Contributor Picks: Heartbreak

The most fascinating tradition associated with Valentine’s Day comes the weekend after, when scores of men and women who’ve long given up on their relationship finally break the news to their significant other. In their minds, the dumpers have done their former mates a favour by not leaving them on a lurch on this commercial of holidays. However, if you’re the dumpee, it’s hard not to feel like you’ve just wasted a small fortune trying to rekindle a flame your ex had already doused with salted water. As such, we dedicate these four recommendations about heartbreak to all the newly broke dumpees of the season.

Chris’ Pick:
What I Loved (2003)

For years, one work has stood out for me as the ultimate example of the slow motion train crash that is heartbreak. I’m referring to What I Loved by Siri Hustvedt. Published in 2003, the novel follows the lives of Leo Hertzberg and Bill Wechsler, an art historian and an up-and-coming artist respectively, as they befriend each other in nineteen-seventies New York and then get kicked in the groin by love, loss, longing, and mental illness. At the time, the book so wrecked me that I went out and convinced at least three of my friends to read it, hoping to find refuge from my grief in their own.

I’ve since avoided What I Loved at all costs, especially now that I’m a father. In fact, I think I may have purposely lost my copy of it during a move, although one of my routine Audible and iTunes searches is for exactly this novel in audio form. Like my sadly mistimed project to listen to The Road a few Christmases ago, the thought of having this story read to me for hours at a time seems like the perfect antidote for certain moods. Voice actors, take note: you’ll have at least one guaranteed sale.

Nick’s Pick:
The Wedding Singer (1998)

There aren’t too many video games about breakups, or even love unless you count the Leisure Suit Larry series, so I’m going to take a shot at talking up one of my favourite movies: The Wedding Singer. Adam Sandler stars as Robbie (Adam Sandler), the titular wedding singer, whose heart gets broken after his fiancée Linda (Angela Featherstone) leaves him at the altar. New love and a chance at healing come when he befriends Julia (Drew Barrymore), a new waitress at the reception hall where he works. Unfortunately, she’s engaged to Glenn (Matthew Glave), who proves less than faithful. Hilarity ensues.

I was dubious when my friends recommended The Wedding Singer to me. After catching parts of Billy Madison (1995) and Happy Gilmore (1996), I’d come to the conclusion that Adam Sandler was insufferable. However, this film shows he can deliver a solid comedic performance without coming off obnoxious, owing largely to his chemistry with Drew Barrymore. What’s more, the movie takes place in the eighties, which means lots of hilarious pop culture references and a great soundtrack from the best musical decade ever!

Pamela’s Pick:
Sliding Doors (1998)

Whenever my heart gets broken, my go-to movie is Peter Howitt’s Sliding Doors, which, like Notting Hill (1999), offers the perfect remedy to having an afternoon to oneself but not enough brainpower to focus on anything of substance. The story opens with Helen (Gwyneth Paltrow) losing her job and then missing her train. From there, it splits into two plotlines: the original one, in which she goes about her day unaware that her boyfriend (John Lynch) is cheating on her, and a parallel universe thread, in which she gets through the titular sliding doors and catches her cheating beau in the act. In both storylines, our heroine gets hurt, gets angry, and gets even in varying ways, but she ultimately finds her path and fated love (John Hannah) one way or the other.

Sliding Doors suits my mood in times of malaise for the following reasons in no particular order: because the romantic comedy is distressing enough to cause in me the cathartic tears that serve as my first step toward feeling better; because Helen finds her true love in the end, and that fills my heart every time; and because the premise itself provides me with comfort. Sometimes, the doors are supposed to close, and we’re meant to miss the train because, when all is said and done, we always end up right where we we’re fated to be, making every hardship and frustration worth it.

Get Over It exemplifies the guilty pleasure. Here is a dumb teen comedy about dumb teen characters enacting dumb teen clichés while making dumb references to Midsummer Night’s Dream of all things. High school senior Berke (Ben Foster), our notional Lysander except not really, has just got dumped by Allison (Melissa Sagemiller). He needs to, you may have guessed, get over it. Instead, he tries to win her back by auditioning for the school play, a musical production of the aforementioned Shakespeare classic. As these things go, he there meets his nemesis, boy band diva Bentley (Shane West), and the true love of his next four months, Kelly (Kirsten Dunst). I’ll let you figure out who ends up with a donkey head.

The genius (you read that right) of Get Over It lies in director Tommy O’Havers ramping up the inanity with knowing, self-deprecating charm. Consider the opening lines of the Midsummer Night’s Dream musical, which pays off a running gag about its writer-director’s (Martin Short) flamboyant incompetence: “Did you ever hear a Shakespeare play and never understand a word they say?” Simply put, the movie bursts with satirical wit and joyful exuberance. These may seem like odd qualifiers for a recommendation about heartbreak, but I firmly believe the greatest cure for any soulful ailment is a healthy dose of irreverence.