowing that I relate to it deeply, maybe you can handle my worst self someday.

There was plenty of provocation and flirting on this mix, but it was buried within songs about other things. “I’m wearing sleeves on my heart for you,” in the middle of a Neva Dinova song about dying. “I feel insane when you get in my bed,” is overt, but it’s in this song by the Silver Jews that’s mostly about monsters and ego. Okkervil River’s Will Sheff sings “and if you want it to be real, come over for one night, and we can really, really climb,” but then the song turns terrifying.

The mix ends with “I Go To The Barn Because I Like The” by Band of Horses. Closers are a last opportunity to say what needs to be said, and “I’d like to think I’m the mess you’d wear with pride” is the most direct and honest line regarding my actual feelings on this entire mix. Even after Wilco and Breakfast and I fizzled uneventfully, I would sometimes listen to this song and picture him in the song’s “worn-out suit and tie” and feel wistful.

Back to what my friend said about mix-making being flattering self-portraiture disguised as a gift: I think maybe that’s true, but the best mixes are selfies of two. Sure, you want these songs to form a picture of you, but they form a mirror as well. Good mixtapes take time and energy and effort and thoughtfulness. Making one for someone tells that person they’re important to you, and preserves a fleeting feeling that might have have otherwise been forgotten.

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