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An Aging Hipster’s Musical Guide to Valentine’s Day

Conor Oberst playing guitar live, singing with his eyes closed

What’s Valentine’s Day without music? No matter if you’re feeling in love, heartbroken or something in between, there are songs to accompany any feeling on this romantic holiday. While there are plenty of genres of music that could provide the perfect soundtrack for the celebration, us aging hipsters—aka emo before it meant eyeliner, Hot Topic and boy bands with guitars—have mastered the art of finding the right track to cover any emotion.

Trying To Make It Work (“Hope For Us”)

The Jealous Sound never made it big but their debut album, Kill Them With Kindness, was one to take notice of. Formed by former members of bands such as Knapsack and Jawbox, The Jealous Sound had a unique sound and the standout track from their debut album, “Hope For Us”, was old school emo at its finest. Heartbreaking lyrical content but with a passion that still exists, the line “Kiss me open mouth” in the chorus is bound to raise some eyebrows and inspire a few ideas, Valentine’s Day or not. A track that has stood the test of time, even if the band didn’t make it.

Is It Over? (“Options”)

Perhaps the most depressing song I’ve ever heard in my life is Pedro the Lion’s “Options”. The sound is slow and haunting; the lyrics tell a tale of a relationship in trouble and the need to keep options open, even the drastic ones. This is a track that while brilliant, can absolutely create a mood. It’s that powerful. Save this one for your most depressing of Valentine’s Days. That being said, damn I love Pedro the Lion. Kids these days don’t even know what real sad music sounds like.

Young Love (“I’ll Catch You”)

We all remember the teenage years, when every feeling, good, bad or indifferent was so intense. As teens, we’re nothing but pure emotion and passion in a sense. Feelings of love are so much more magnified and when teen love is going well, it feels like it’s going to last forever. The Get Up Kids “I’ll Catch You” is a perfect anthem for such feelings. The feeling that love can overcome all, that no matter what, “I’ll Catch You”, as Matt Pryor’s vocals illustrate is accented by their trademark James Dewees keyboards and building to a powerful full-band finale. Every emo or indie kid in this era wanted this song to be the one that played while they slow danced with the girl or boy that caught their eye. All these years later, this track still holds up.

Harsh Truths (“Tiny Vessels”)

“She is beautiful but she didn’t mean a thing to me”. One of the harshest lines ever sung and equally as surprising coming from Death Cab For Cutie frontman Ben Gibbard, who just didn’t seem like that harsh of a guy. “Tiny Vessels” was one of many great tracks on the band’s standout album, Transatlanticism, a song in which Gibbard wrestles with his emotions over not meaning the things he was telling a woman he was seeing. On some level, he wanted to believe what he was saying and he didn’t set out to use her for her looks but that’s what he ultimately did. While not relatable to everyone, for many of us, it is, and this kind of self-reflection isn’t a bad way to spend a Valentine’s Day. If we want to amend the behavior, we have to address it first.

First Date (“Hands Down”)

Dashboard Confessional, first and foremost, should always be acoustic. No offense to later fans but “Hands Down”, while more popular with the full band is 100x better acoustic, as Dashboard was intended to be. Now that I’m off my soapbox let us all agree that no matter how big and tough you might be, no matter how many pits you threw down in or how intimidating you might be, if you heard “Hands Down”, you turned into a lovesick puppy just like the rest of us. Chris Carrabba had a superhuman likeability to make us all want to go on first dates so cute that they could’ve been on an episode of Dawson’s Creek. Play this track this Valentine’s Day if you and your special someone want to feel cute or if you want to make a jaded heart ease up a bit.

Wanna Dance? (“The Deep South”)

The Promise Ring were a staple of the emo/indie rock scene and had an impressive range when it came to their sound. They could get as moody as anyone else in that era but also had a pop sensibility that was just downright fun. A song like “The Deep South” is just begging to be played in a scene from a movie where a couple lets loose and dances in their living room to the soundtrack of their younger days, loosing all inhabitations and embracing the moment. Maybe this Valentine’s Day, that could be you and your loved one, singing along with Davey Von Bohlen and dancing away to this classic.

Don’t Call Me In The Morning (“Lover I Don’t Have To Love”)

Ah, Bright Eyes, how I loved thee. Still do. “Lover I Don’t Have To Love” is haunting, sexy and a brutally honest depiction of the sex and drugs lifestyle, both means to fill a void. The song itself is seductive and could certainly be played to inspire a mood. The lyrics are heavy; while on face value could be inspiring to seek an erotic, yet emotionless sexual encounter are at its core a window inside Conor Oberst’s state of being at the time. How this song strikes you will likely depend on your mood at the time but to leave it off this list would be wrong. Easily one of my favorite songs from this era.

Broken Hearted Man Anthem (“Come Pick Me Up”)

Ryan Adams has had a fall from grace but for many years, “Come Pick Me Up” was the ultimate broken-hearted man anthem. From the moment you heard the harmonica that started the song, you knew this is going to be a sad one. There are lots of complicated feelings at the end of a relationship, especially one where you get cheated on and “Come Pick Me Up” from Adams’ debut solo record, Heartbreaker, puts those complicated feelings front and center. It’s not quite the Blues but its got a bluesy vibe to it and this song was a blast to sing along to, especially live. Probably won’t be doing that anymore though.

Moody…With a Twang (“The Death of Us”)

Matt Pryor has made the list twice! The Get Up Kids’ frontman had a side project called The New Amsterdams, which started off mainly acoustic and grew to feature a full band over time. The fourth album, which came out in 2006, featured “The Death of Us” as the opening track. It’s been said that the entire album, Story Like a Scar, was written while The Get Up Kids were experiencing their issues before their first breakup. “The Death of Us” is a haunting track, prominently featuring Pryor’s Kansas twang and as a songwriter, was some of Pryor’s greatest work. This is one where if you’re feeling down or moody at all this Valentine’s Day, should be an immediate go-to.

For The Lovers In The House (“I’ve Been Thinking”)

If you haven’t heard “I’ve Been Thinking” by Handsome Boy Modeling School (featuring Cat Power) before, stop reading right now and play the track. You’ll thank me in about five and a half minutes. Handsome Boy Modeling School and Cat Power seemed like a weird fit before I heard the song. Cat Power was an indie/folk queen and Dan The Automator was the greatest beat man in the game since Dr. Dre. The product of their collaboration was the sexiest song this side of Motown, and that’s said without exaggeration. This Valentine’s Day…you don’t need me to finish that thought.

What would have made your list? Let’s hear your cuts in the comments!

Written by Andrew Grevas

Andrew is the Founder / Editor in Chief of 25YL. He’s engaged with 2 sons, a staunch defender of the series finales for both Lost & The Sopranos and watched Twin Peaks at the age of 5 during its original run, which explains a lot about his personality.

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