Valentine’s Day Music Videos: Our Favorite Songs of Romance and Regret

In the mood for love, or maybe for wallowing in sadness over a relationship gone wrong? Here are some songs that will help in either case.

Valentine’s Day is on its way, and we thought we’d help you get in the mood (regardless of whether you’re single or partnered up) with music videos for some of our favorite songs of love and heartbreak. Whether you’ve got a crush or you’re jaded on romance, there should be something here to fit how you’re feeling. Take a look—and let us know which of your favorites we left out.

Old 97’s - Question

“Someday somebody’s gonna ask you a question… A question that you should say yes to.”

True, this isn’t an official music video, but this is such a sweet song that we couldn’t pass it up. This gentle serenade about a proposal has been the soundtrack to many others—maybe you’ll want to use it for your own.
From the album Satellite Rides


Ben Folds and Western Australia Symphony Orchestra - The Luckiest

“I don’t get many things right the first time, in fact, I am told that a lot. Now I know all the wrong turns and stumbles and falls brought me here.”

One of the most beautiful love songs we’ve ever heard is enhanced by the soaring accompaniment of the Western Australia Symphony Orchestra.
The original version is available on Ben Folds’ phenomenal retrospective album.


The Civil Wars - Poison & Wine

“Your mouth is poison, your mouth is wine.”

A powerful anthem about loving someone despite the pain it causes you, voiced by the talented duo of John Paul White and Joy Williams from folk-rock group The Civil Wars.
From the album Barton Hollow


Bright Eyes - The First Day of My Life

“This is the first day of my life… I’m glad I didn’t die before I met you.”

One of the cheeriest songs from Conor Oberst (aka Bright Eyes) is also the best, in our opinion—and this heartfelt music video, that shows diverse couples sitting on a couch, listening to the song and cuddling, is destined to bring a smile to your own face.
From the album I’m Wide Awake It’s Morning


Ingrid Michaelson - The Way I Am

“I’d buy you Rogaine when you start losing all your hair… Sew on patches to all you tear.”

This music video, featuring a party full of clowns, shows the joy you find when you finally discover someone who’ll accept you for who you really are—whether you’ve got a big red nose or not.
From the album Girls and Boys


Jim James - A New Life

“Hey, open the door, I want a new life.”

Jim James, former singer of My Morning Jacket sings his heart out in this gorgeous plea to someone he loves to start a life together—made even better with backup music from The Roots.
From the album Regions of Light and Sound of God


Nina Simone - Feelin’ Good

“Birds flying high, you know how I feel… Sun in the sky, you know how I feel.”

Once those horns start in, it’s impossible to avoid this song’s lure. The incomparable Nina Simone shares the joy of a new love in this blues classic.
From the album Best of Nina Simone.