Time After Time by Cyndi Lauper
This is one of Cyndi Lauper’s biggest hits. When you hear it, you think of all those missed moments you could have said what you wanted, but didn’t. You wonder: What if?
Your Song by Elton John
This sad song is so simple that it touches on anyone you ever loved that didn’t love you back or you haven’t met yet.
True Colors by Cyndi Lauper
If you’re hiding something or want to be accepted for who you are, grab the napkins.
True by Spandau Ballet
No one ever really got what this sad song meant. The verses are quite cryptic but can mean anything. It has a nostalgic feel of better times of innocence and coming of age.
I Can’t Tell You Why by The Eagles
If you had a relationship that you tried over and over again to fix, and you both gave it a good go, but still nothing, these lyrics will speak to you. We really do “make it harder than it has to be.” It’s all about loyalty, and sometimes, loyalty does not always mean happiness.
Dance With My Father by Luther Vandross
Rarely do we hear songs about parents. Pull up to this and think about the ones who made you. They feel pain too.
Against All Odds by Phil Collins
A moving sad song about what could have been, and what it feels like to experience loss…and waiting.
Old Lang Syne
This classic New Year’s Eve tune never fails. Another nostalgia piece, it takes you back to every loved one who passed away. It’s like seeing their faces on a slide.
Fast Car by Tracy Chapman
There are times where we want to give up and disappear. No frills, no expensive ticket to travel the world, we just want to go–anywhere. Ms. Chapman tapped into a deep sense of freedom we all wish to experience: to be who we are with who we want.
All of Me by John Legend
This is a good play when you’ve messed up. Think about the unconditional love you share, or used to share.
They’ll Be Sad Songs by Billy Ocean
This is a sad song about sad songs. A must-listen in between boxes of tissues.
Someone Like You by Adele
Yup, most of us are with second best. The guy or girl who wasn’t our top pick. This song is for those times you think about #1.
When I Was Your Man by Bruno Mars
If you missed an opportunity to get it right, Bruno reminds you that you’re not alone!
Stay by Rihanna
Ever felt completely vulnerable and exposed in a relationship? This song hits on all the points of why some people choose to never leave.
Youth by Daughter
The words alone without the music will bring tears to your eyes. Definitely reserved for the “ugly cry” moments. A haunting, beautiful song.
Wakeup Alone by Amy Winehouse
The lyrics to this are dark and passionate. The title itself says it all when it comes to the pain of loneliness.
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