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Valentine’s Day on Broadway: An Anti-Love Song Playlist

Category Broadway

|by Mark Robinson |

Because Broadway’s anti-love songs can be even better than its love songs

Valentine’s Day is a blissfully hypnotic holiday, full of public displays of affection for those who are in love. Then, there is the rest of us, whose Feb. 14 plans are far less exciting. If your Valentine’s Day looking a little different from the candy and card fest that others expect, here’s a musical theater song compilation for those who won’t be humming the love songs of Broadway. Without further ado, we proudly present: The Anti-Love Song Broadway Playlist.  

Lauren Ambrose and Diana Riggs in ‘My Fair Lady’ (Photo: Joan Marcus)

Lauren Ambrose and Diana Riggs in ‘My Fair Lady’ (Photo: Joan Marcus)

“There’s a Fine, Fine Line” from Avenue Q

Have you ever felt like a puppet in a relationship, like someone else is calling all the shots? If not, just ask Kate Monster of Avenue Q, who speaks firsthand from a puppet perspective in the song “There’s a Fine, Fine Line” by Jeff Marx and Robert Lopez. Coming to terms with the ambiguity shown to her by Princeton, the puppet of her affection, she ruminates about that blurred area between “love and a waste of your time.”

“I’m Not That Girl” from Wicked

We all know what it is like to be spurned by the one we love when, instead of thinking with their brains, they follow other instincts. At least that is how Elphaba feels in the musical Wicked when she believes Fiyero prefers the bubble-headed Glinda over her. The Stephen Schwartz song “I’m Not That Girl” sums up how we can feel as though we don’t measure up in such a scenario. 

“Love Look Away” from Flower Drum Song

It’s can be cathartic – though not necessarily healthy – to perpetually wallow in our misery over a love that is not reciprocated. If you want to get really depressed over unrequited love, look no further than Rodgers and Hammerstein’s “Love Look Away” from the musical Flower Drum Song. This hauntingly beautiful song will having you hugging your pillow and ingesting a gallon of ice cream in no time. (It may also remind you why single-serving pints are a joke.) 

“I Hate Men” from Kiss Me, Kate!

We know that most men aren’t horrible, but the sexist, self-centered and cocky had better beware when Katarina from Kiss Me, Kate unleashes her waspish distaste for the male of her species. Careful, you might find that this Shakespearean shrew clubs you with a turkey leg, or crowns you with a tankard of wine, as she details your shortcomings in the Cole Porter ditty “I Hate Men.”  

“Without You” from My Fair Lady

What feels better than telling off someone we’ve lavished our time and energy on, but who acts like they are the only person of value in the relationship? We practically jump out of our seats when Eliza Doolittle rips into Henry Higgins in My Fair Lady for his egotistical, self-absorbed ways. The Lerner and Loewe song “Without You” drips with delicious revenge and spiteful rhetoric, practically an anti-Valentine’s day poem just begging to be printed in a Hallmark card. 

“Not a Day Goes By” from Merrily We Roll Along

Stephen Sondheim gets the ache of being misused by someone we love, or at least gives a pretty good impression of it in the haunting “Not a Day Goes By” from Merrily We Roll Along. Haven’t we, at some point “died day-after-day-after-day-after-day” with the slow hurt that comes with a relationship crumbling apart? Since this song is sung on the steps of a courthouse following divorce proceedings, think of it as the perfect build-up to asking for alimony.

“The Gentleman is a Dope” from Allegro

Have you ever been in love with a truly wonderful person who, instead of acknowledging your own devotional attributes, would rather lavish their time and affection on someone who treats them like crap? That is the essence of the Rodgers and Hammerstein song “The Gentleman is a Dope” from the 1947 musical Allegro.  We all try to “fix” people and hope they will thank us for it, and that is exactly what this song describes. 

“Tango: Maureen” from Rent

Two people vying for the same heart makes for an uncomfortable and soul-crushing love triangle. Mark and Joanne both love Maureen in Rent, but it seems as though neither of them are destined for a functional relationship with her in the Jonathan Larson song “Tango Maureen.” Get a canary; it is easier and infinitely less complicated.

“To Keep My Love Alive” from A Connecticut Yankee

Love affairs can end badly. So can marriages, as is detailed by Morgan Le Fay in the musical A Connecticut Yankee. The sparkling Rodgers and Hart ditty “To Keep My Love Alive” (one of the last songs this duo would write together) is a loving account of all of Le Fay’s former husbands, their annoying quirks, and the clever ways she has murdered each of them. Nothing says “anti-love” better than a mounting death toll of former lovers.

“I Wish I Were In Love Again” from Babes in Arms

What is the point of love, anyway? It can really just lead to a list of aggravations that outweigh the companionship. In the Rodgers and Hart song “I Wish I Were In Love Again” from Babes and Arms, we can see the mounting frustrations that come with sharing your heart with someone special. In the end, however, I suppose we all would prefer to endure the struggle, even at the cost of our sanity. But then, where love is concerned, is there really anything sane about it? 

Mark Robinson is the author of the two-volume encyclopedia The World of Musicals, The Disney Song Encyclopedia, and The Encyclopedia of Television Theme Songs. He maintains a theater and entertainment blog at

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