I wore his shirt – crisp and fresh from the laundry basket as I hung my own rain-soaked clothes to dry.  The conversation was sparse but the air was gravid with an intangible emotion.  By the end of the day, we had not touched once and he saw me off at the door, wearing my own clothes again.

He was merely an acquaintance but years after that moment he still represents the most romantic day of my life.  Those who know me know that I have trouble accepting traditional notions of romance and the labeling of anything as “romantic” is kind of a big deal for me.  Guys I’ve dated can tell you that I have wrinkled my nose at their many attempts to be romantic.  Guys I’ve dated can also tell you that my response to the first “I love you” is usually shoving something in my mouth that takes a really long time to chew.  It’s something that I’ve always felt really bad about – especially as a writer.  Falling in love is such a common theme in storytelling that the Anti-Romantic can really feel left out.

Over coffee with a friend earlier this week, we discussed the impracticality and inconvenience of falling in love.  Science has found falling in love akin to mental illness so… yikes – what do I need that for? My friend and I conceded to the fact that like any common virus, lovesickness will find its way to us one day regardless of how ready we are for it.  He added that the only thing we really have to fear regarding falling in love is if it were unrequited.  Naturally, I thought back to that acquaintance from years before.  I admit that the mention of his name today still makes my heart do something that it doesn’t do at the mention of any guy I’ve actually dated and loved somewhat.

Branding a moment of unrequited love as “The Most Romantic Moment of My Life” is kind of masochistic (masochism! This is something I can share with my fellow writers if not the act of falling in love).  Unrequited love wins in the romance department because it has no conclusion.  Since neither party acted on these often unspoken feelings, the mind is left to wonder what could have happened or what can happen still.  The angst and emotion coupled with the repression and sexual tension that comes with unrequited love can prove to be a great tool for the storyteller.  While reciprocated love can be as intense and emotional, it lacks the conflict that exists in the unreciprocated.  As Jim and Pam have proven, requited love just isn’t nearly as interesting – some things should just be left to fan fiction.

I polled some friends on their favorite instances of unrequited love in fiction.  Below are the fifteen couples I’ve selected from their suggestions in no particular order:

1. Charlie Brown and the Red-Headed Girl of Peanuts – “Nothing spoils the taste of peanut butter like unrequited love,” says Charlie Brown.  The sentiment is shared by many – and naturally so.  A friend of mine adds, “The only thing that stopped Charlie Brown was his own insecurity, which appeals to a lot of young guys even 50 years later.”

2. Mrs. Chan and Mr. Chow of In the Mood for Love – I’m going to ruin the classiness of this movie by calling Mrs. Chan and Mr. Chow one of the most blue-balling relationships to ever exist in film history.  I’m glad Mr. Chow gets to blow off some steam in 2046.

3.    Angela and Brian of My So-Called Life – Oh that archetype of the neutered boy next door and his hapless crush on some girl too focused on high school angst to recognize that this guy “just gets her.”  Though I’ve never watched the show, my friends say that Brian pulls a Cyrano de Bergerac type of thing towards the end of the series (thus, revealing his true feelings) right before the show gets sacked.  Way to leave ‘em hangin’.

4.   Basically Everyone in A Midsummer Night’s Dream – Man, what a messy situation – as if love weren’t complicated enough on its own, all these fairies come in with mind-altering spells and potions and whatnot.  What are you to do when you literally fall for an ass?

5.    Pip and Estella of Great Expectations – If I had to deal with unrequited love, a book of this length is the last place I’d like to deal with it.  Julia tells me that Dickens was pressured into putting the two together at the end “but nonetheless poor Pip spends the entire book just piiiining away for her.”

6.    Daria and Trent of Daria – Everytime Daria visited Jane at home, my heart pounded just a bit harder when she passed Trent’s room.  Like Mystic Spiral, Daria and Trent’s relationship never really took off although Daria went on to steal Jane’s boyfriend, Tom.  She did quite well despite her misfit nature…

Lloyd Weber's Version of Leroux's Tale

7. Erik and Christine of Le Fantôme de l’Opéra – Imagine people being murdered left and right at your workplace because you didn’t love that weird guy who lives in the basement as much as he loves you.  How selfish of you, Christine – love the guy back or your colleagues are gonna keep dying!

You realize they only go undercover to satisfy viewer fantasies without compromising their relationship, right?

8.  Benson and Stabler of Law and Order: Special Victims Unit – I put this in here for a certain someone from Lit Drift that likes this show quite a bit.  If she’s anything like me, she watches this show hoping that Benson and Stabler will partner up in something other than crime solving.  Nudge nudge – wink wink.

This episode makes me sob... as do quite a few others...

9.    Fry and Leela in Futurama – My personal favorite of the bunch.  Fry’s love for Leela is almost childlike in its simplicity and his attempts to get her attention and gain her love are as clearly depicted in the series as it is on the holophonor. It should also be noted that Fry and Leela fan-edited YouTube videos are the only ones of that sort that I can tolerate.

10.    Florentino and Fermina of Love in the Time of Cholera – Can a man who sleeps with over 600 women retain the ability to single out and love one person so intensely? This pair popped up quite a few times among my friends’ suggestions so that must say something about how great of an example of unrequited love it is… oh, and the answer to that first question is yes because “he remained a virgin for her.”

11.    Daniel and Lindsay of Freaks and Geeks – I suspect if the show wasn’t canceled, these two would have ended up together and previously disgruntled fans all over the world would rejoice in the Franco-Cardellini goodness.  Runner-up pair in this show would definitely be Neil for Lindsay.

12.    Jim and Pam in the first three seasons of The Office – I know I knocked them earlier in the post but not mentioning them in this list would be blasphemous in the world of unrequited love.  Though Fry and Leela may be my favorite, Jim and Pam are the most realistically portrayed with poignant split-second moments that make you go, “ARRGGGGHHHHH” inside.

13.   Don Quixote and Aldonza of Don Quixote – The man was crazy and the gal was a whore but his blind and somewhat undeserved love for her was needed when she was so unable to provide it for herself.  Through persistence, Don Quixote was able to convince Aldonza to be the Dulcinea he had always believed her to be.

14. Tom and Summer of (500) Days of Summer – What’s worse? Not having the one you love or kind of, sort of but not really having someone? Though Tom and Summer were basically together and yay! – Tom gets to sleep with Summer – he doesn’t really have her.  You know what I mean? Oh those effin’ quirky, free-spirited girls.

15.  Dorian and Sibyl in The Picture of Dorian Gray – A friend and I came to the conclusion that determining your “league” lies in not only your physical appearance but also your talent.  Though Dorian was the first to profess his love, he later rejects Sibyl when her love is reciprocated (so much so that it destroys her acting career) citing the fact that her beauty stemmed mainly from her talent as an actress.  Harsh.

I understand that there are dozens upon dozens of examples that I have not listed.  Some runner-ups from my friends’ suggestions include a whole bunch of people from Battlestar Galactica, some Victor Hugo characters, and Bella and Jacob from Twilight.

If you think there are notable ones that should be mentioned, by all means – add them on! Comments are totally welcome… hell, share your personal stories of unrequited love if you’d like to.