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Sad-ass Valentine Day Songs

As far as good feeling love songs, my back catalog is sorely lacking. I just think it's easier and more pleasing to write ones of unrequited or broken love. Plus, when love is going good, the last thing I want to do is sit and write a song about it.

So, here are a few of my "hits"


Mexican Wrestler is probably my most requested songs and maybe the most sad-ass. What does this say about my fanbase? I like how the song starts off kinda funny, but then turns in the chorus - "You will never love me, and this I can't forgive. And it will always bug me as long as I will live..."



"I Put My Headphones On" is from Nostalgia Kills. And also is in "F*ck7thGrade - which you can stream now! The song celebrates the music I loved and listened to as a miserable kid. Yes, mostly the sad songs. This is from a live show at the City Winery with my band, "Dinah Shore Jr.".



"Now That I Don't Have You", I think might be my personal favorite. It's not as wordy as my usual fare. It gets straight to the point. And, it does have signs of hope. You get the feeling the singer (me) is not quite over a terrible breakup, but can see it coming.


Well, there are a ton more of sad-ass songs in my catalog. Check them all out!

And have a happy Valentine's Day!

© Jill Sobule