10 Songs About Heartbreak, Unrequited Love, and Getting the Last Laugh at the End of a Relationship that You Need to Hear


With summer just around the corner (depending on if you live in the Midwest or not), I know it’s technically that time of year when people are either beginning a new relationship or enjoying their singleness by just having a few casual flings. It’s also a great time for those windows down, feel good jams you blast from your car while cruising the town with your friends.

However, if there’s one thing I know about music fans, it’s that we all love and are total suckers for a good “cry in your beer” or “drink an entire bottle of wine while sobbing on the kitchen floor” type of sad song as well (no judgement here). Something about listening to someone sing about the pain and heartache of a bad breakup or unrequited love that really resonates with you and feels almost therapeutic. Sad songs are just good for the soul, and sometimes the soul needs to be fed like it’s Fat Tuesday.

So with that being said, I have compiled a list of 10 songs about heartbreak, unrequited love, and getting the last laugh at the end of a relationship that you didn’t even know you needed. Fair warning, though, the emotional wreckage that will come with listening to these songs is very real. Don’t say I didn’t warn you.

10) Madison Kozak – Graduation Day

Upbeat and full of sass, this snazzy tune is all about watching karma come back around to the person who deserves it because they “wrote the book on heartbreak school.” Hats off to Madison Kozak for getting the last laugh with a melody so catchy, you’ll be singing along while dancing in front of your mirror (again, no judgement).

9) Brinley Addington – Come Back

A traditional acoustic driven ballad about letting the one you love go so they can flourish on their own, all the while wishing and waiting for them to come back. Brinley Addington delivers an attractive vocal performance that’s filled with a hopeful pain that’s both heartbreaking and relatable as he croons the line, “I’ll leave the porch light on in case there’s something that you missed.” Excuse us while we wipe up the puddle we just cried.

8) Maddie Wilson – Rip

Maddie Wilson isn’t crying over the idiot who broke her heart. She’s too busy celebrating the breakup by going out in all black. As she says in the chorus, “So I’ll say R-I-P to your no-good love/And I can Rest In Peace knowing that we’re done/And I’m so over feeling like I ain’t good enough/So I’ll say R-I-P to your no good love.” A young Shania Twain in the making, Maddie Wilson is definitely one you will want to keep your eye on.

7) Delta Rae – One Good Cry

Soulful and tender, Delta Rae shine on one of their recent releases while showing off the latest music direction they’ve chosen to go in. Impeccable melodies sing of allowing yourself one last time to be vulnerable and give the one who broke your heart one last good cry. Needless to say, we can’t wait to hear what other new music Delta Rae has in store for us.

6) Lauren Jenkins – Running Out of Road

The ache Lauren Jenkins feels comes through loud and clear as she sings about not being able to escape the memory of her ex. With her raspy vocals that remind us of a young Stevie Nicks Or Bonnie Raitt, it’s damn near impossible not to feel haunted and completely wrecked by the emotion this rising star puts into her music.

5) Alana Springsteen – The Best Thing

You’ve never heard unrequited love sound as good as it does when Alana Springsteen is singing about it. Whimsical and dreamlike, “The Best Thing” is about wishing you could go back to specific moments with someone who isn’t yours. Springsteen’s melodies are incredibly sweet, and will leave you yearning for the one who got away, or as she puts it, “a dream you never wanna leave.”

4)Page Mackenzie – Love Like That

Powerhouse vocals and emotionally charged lyrics will leave you bawling in your wine glass as you listen to Mackenzie belt the line, “You found her/I found the bathroom floor/we had it all/but you wanted more.” Soaring to immeasurable heights vocally, it’s obvious there is nothing Page Mackenzie can’t do, and we look forward to what comes next from her.

3) Lady Antebellum – What If I Never Get Over You

Country music’s favorite trio is back and once again they’ve wrecked our hearts with their signature harmonies and emotionally crippling lyrics. This time around they pose one scary question – what if we never get over the one who broke our heart? Thanks for that Lady A. We’ll just be over here trying to focus on how fabulous this new song you dropped on us is instead of the emotional roller coaster you just put us on.

2) Honey County – Love Someone

Guy-wrenching and more relatable than we’d like to admit, Honey County’s “Love Someone” is unquestionably the modern day “Can’t Make You Love Me.” With irresistible harmonies that are comparable to no other group in country music currently, it’s safe to say that these three ladies will have a lot of success to look forward to.

1) Parker McKay – Honest

The most honest breakup ballad you will ever hear, Parker McKay will crush your heart and soul with her latest single. With lines like, “If I’m just being honest/I don’t care enough to get into it/And that’s a good indication of how we’re doing,” McKay perfectly describes the moment when you realize you just can’t make the relationship work anymore. To say we’re excited to hear what else McKay has up hr sleeve is clearly an understatement.


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"MADD" Manda Walsh
Chicago native and Saint Xavier University alum (class of 2007), Amanda Walsh is an aspiring journalist with a strong passion for music and longtime love of writing. While in college, she spent her time volunteering as a radio DJ, working as the station’s Music Director, and serving as a regular contributing writer for the campus newspaper where she combined her love for music and writing. Between attending multiple concerts a month all over the city, interviewing various bands both in and out of the studio, and introducing her friends and show listeners to new artists (both local and national acts), it was during this time that Amanda really discovered her niche. Whether listening alone with her headphones or experiencing it live in person, music has always been Amanda’s safe haven and more like a religion, with concerts feeling more like going to church. Today the number of artist interviews under her belt continues to grow, as she strives to break new and up and coming artists before other outlets. She also continues to attend as many concerts as her bank account will allow. Her musical tastes range from “OMG you have to hear this” to “please don’t judge me,” and she is the person you want on your team in music trivia. She is also an avid enthusiast of the paranormal and anything in the realm of horror or the creepy and unnerving. With that said, she loves Halloween more than a normal person probably should and has a fascination with cemeteries. Aside from music and concerts, Amanda also enjoys reading, shopping and epic adventures. She's a sucker for a good mystery and anything acoustic. When she was a kid she wanted to be Nancy Drew when she grew up. At the end of the day, if she had to describe herself with a song lyric it would be this – “I’m somewhere in between what is real and just a dream.”
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