Molly Ringwald: your former teenage crush

Molly Ringwald peruses the rack of designer clothing pulled in as potential attire for her imminent photoshoot, noting to the photographer that she’d prefer to avoid anything that might come off as being “too glamorous”. She immediately gravitates towards a lovely pink silk-shantung sweetheart-neckline number, reaching out to grab it.

“That one’s really pretty,” offers the stylist.

“But it’s pink,” murmurs Molly.

“Got it,” the stylist smiles.

“No pink for you these days?” I ask.

“I’ve kind of had enough pink in my life,” Molly deadpans, clacking the dress hanger down in the reject section without a second thought.

Everyone laughs, everyone gets it. That chapter has long since closed.

Many novelists might not mind an extra dose of glamour, and surely few would have such a knee-jerk aversion to the possibility of being portrayed in pink, especially if they’re pretty in it. But most other authors in question are not globally known first and foremost as actors, and not a single one of them at the very mention of their name will perpetually glide through the minds of millions as a sweet underdog teenager from the mid-1980s wearing a homemade prom dress that’s pink.

Molly Ringwald doesn’t shun the past, she just refuses to walk around in it. She happily obliges the legions who question her about the three classic coming-of-age films for which she’s best known – Sixteen Candles, The Breakfast Club and Pretty in Pink, all written by (and the first two directed by) the late great John Hughes. Ringwald recalls that watershed era fondly, and she has attended a few cast reunions, including a tribute to the departed Hughes at the 2010 Oscars. The bio line of Ringwald’s recently launched Twitter page even includes the rather apt designation “your former teenage crush”.

These days, the 44-year-old Ringwald is talking about her new collection of fiction, a “novel in stories” called When It Happens To You. We’ve spent the morning roaming around Venice, California, south of Ringwald’s home in Santa Monica and just north of Marina Del Rey, where her photoshoot will take place in the afternoon. A street carnival with rides and games is in full swing nearby as we breakfast at Venice’s Gjelina restaurant (she orders the Moroccan baked eggs with merguez), then wander the boutiques along trendy Abbot Kinney Boulevard, where Ringwald buys her kids a few gifts (some Japanese mugs with cute animal drawings on them).

Ringwald sparkles as she talks about her family, her work and her life. She’s genuinely inquisitive and constantly engaging. Conversations frequently veer off into music and books, two of the subjects closest to her heart (her father is jazz pianist Bob Ringwald). While she’s clearly focused on forging ahead, the woman who smiled out as a teen from the cover of a 1986 Time magazine next to the headline “Ain’t She Sweet?” finds that the past is never all that far behind.

“It’s heavy,” Ringwald admits, of walking around with an entire era on her shoulders. She laughs with a hint of frustration. “The more I pursue other things that really, truly matter to me, it’s less heavy, but I think the heaviest thing about it is that so many people have so many memories attached to me. It’s kind of like this giant collective unrequited love. I wasn’t there when they had their first slumber party or their first date or their first kiss, and yet I’m somehow connected to their lives in that way.”

A whole generation of teens saw their hopes and dreams in John Hughes’s us-against-them 80s high-school sagas, and if you weren’t actually there, at that perfect age at that perfect time, all you need to do is watch the films to get it. There was someone out there, someone creative, a story-teller, some guy in Hollywood… or at least somewhere, who freakin’ understood. Kicking against the cliques. And when the Allison character played by Ally Sheedy in The Breakfast Club opined: “When you grow up your heart dies,” that was my generation’s “Hope I die before I get old.” It stuck. So having literally played a part – or rather parts – in all of that, Ringwald has understandably been a magnet for much of the residual sentiment.

“I was obviously very different from those characters,” says Ringwald. “I’d been acting professionally since I was a child; I was pretty well travelled and a lot more urban. Most of those characters were in small suburban towns outside of Chicago, really sort of more representative of a certain type of girl in the United States at a certain moment. Not necessarily representative of me. In those films I was sort of the ‘everygirl’, I guess.”

So what’s it like to continue to exist as so many people’s perpetual everygirl?

“Sometimes it feels extraordinary and moving,” she says. “Depending on the day, it can be really sweet and nice and then other times it feels like: ‘Arrrrrgh!’ But I just joined Twitter and I’ve had this connection to fans that I’ve never had before – it’s been really amazing. There are some really cool people who have followed me for years, but then there are a lot of people who are just absolutely clueless that I’ve continued to grow and evolve and be someone else. They’re very focused on those particular movies. And you know, I can’t blame them. I’ve never done anything else that’s had that kind of an impact.

“And it’s really gone into different generations,” she marvels. “I always kind of liken it to Catcher in the Rye, because it was written in the early 50s, and I remember reading it in the 80s – actually when I was doing those movies – and thinking that it was written just for me – you know, relating to it so intensely. I think those movies have the same effect.”

She understands this impact, and can indulge it. “There was a whole Twitter war going on recently because I said I think the Duckie character in Pretty in Pink is gay,” Ringwald laughs. “It freaked a lot of people out, but in a way I feel like John Hughes was writing a lot of gay archetypes. But at that time it really wasn’t sort of acceptable – you know, a character in high school couldn’t just be gay. But I mean, c’mon… the way that Duckie treats me, he’s written totally as the gay best friend – there’s no sexual chemistry between us!”

