music

Journaling Questions for Music Lovers

you look pretty sad for a girl so in love

Olivia Rodrigo, 2026

Journaling questions paired for listening with Olivia Rodrigo’s new album, you look pretty sad for a girl so in love.

  1. ‘drop dead’ features the heightened feelings of a new love. How might the feelings of new love change if your adrenaline decreased?

  2. ‘stupid song’ captures the feeling of having an emotion so big that it defies description. What feelings have to make themselves smaller for the one you are experiencing to have enough room?

  3. ‘honeybee’ paints the picture of a love so valuable that you can't help but worry about losing it. How vulnerable are you willing to be in front of another for a love that valuable?

  4. ‘maggots for brains’ is a fun song about focusing your attention on a single person. What might be most exciting about a dynamic like this never changing? What worries you?

  5. ‘u + me = <3’ reminds us that change can feel scariest when the right-now is so great. What might it be like to imagine our loved ones changing in a way that excites us?

  6. ‘my way’ sends a clear message that there are certain social boundaries that we should respect no matter what. Have you ever been in anyone’s way? How did you get there?

  7. ‘purple’ is a great metaphor for getting lost in our admiration for another person. What parts of yourself are hardest to see when in ‘purple lighting’? Are those parts ok with being hidden?

  8. ‘the cure’ unites us all in searching for that antidote that would suddenly fix all of our flaws. What would it be like to imagine that there was nothing wrong with you in the first place?

  9. ‘begged’ draws from an assumption that "it's a virtue to not let good love slip away." Would you still be so wrong for letting a good love slip away if love was the only good part?

  10. ‘what’s wrong with me' asks a scary question that begs an even scarier one: What happens if you do nothing right now?

  11. ‘less’ reminds us of the deep pain that can come from love leaving. What if allowing yourself to be loved without the promise of forever despite all the past pain meant you were being brave? Can you imagine a story where to do it again would be even braver?

  12. ‘expectations’ reflects on a transformation in attraction, from being dazzled to having discernment. What do you think used to feel most attractive about the things you no longer desire?

  13. ‘cigarette smoke’ asks the question of whether we should regret the things that hurt us. Can you consider that it was actually really brave of you to try, even if the result was not what you hoped? Can you imagine a story where it would be even braver to try again?

Questions compiled by Sayftee therapist, Emma Bowe-Shulman.