Trying to figure out the right songs to send your crush without making things weird? This week, I’m building a not-at-all-awkward soft-launching playlist — the kind of mix that lets you test the waters, drop a hint, but keep everything fun, flirty, and totally low-pressure.

These are the songs that say “I kinda like you” without turning it into a grand gesture. No heavy power ballads. No dramatic declarations. Just genuine tracks with the right vibe — warm, charming, and subtle enough to send with confidence.

I’ll dig into why certain songs land better than others, how the right track can quietly move a connection forward, and what actually makes a crush playlist work. So if you’re looking for the perfect “hey, I’m into you” starter kit as we roll toward Valentine’s Day… let this episode be your guide.

Thanks to Mixtaper Bryan Rosenberg for sending in this week’s playlist concept.

Fun fact: that’s my actual beeper from high school in the episode artwork. 🤷🏼‍♂️

🎙️ Subscribe now on Apple Podcasts, Spotify, or your favorite podcast platform—and don’t forget to leave a 5-star review to help more music fans find the show! Then, scroll down to hear all of the songs discussed in this episode. 👇

The Cranberries – Dreams

Foo Fighters – Big Me

Jack Johnson – Better Together

Bruno Mars – Just The Way You Are

Uncle Kracker – Smile

George Strait – Check Yes Or No

Butch Walker – You Belong With Me

The Proclaimers – I’m Gonna Be (500 Miles)

Tal Bachman – She’s So High

Sixpence None The Richer – Kiss Me