Valentine’s Day is like herpes: just when you think it’s gone for good, it rears its ugly head once more. For all my single ladies out there, in light of this dreaded holiday that approaches, I have put together a list of heartbreaking songs that will make you feel so damn depressed, you will simply binge drink while eating your feelings until you eventually pass out and wake up to February 15th having forgotten the day before even happened.


Before you chase a bottle of Excedrin with a bottle of Jack, just remember that which doesn’t kill us, makes us stronger! Enjoy!




Ranked at #331 on the Rolling Stone magazine’s list of The 500 Greatest Songs of All Time, “I Can’t Make You Love Me” was written by Mike Reid (born and raised 30 minutes from my hometown in Altoona, Pennsylvania) and Allen Shamblin. The idea for the song came to Reid while reading an article about a man arrested for getting drunk and shooting at his girlfriend’s car (again, he was born and raised in Pennsyltucky). The judge asked him if he had learned anything, to which he replied, “I learned, Your Honor, that you can’t make a woman love you if she don’t.” How articulate, the poet Laurente of Dogwood Lane.


For many of you, it should be no surprise that this song can be found at the top of my list. When it comes to sad and depressing songs this one is right up there with Amazing Grace. Usually Mister Kitty and I like to warm up one our favorite Lean Cuisines, retire to our bedroom where we slip into something more comfortable, find our fire engine red MAC lipstick from MAM 2008 and put on some Bonnie Raitt until the tears put us to sleep.
mp3 download: Bonnie Raitt – I Can’t Make You Love Me

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This tear jerker by Des’ree was featured in Baz Luhrmann’s 1996 remake of the famous Shakespearean play Romeo & Juliet. “Two households both alike in dignity, in fair Verona where we lay our scene. From forth the fatal loins of these two foes, a pair of star-cross’d lovers take their life.”


Honestly, can you imagine a more tragic twist of fate than falling in love with the one person you’re not allowed to have? This song has to make you feel some small amount of sympathy for pedophiles…or at least for Gayle King.
mp3 download: Des’ree – Kissing You

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From A Fine Frenzy’s the One Cell in the Sea album, “Near to You” is by far my favorite sad songs. “Almost Lover” certainly received more attention and praise; however, I think the message in “Near to You” is an important one. Take a listen and then call me…we’ll discuss over a box of wine and pack of ultra lights.
mp3 download: A Fine Frenzy – Near to You

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Ohhhhhh gurrrllll…this song is gonna make you want to go STRAIGHT DOWN THE PARKWAY. No pathetic attemps for attention by crossing the freeway with this one! Right after The Outfield’s “Your Love”, I want this song played at my funeral. Give me one reason not to like this song…and I’ll turn it back around. Let’s face it, when it comes to suffering, Black, angry, Baptist lesbian’s are right up there with Elizabeth Taylor.
mp3 download: Tracy Chapman – The Promise

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Speaking of Lesbians…hold on to your Birkenstocks Lilith Fair lovers!! Known for her emotional ballads and mezzo-soprano vocal range, this Canadian mother of two has brought us so many “slow jams” in her short, yet successful career. Do What You Have to Do in my opinion is the best song from her 1997 album, Surfacing. Unfortunately it was lost among so many other hits from the album such as “Building a Mystery”, “Adia” and “Angel”.
mp3 download: Sarah McLachlan – Do What You Have to Do

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You know you’ve made it when the Emmy award winning Mia Michaels from So You Think You Can Dance chooses your song for one of her choreographed lyrical pieces. We all heard “Love Song” so many times it made us just want to punch a puppy, but “Gravity”, from her debut major-label album Little Voice, is such a beautiful song with so much meaning. Sara claimed the song is about a break-up. I’ll spare you my boring personal interpretation of the song; just take a listen for yourself.
mp3 download: Sara Bareilles – Gravity

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Who can forget the last scene of HBO’s Six Feet Under, as Claire drives off in her Prius and “Breathe Me” is playing the background. Girl, I had to take to the bed after I heard this one. Talk about a song! Do yourself a favor and find the Mylo Remix of this one. What can be better than a sad depressing song turned into a gay club dance mix?
mp3 download: Sia – Breathe Me

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With the huge storm we had, traveling to New York for fashion week, and a trip to San Fran this weekend I haven’t had much time to update C&B. So a big thank you to Mikey for guest posting this week. And for those who are single on Valentine’s Day, a lot can happen in a year, so here’s hoping these songs will be a distant memory come February 14th, 2011.

Tags: A Fine Frenzy, Bonnie Raitt, Des'ree, Sara Bareilles, Sarah McLachlan, Sia, Tracy Chapman