
Falling in love is an experience that can bring up conflicting feelings. Sometimes, we are able to dive right in and embrace the vulnerability that comes alongside being in a committed relationship. Other times, we feel the need to protect ourselves by keeping our romantic interest at arms’ length. Almost always, the level of emotional safety we feel depends largely on what the other person is able to offer. These two songs highlight the contrast between two very different relationships, but are both incredibly heartfelt in their own way.

“Back In Town” – Annie DiRusso
“Back In Town” is a song about falling for someone who can’t give you what you need, forcing you to lower your expectations and proceed with caution. From the song’s opening lines, “Swore I would take to my grave the fact I changed my flight / out of Chicago just so I’d see you one more time,” it’s clear Annie cares about this person, but is also guarded. Even though she has strong feelings, she does her best to hide them and make herself seem like a chill, cool girl. Realistically, she knows she is going to continue being disappointed by this person, but is still holding out hope they might become the partner she needs (“When you’re back, you’re back”). While she cares more about them than she is willing to admit, accepting crumbs of affection seems worth it when the alternative, letting go of them completely, feels impossible. So many of Annie’s songs are a perfect encapsulation of how it feels to be twenty-something — the subtle self-sabotage when you know better, but can’t bring yourself to do better in the moment — and “Back In Town” is no exception. Ultimately, Annie pours out the feelings that she can’t share with her crush into this song, and we as listeners get to benefit from that, just like we do with the rest of her gorgeously raw and honest discography.
“California King” – Sincere Engineer
“California King” represents the other end of the spectrum from protecting your heart to embracing vulnerability. The lyrics of this song, written by frontwoman Deanna Belos, center around the fantasy of moving in with a partner. One of the first things you need to know about Sincere Engineer is how deeply rooted they are in the Chicago music scene. So when Deanna sings, “Maybe everything around me is too slow / Baby, in this city I’ve been feeling so alone / Lately I’ve been thinking ‘bout leaving Chicago,” it shows that she must really care about this person if she is considering leaving her beloved city to be with them. (Although I should note that nearly every time the band performs this song in Chicago, Deanna clarifies, “I don’t really want to leave Chicago.”) I love a good punk rock love song, and in my opinion, “California King” is one of the best. The fast-paced but soft guitars, combined with Deanna’s distinctive gruff vocals, create the perfect contrast to the sweet lyrics. The song beautifully encapsulates the overwhelming feeling that arises when you love someone so much you start daydreaming about intertwining your lives together.

Whether you’re in a mood to wallow in grief over a past situationship or fantasize about moving in with your new love, Annie DiRusso and Sincere Engineer have got you covered with their unconventional love songs. Of course, as someone who lives in Chicago and loves this city, I also appreciate the bonus connection that both of these songs include a Chicago mention. These two artists are incredible and on the rise – I definitely recommend checking out Sincere Engineer’s 2023 album Cheap Grills and Annie DiRusso’s Super Pedestrian that came out earlier this year.
