In the flickering candlelight, it was clear to the other diners at the exclusive Blue Hill restaurant in New York that the couple at the corner table was in love. They had arrived in the bustling city the day before, a brief break in their hectic work schedules to celebrate his 41st birthday. And it was there, at that corner table, on that Friday in early August, one of the most enduring media sagas of this century drew to a close, when actor Justin Theroux presented Jennifer Aniston, his girlfriend of just more than a year, with an eight-carat, emerald-cut diamond engagement ring.

It’s the fairytale ending we’ve so desperately wanted for the actress, ever since her real-life Hollywood romance with Brad Pitt came so publicly, and painfully, crashing down in 2005. Her divorce became a humiliating global spectacle (“The split heard around the world,” as Us Weekly put it) that saw Aniston become the globe’s most famous, and publicly tormented, singleton. For the woman who had launched a thousand haircuts, it was a bizarre reversal of fortune. Seemingly overnight, Aniston was cast as a permanent victim in her own tabloid horror show and metamorphosed into Poor Jen, a role she has been stuck in for seven, long years.

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Now, after living in the eye of the sympathy storm for so long, Aniston’s new status as “happily engaged” leaves us to face a few uncomfortable questions about our obsession with Poor Jen. To wit: how did Aniston, despite her fortune ($110 million-plus), boyfriends (Vince Vaughn, Bradley Cooper and John Mayer to name a few) and enduring friendships (the ever-present Courteney Cox comes to mind), find herself condemned to being portrayed as the patron saint of the desperate and dateless? Or, as New York magazine put it, “America’s favourite spinster next door”?

Since the split, the tabloid media has remained doggedly fixated on the idea that Aniston must be desperate to rekindle her relationship with Pitt, spawning hundreds of articles with headlines like “Why can’t Jen let go?”; “Jen’s revenge romance”; and “Obsessed with Angie”.

In 2007, a cover of American OK! magazine proclaimed, “Jen’s lonely world” next to a photo of Aniston squinting into the sun during a Hawaiian holiday. Here was proof, supposedly, of Aniston’s miserable existence, TV’s former golden girl moping about on the beach, just herself, her washboard abs and a cadre of telephoto-wielding paparazzi for company. For years, every grainy paparazzi photo of her staring into the distance on a film set has been read as indelible proof she was still “heartbroken” or “devastated” about her divorce; every shot of her frowning slightly as she left a Starbucks offered up as unimpeachable evidence that she was inconsolable over the end of her marriage. Sans husband, the Poor Jen story went, she had been relegated to a life of power yoga, introspective beach breaks with Courteney Cox, and perpetual misery at her failure to keep Brad Pitt interested.

And, my, have we lapped it up. In the year to May, she appeared on no fewer than 78 magazine covers internationally, the vast majority agonising about her relationship with Theroux. And, when Aniston did get a boyfriend who seemed like he might be a keeper, like a clutch of fretting grandmothers, we obsessed about whether this new man would save her from a lifetime of spinsterhood and Sex And The City re-runs.

“America has been really worried about Jen. They want her to find happiness,” former marie claire US and Us Weekly editor-in-chief Bonnie Fuller told a morning TV show in New York in August. “Fans will be breathing a sigh of relief, probably opening champagne themselves. They have been waiting for their friend Jennifer Aniston to find Mr Right!”

Of course, part of the fascination comes from the fact that Poor Jen is just one point of the Aniston, Pitt and Angelina Jolie “love triangle” that has long since taken on mythical proportions. Like a bad soap opera, the same familiar plot lines and characters have been regurgitated/recycled over and over again: Angelina, smouldering and saving the world, one orphan at a time; Brad, torn between the Temptress and the Girl Next Door; and Poor Jen, the girl who Had It All, only to have it snatched away at age 36.

It’s a relatable fear. What happens if you get the fairytale husband and dream house – only to have your perfect life come crashing down?

Our enduring fixation with Aniston touches on a persistent, universal vein of anxiety about our vulnerability when it comes to our heart and future. Her story reminds us, no matter how famous or rich or yoga-toned we are, when it comes to love and children, so much of it lies beyond our reach. That is, we can’t control if we’ll meet someone with whom we want to have children. We can’t control whether or not our bodies will help us become mothers. And, we can’t control it if our partner will up and leave us out of the blue.

And therein lies part of our preoccupation with Aniston’s romantic fortunes. Right around the time she was meant to be getting serious about the whole motherhood thing, Aniston found herself home alone and nursing a broken heart, while her ex and his fecund new partner got busy creating the world’s most photogenic brood. With clockwork regularity, each time Pitt and Jolie welcomed a new addition to their family, Aniston’s childlessness was being held up in glaring contrast.

Professor Catharine Lumby, director of the Journalism and Media Research Centre at UNSW, agrees, and draws a parallel between the media’s fixation with Aniston’s non-mum status, and the treatment of Prime Minister Julia Gillard. “I think there’s still somehow this mythology that the only way for a woman to be fulfilled is to get the guy and settle down and have children. What we need to promote for women is choice and meaningful choice,” she says.

However, the persistence of the Poor Jen narrative not only robs Aniston of any agency over her own life, but reflects the ongoing challenges we face as women to define our own happiness. The preoccupation with Aniston has more to do with the fact that many people still struggle with the notion that a single woman, with no apparent desire to get hitched or knocked up, could be happy. The fetishisation of her single status over the years highlights the underlying societal convictions that still persist about the centrality of marriage and motherhood to a woman’s happiness. We might preach career, friendship and independence as modern tenets of contentment, but it can be argued that society still struggles with the idea that real joy and peace aren’t possible without a long-term relationship and babies. If we have to entertain the notion that Poor Jen might actually have been Totally Fine Jen for all those years, it means we would have to acknowledge that a woman could be fulfilled without having to be a mother or wife and that, like it or not, is still a confronting idea.

Sure, there might be a hint of the train-crash fascination in all this, too; of watching from afar as Aniston has had to contend with her ex’s blissful new life, splayed across the world’s media, in stark contrast to her solo existence. But deep down, there is a universality to the pain and humiliation of being dumped, and that makes the actress an intrinsically relatable figure. It also means Aniston’s story is one we read through the lens of our own experiences.

All of which is totally understandable, according to Professor Lumby. “I think we use celebrities like they are mythological gods, and the fascination with them is that people are able to project their own fears, hopes and desires onto these people.”

We don’t so much want a happy ending for Aniston as desperately need one. We need to be reassured that things will turn out all right for all of us, like a modern-day Cinderella story, but with a wedding ring and maternity bra at the end of it, because really, her fairytale is the fairytale we all secretly long for.