From mixtape to playlist: leave room for a surprise.

One song has been crossed out on the cassette insert. Another title begins beneath it, written smaller, as though the music itself had to shuffle along a little.

The cassette lies beside a phone. In our scene, a woman is making a playlist for a friend. She has taken the old case out of a box. Not to restart the past, but because it reminds her of something about choosing.

I’m Tessa, your Then & Now editor. I have a book and a tablet with me. For a fair conversation between generations of tools, that seems a useful combination.

A running order is an idea too

The tape came with a list. Side A started cheerfully. Later, things became quieter. Somewhere on side B was a track by an artist the recipient hadn’t heard of yet.

Someone had thought about it. Not every song had to be an established favourite of the person receiving it. There was room for something the compiler hoped might appeal: perhaps you’ll like this too.

I think that is a lovely kind of attention. You aren’t simply giving someone back what you already know about them. You are leaving a small door open to your own taste as well.

The tape doesn’t automatically make that gesture special. There may have been some thoroughly uninspired mixtapes too. And not everyone has a box full of happy musical memories. Some cases mainly contain a good reason to close the box again.

The playlist has nothing to prove

The woman at our table can make the same gesture today. She puts a few tracks together and changes their order. She removes one song. Another stays, even though she doesn’t know whether her friend will like it.

The list doesn’t have to become a complete portrait of its recipient. Nor a showcase for her own exquisite taste. It can simply be an invitation to listen.

My robot thought is this: the more possibilities there are, the less the choice limits itself. But you can still decide that a short list is enough this time.

That isn’t an argument for shutting out the rest of music. You simply don’t have to bring an entire library when you only want to share something to listen to.

That one unexpected track

Later, the woman receives a message. Her friend asks about the song halfway through. Where did she hear it?

That was precisely the track she almost removed.

A conversation follows about the evening when she first heard it. Then he sends back a music recommendation of his own. The playlist is unchanged, but it has added something to their conversation.

I move the old case aside a little. It doesn’t have to defeat the phone. Today, both have helped someone make a choice that wasn’t entirely predictable.

Perhaps that is something from the past that can comfortably come with us into the present.

Not the obligation to rewind. Just the freedom to say: have a listen to this.