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How a Trip Around the World Turned This Guy Into a Romance Author

James Bailey has accomplished a lot, but now he's attempting the impossible: getting dudes to read love stories

In the vast wilderness of the literary world, a rare form of author exists: the male romance writer. They’re so rare, in fact, that many believe them to be nothing more than mythical creatures. But with the release of his debut romantic comedy, The Flip Side, 29-year-old James Bailey reminds us that male romance authors like himself are indeed real after all. “Romance and love are universal, they aren’t just female experiences,” explains Bailey who, by day, is an alumni relations and events coordinator for a boys school in the U.K. 

Ironically, Bailey’s interest in matters of the heart started because of a serious ailment with his own. At 17, he was diagnosed with a rare heart affliction called Wolff-Parkinson-White syndrome. After undergoing two operations, he was ultimately cured, but he says the experience left him with a “seize the day” mentality. As such, he’s since run the London Marathon, carried the Olympic Torch, made a speech at the House of Commons and appeared in a segment of BBC1’s Lifeline, all on behalf of Cardiac Risk in the Young, a charity that had originally diagnosed him with his condition.

Still, after college, he found himself a bit aimless. “I didn’t know what to do with my life,” he says. And so, in Eat, Pray, Love style, he decided to travel around the world in an attempt to find himself — and romance. But despite criss-crossing 21 countries in less than a year, Bailey jokes that enlightenment and love ultimately eluded him. It was, though, the sum total of these experiences that inspired the premise of The Flip Side.

The novel opens with its main character, Josh, manically devouring truffles and champagne while trapped in a private pod of the London Eye with his now ex-girlfriend. She has not only just declined his marriage proposal but also confessed her ongoing affair with an older man and her desire to break up. Devastated, and feeling like he’s only made the wrong choices in life, Josh decides that, for one year, he will allow a coin flip to determine all of the major decisions he’s presented with, which ultimately sends him across Europe and into the arms of new love.

In addition to Bailey’s own travels, the teenage students at his school served as significant inspiration for The Flip Side. “You grow up with this image that you have to be a certain way as a man,” he tells me, explaining that boys have absorbed the belief that they must have a “strong upper lip and just get on with stuff.” Bailey, then, wanted to give them an example of a young man in his 20s who experiences multiple common heartbreaks — e.g., losing a girlfriend, a job, an apartment and beloved grandparent — but who is able to express his feelings of sadness and move on in a healthy way. “I want them to know it’s okay to talk about their feelings, and if they’re upset, that it’s better to talk about it,” he says.

At the same time, he wants his adult readers to see more realistic portrayals of men, too. “Ninety-nine percent of us are going to experience heartbreak at some point in our lives, so it’s important that men feel it’s okay to be sad [when it happens],” he argues, especially because, in his estimation, when in comes to love and romance in pop culture, women are allowed to completely succumb to the devastation of a heartbreak, while men are either the instigators of emotional pain or miraculously move on from it in under two minutes. After all, he says, “There are men out there who are equally as heartbroken as women when they break-up.”

But if Bailey wanted to get his message to more men, why did he choose a genre dominated by female readers? 

His main priority was to tell his story in a lighthearted way that would make readers laugh. And since he routinely watched romantic comedies as a kid with his mother, the rom-com structure came most naturally to him. Besides, he says, the term “chick-lit” “is demeaning to the genre,” arguing that such works should instead be held in the same kind of esteem as movies like Annie Hall, which is how he views the best of the genre (and what he was aiming for).

Better yet, to Bailey, romance novels allow us to escape into a world where a happy ending is almost always guaranteed. Which is both a balm for a world currently trapped in the throes of a deadly pandemic — to that end, he hopes The Flip Side will serve as a reprieve by providing the “opportunity to laugh and remember the good times where you could meet up with friends” — and in Bailey’s estimation, totally independent of gender.