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In Maya Jax's Escapades of Romantically Challenged Me, Lelaina, an aspiring screenwriter and dating disaster, is busy impersonating a superhero to gain the attention of a Hollywood agent when she finds out that her dad has had a heart attack. Leaving LA for the first time in three years, she returns home to be with her family. And now that she's back, her parents want her to stay and join the family law firm. After three years of unsuccessfully trying to "make it" in Hollywood, she thinks they might be right. But soon after settling into her new life, Hollywood calls with a potential offer. Lelaina has to decide if she'll stay for her ailing father and the promise of a successful life, or return to LA to pursue what she's always wanted. Torn between her two choices, the decision becomes even harder when her cheating ex reappears with apologies and a proposition.