The first thing I think of when I hear this song and see the title for it is the Dashboard Confessional song which has the line "I never said don't go (don't go)". It's something about wanting someone to stay who wants to leave. Do you let them leave? Do you feel like you're holding them back by not letting them go? It's a situation I feel like we've all experienced in our lifetime. In my youth when I was dating I remember thinking it better to let go instead of staying in those empty relationships so in that sense I was likely on the other side of this song, which, again, something we all have likely also felt.
There is a music video for this which just presents various images that look like they have filters and move like an old movie. There is a silhouette of what appears to be a person but it does not come through fully. I feel like this represents that idea of someone stuck between staying or going because even though this song is presumably asking someone not to go it is unclear as to what the decision of that person is.
With the soft voice of Vicky Sjohall you will find pianos and the occasional added vocals by Geoff Gibbson. This song has an acoustic, relaxing feel to it like The Beatles "Hey Jude". At the end it all comes tied together with strings but this just has that big feeling even before that- where even though the music itself can feel simple with only a piano it has that complex/orchestral type of way about it. In its tone though, it is a sad song and so I'm not sure when you would best be listening to this song other than when you have feelings of sadness.
Though I will not say this with 100% certainty I feel like the radio has shifted away from songs like this. You don't really hear the slow, sad songs as much any more. I remember when Whitney Houston covered "I Will Always Love You" for "The Bodyguard" soundtrack and it seemed like it was always on the radio. Now, unless you have a beat or guitar it feels like you won't be on the radio. I can't think of the last time I heard a sad song like this on the radio but it would be a nice way to break up your day. I imagine it coming on in a public place, everyone just stopping what they're doing and reflecting.