Enjolras (Les Miserables)
Tragically misunderstood by all the women–and most of the men–around him, Enjolras was both deeply beautiful and deeply loved. But he didn’t want to be loved like that. Because unlike just about any other boy you’ve ever met outside of a seminary, Enjolras was planning to die a virgin. If that doesn’t guarantee aloneness on the most romance-centric holiday of the year, well then, we just don’t know what does. Besides, nobody wants to talk about politics that badly.
Place you’re likely to find him: Sitting in Cafe Musain, angrily scribbling “No one cares about your lonely soul” over and over and over while staring at a map of the streets of Paris.
Mark Cohen (RENT)
Sorry to say, but the high holy days aren’t the only days Mr. Cohen can’t hold an erection. Between his intense commitment-phobia, his obsessive desire to document a world he kind of sucks at living in, and the scars from his breakup with Maureen, V-Day just isn’t Mark’s thing. So unless someone’s asked him to film their street-corner retelling of The Vagina Monologues through interpretive dance, Mark isn’t much likely to be out and about.
Where you’re likely to find him: In the cutting room, staring at the floor full of memories.
Archibald Craven (The Secret Garden)
P.O.O.R. Uncle Archie. He found love in a hopeless place, but it was torn away from him far too soon. Then, after years of seeing his dead wife’s ghost and waltzing around ballrooms with her in his mind (better than nothing, right?) he found actual happiness by loving his kid, and even her ghost peaced out. For reasons ranging from his weird physical deformity to his house’s total isolation, Archie isn’t exactly raking in the suitors these days.
Where you’re likely to find him: Lying like a starfish on the floor in the middle of the ballroom, thinking about oatcakes and cream and sweet plums in a jar, hoping his true love’s ghost will appear once more.
The Entire Cast of Into the Woods
Look. This is a Sondheim musical. Everyone is unhappy and at least vaguely fucked up about love. About human relationships in general, actually. In the case of the cast of Into the Woods, by the end of things, everyone has lost the person they loved — or thought they loved — most and The Baker is already in the process of fucking up the next generation. It’s looking grim. But hey. At least they’re not trapped in the sex dungeon, right?
Where you’re likely to find them: Sitting at the edge of the woods, thinking about their isolation and emotionally cutting by listening to “Being Alive.”
Claude Hooper Bukowski (Hair)
When you’ve proposed to your one true love, and instead of answering, she sings some song about starshine–that’s not even a word!–you start to feel a little bitter about romance. All the drugs Timothy Leary can buy aren’t enough to ease the pain of that kind of burn. Joining the military kind of seems like an honorable and reasonable way of escaping your misery at that point and frankly, Valentine’s day is no longer at the top of your mind.
Where you’re likely to find him: Standing outside the Military Induction center at 39 Whitehall Street, wishing Sheila had just said yes.
Mortiz Stiefel (Spring Awakening)
Moritz is such a conundrum. He’s single, but not because the girls aren’t interested. After all, he’s a sensitive dreamboat with rockstar hair. But somehow, he can’t just capitalize on romantic opportunity, no matter how hard he tries. We think some sessions with Dr. Drew and Zoloft would help ease the pain… and get him out of the house more often.
Where you’re likely to find him: Reading at home and ignoring phone calls.
John Wilkes Booth (Assassins)
He’s intelligent! He’s well dressed! He’s kind-of famous! And he kills people. And your most wide-eyed, optimistic American dreams. This literal life-ruiner likely didn’t have much time for romance as he was plotting the downfall of an American president. And that’s probably for the best.
Where you’re likely to find him: In the barn, watching the flames rise…
She’s lovely and loving and bohemian and wears clogs and has a cute kid and the vague insinuation of a sad past and she plays the piano in a haunting and deeply meaningful way and she writes sad, wise songs. Clearly, she’s every man’s dream. Except that she’s already been some other man’s dream and she’s so hung up on him that she can’t even figure out a way to make it work with Steve Kazee in a Henley. Now that’s a real tragedy.
Where you’re likely to find her: At home with her mom and kid, fussing with a vacuum cleaner.
Jud Fry (Oklahoma)
Poor Jud. Who, for the record, is not dead but occasionally wishes he was. Less dashing than his manly counterparts, kind of a loner, and obsessed with dirty pictures, Jud is a less than ideal Valentine’s Day date. Except maybe he was just before his time. Nowadays, he’d just ditch the prairie for Brooklyn, start a band, get some tattoos, grow a beard, and realize that Laurie was kind of boring and not his type anyway.
Where you’re likely to find him: Brooding in his shack with a stack of Playboys…
She might be literally green, but when it comes to poise and experience, she’s anything but. Elphaba doesn’t consider herself unlucky in love. She hooked Fiyero without much fuss, after all. But when it comes to enduring passion, Elphaba kind of can’t be bothered. She’s too busy being a political scapegoat, running the show, and making trouble for dim little girls. If you asked her about Valentine’s day, she’d likely respond with, “Sorry, pink is just not my color.”
Where you’re likely to find her: Plotting in the castle, surrounded by monkeys. Just the way she likes it.
Zach (A Chorus Line)
Before the world had Derek Wills, it had Zach – the brilliant, moody, pain-in-the-ass beyond the fourth wall in A Chorus Line. But really, the story of these two characters is the same. Obsessed with their art, a little disdainful of your status as a mere human, and forever hiding behind that bright light, they occasionally make pretty good musicals, but they don’t make great boyfriends.
Where you’re likely to find him: Blocking…