Play On, Playlist: A Guide To Avoiding Mix Tape Mistakes

So you’ve met someone. And you like her. Or him. It’s an old school, stomach-twisting crush. As an adult, you’re not really sure how to reach out. Isn’t it a little awkward to ask for the number of the cute bartender in your neighborhood just because you have a good rapport?  Does anyone send flowers anymore, or does that mean you want to be engaged?

The classic, low-pressure move in this situation is the mix tape. Which I think is a misnomer in most cases. Probably you’d be working with a mix CD. Or a digital playlist. I’ll say mix tape because of some romantic ideal I’m still holding that there’s a mystical aphrodisiac power in an actual, physical cassette.

A mix tape is a thoughtful, yet noncommittal gift. It says, “Hey, let’s hang out sometime, but it won’t be that weird if we don’t!”  Which, granted, is not the most romantic of messages, but it’s a start!  Even with something as friendly and low-pressure as a mix tape, though, there are certain pitfalls to avoid. Here’s a guide to sidestepping the most common mix tape faux pas:

1. No Songs with “Love” in the Title

At least in reference to a person. “I Love Rock and Roll” would be okay. But “Somebody To Love,” nope. And Whitney Houston’s “I Will Always Love You” is instant mix tape death. Also, anything about marriage. “Happy Together” and “Wouldn’t It Be Nice” are a little too wedding-y. Yes, I know it’s great to have a crush. But don’t squash it with over-amorous overtures. You might as well just stand outside his/her window and play the whole thing on a boom box if you’re going to go there.

2. Nothing Everyone Already Knows

It’s fine to slip in a few songs that sound familiar. Just avoid what I’d call “Karaoke Standards.”  No “Livin’ on a Prayer.”  No “Don’t Stop Believing.” Your new crush will think you have all the originality of a Monster Ballads compilation advertised at 2 AM on the Cartoon Network. If you’re going to slip in a classic, make it something a little further off the beaten path. If you must include some Journey, go with “Lights.” Avoid “Wheel in the Sky.” I think that’s about Jesus. I can’t say that with one hundred percent certainty, but I’m not going to listen to it to be sure.

3. Nothing Too Dark

A friend told me he once unwittingly included “Possum Kingdom” by the Toadies on a CD for a girl he was dating. You know, that one song that climaxes with several shrieks of “DOOOOOO YOU WANNA DIE?” Big mistake. Keep it light. You’re angling for a date, not a new member of your suicide cult. I don’t care how much you love Metallica. If you include “Enter Sandman,” your chances of getting lucky will be off to never-never land.

4. Don’t Go Overly Sexual

I don’t care how much you like this new person. It sends a very specific message if you decide to include “I’m A Slave 4U” on the playlist. I’d also leave off anything by 2 Live Crew and any song recorded during Jay-Z’s short but enthusiastic “ecstasy and threesome” phase. I mean, unless you’re just trying to send the message that you’re down for whatever, whenever. Then throw all those sex jams on there. And bookend it with the “Whatever, Whenever” by Shakira. And write out the tracklist on a thong.

5. This is NOT An Advertisement For How Cool You Are

Seriously. You’re making a playlist for someone else to enjoy, not for them to see how indie you are. Maybe she’s not going to be into those unreleased Frank Zappa demos or Animal Collective b-sides. Perhaps he doesn’t care about what band Win Butler was in before the Arcade Fire. We get it. You’re hip. Unless you think the song actually sounds really good, no one cares about what time signature it’s in. Seriously. Throw some Prince on there and keep it funky.

This is not a set of hard and fast rules. If you are a goth making a mix tape for another goth, perhaps Marilyn Manson’s “Sweet Dreams” is a blast of welcome nostalgia and not a creepy sign to run for the hills. If you work on the docks in your hometown, by all means, load it up with the Bon Jovi. If you both have horrible taste in everything, throw a Daughtry track on there.

Obviously, cater to your own tastes, and most importantly the tastes of the person you’re making the mix tape for. These simple rules will just help you avoid a minefield of wildly inappropriate songs.

Now get out there, and start making out! TC mark

image – Cassettes


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  • tash

    man, the toadies rule! any guy that doesn’t appreciate “possum kingdom” on a mixed tape I make for him isn’t even worth my time of day!

  • Tau Zaman

    Mixtapes are a romantic art. And it’s so hard these days because now the exchange of music is so…transactional?

    For example. Your crush will be like, “Yeah, I totally love your taste in music!” And you’ll make some comment about how you should totally jam out together, or something, using less lame words than that. And then they’ll be like, “Give me everything you have!” And well, there’s only one efficient way to do that: on a flash-drive? Well, um, okay. Here’s 4,000 tracks with several full albums that took no thought to put together.

    • flipside of a memory

      I agree!

  • Jaime Wright

    If the guy you have a crush on is in a band, and it’s your favorite band- don’t give him a mixtape of his band.

    • Tau Zaman

      I think there’s some unwritten rule that your crush’s band just cannot be your favorite band.

  • Samie Rose

    The music examples in here are douchey.

  • tracy

    HAHA #5 “Unless you think the song actually sounds really good, no one cares about what time signature it’s in.  Seriously.”

    That was awesome.

  • Anonymous

    Don’t forget the Nickelback!!!1!1!

  • flipside of a memory

    haha, #1 is the best.
    Anyway, I used to love making mixtapes/cds but I have not made one
    for a long time primarily because music seems so accessible these days
    and if you have the same music taste (more or less) there’s a big chance
     he/she’s already heard it, nevermind if it’s that obscure northern soul
     classic, or the latest pop tune. Sure the whole mix would still be
    different, but now the actual gesture seems futile,  you can just mediafire it right? *sads*  No one has made me a mix for a long time and I really miss it.

  • Mauricio

    “If you include “Enter Sandman,” your chances of getting lucky will be off to never-never land.”

    I think I just peed myself.

  • a.

    “This is NOT An Advertisement For How Cool You Are”

    …Oh god. I think I tend to fall into this category.

  • Tanya Salyers

    “If you both have horrible taste, throw a Daughtry track in there.”


  • SweetT

    I disagree with the “noncommittal gift.” It’s so committal. Too much so, even. I’ve never regretted sex, but I’ve regretted mix tapes.

  • Gregory Costa

    I tried using the cassette player in my car for the first time the other day to play my dad’s Talking Heads album…had no clue how to work the thing. 

  • Anonymous

    I got a mix tape from a boy that made four out of the five mistakes outlined here, BUT it ended up being actually a really great mix tape. I still listen to it. But man, nearly every song was like “I haven’t had one pure thought since I saw you” “let’s fall in love and have babies” “I’ve been in love with you forever” so at first, I was real creeped out. But now I’m like, “hey wanna listen to this really great mix tape I got once?”

  • kaylee

    oh god, daughtry. make it stop

  • kaylee

    oh god, daughtry. make it stop

  • Anonymous

  • Kodi

    Its all about the flow from one song to the next. 

  • Anonymous

    This is the most hilarious thing I’ve read on TC in weeks.

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