And Ringwald doesn’t mind speculating on what perhaps eventually became of her own characters. “I’m a born optimist, but I imagine that Claire from The Breakfast Club probably went through a few husbands,” she laughs. “I think Andie from Pretty in Pink probably got the best education and Samantha Baker from Sixteen Candles probably sort of stayed where she was, but it’s up to the viewer to decide all that. I do like to think that it all worked out pretty well for all those characters.”

Ringwald continues to act – in film, on stage and on television. For the past five years she’s been a regular on the ABC Family channel’s The Secret Life of the American Teenager, and no, she does not play one of said teenagers with said secret lives; she now, of course, plays a mum. Who recently came out as a lesbian.

She’s also a well-seasoned singer. Incredibly seasoned, in fact, as she put out her first album, I Wanna Be Loved By You: Molly Sings, at the age of six. And she’s a mother, not just on TV – she has an eight-year-old daughter and three-year-old twins, a boy and a girl.

But today she is wearing her writer’s hat. Literature, she says, has informed her performance throughout her career. She’s a voracious reader, she has written numerous articles (including a moving op-ed piece for the New York Times when director John Hughes died three years ago) and she even met her writer/editor husband, Panio Gianopoulos, while discussing books with mutual friends in something of an online literary salon. (He posted a John Cheever quote, she posted lyrics from one of her favourite bands, the Magnetic Fields, and the rest is history.)

Now Ringwald is proud to be ruminating upon When It Happens To You. It’s actually her second book, as the 2010 Getting the Pretty Back: Friendship, Family and Finding the Perfect Lipstick was her debut. But while that was a non- fictional mix of personal anecdotes, recipes, relationship advice and fashion tips aimed at middle-aged women, the eight interlocking stories in When It Happens To You resonate much closer to her heart and her intellectual sensibilities.

“They’re very different. When I had the idea to do Getting the Pretty Back I sort of viewed it as an object. I saw it in my head as illustrated and beautiful, and it really had to do with me turning 40 and realising that there were no books, it seemed, about stylish women. They were all about girls. So it was very connected to my life as a public person, like writing a book for my fans who have been there all these years.”

When It Happens To You explores deeper and darker themes, such as struggling to recover from the crash and burn of drug abuse, and negotiating the emotional terrain of raising a transgendered child.

“It’s really like the difference between me as an actress and me as a writer,” Ringwald muses. “My husband likes to say that my first book was a bit like sticking my toe in the water, doing something that was still very connected to my acting. This one’s much closer to my sensibilities as a writer and what I’m more interested in, even in terms of what kind of movie I want to see or what kind of part I want to play. The only kind of character I’m really interested in playing is somebody who is flawed. And all of the characters in this book are so deeply flawed.”

When It Happens To You unfurls like a ripped-up tapestry of lost souls, a puzzle-like pictorial to be woven together by the reader as the denizens of the eight separate stories collapse in and out of each other’s lives. It’s a rather dark book but a good read; even the title is somewhat ominous.

“I really wanted to write a book about betrayal. That was the original idea. I wanted to think about: ‘What are the things that connect us? What connects humanity the most?’ Not to get all heavy or anything…

“I thought: ‘What about betrayal?’ Everybody is always betraying somebody; everybody has either betrayed or been betrayed or has betrayed themselves. So there’s this theme that weaves through the whole thing, and I think it’s something that’s very relatable for a lot of people.

“I don’t find it bleak. I just think every character is struggling with a mess that they’ve made of their life and muddling through and finding their way out of it. You know that song by the Talking Heads that goes: ‘And you may ask yourself… how did I get here?’ I had that in my head a lot while writing this book.”

Conversations with Ringwald frequently stray into the territory of song. In writing When It Happens To You, she created individual playlists for each of her characters – and while most people’s flashback mental soundtrack for Ringwald herself will forever be the Psychedelic Furs, Simple Minds and Orchestral Manoeuvres in the Dark, her own first love was jazz, thanks to her father. She began singing with his group, the Fulton Street Jazz Band, when she was just a tot.

Early next year she’s releasing a new collection of jazz standards (plus a song she wrote herself with her pianist), and she plans to tour with her band next February.

“I’ve never been the kind of person who just wants to surround myself with actors and acting,” Ringwald explains of her non-Hollywood interests and acquaintances. “I know very few actors personally, other than the ones I’ve worked with. I’ve always gravitated towards either writers or musicians.”

Even back in the 80s, the now-legendary “Brat Pack” moniker was a total misnomer when it came to Ringwald’s inclusion. The term came from a lengthy 1985 New York magazine article about the likes of Emilio Estevez, Rob Lowe and Judd Nelson cavorting around Hollywood spending piles of cash and picking up girls. “I wasn’t even part of the article!” Ringwald cries. “Isn’t that crazy? But I somehow became the ‘women’s auxiliary’. Emilio and Rob and Judd out being 20-somethings, you know – it was ridiculous!”

“The best part of those movies for me was just making those movies,” says Ringwald. “That it was me who was chosen by John Hughes, that I was the one who inspired him, you know? I think that’s incredible and I’m proud of that. All that is just coming into my eight-year-old daughter’s consciousness, and I’m really excited for her to discover those films. I’m honoured and flattered that I mean so much to people. It’s a part of me, just like everybody’s teen years are a part of them, but they don’t live there every day, and I’m no different. Other than the fact that I’m sort of a cultural icon.” She laughs. “Y’know, I guess not everybody can say that.”

When It Happens To You: a Novel in Stories is published by Simon & Schuster today at £10. To order a copy for £7.50, with free UK p&p, go to guardian.co.uk/bookshop