06/18/2013 08:27 pm ET Updated Feb 02, 2016

The Many Mothers of Cinderella Boy: A Review of A Kid Like Jake

What if Cinderella attended the wrong ball? What if she'd been asked to catch a ball (instead of dance) and was ridiculed when she refused? What if Cinderella were a 4-year-old boy named Jake whose parents desperately want him to get into an elite private school?

These are among the questions raised by the new play A Kid Like Jake, which opened Monday, June 17, at Lincoln Center. Like most non-musicals in New York City these days, the context here is contemporary, upper-middle-class "white people" problems. However, unlike several of its peer productions, which feature myopic, sterile conflicts of the "to sip cocktails or not to sip cocktails?" variety, the stakes here are high and broadly relevant: namely, how does one effectively parent a gender-nonconforming boy in the face of norms wickeder than a fairy-tale stepmother?

The play opens much like the Cinderella story, with a mother plotting anxiously to secure her child's "royal" status, and therefore her own; in this case, status means enrollment in a fancy private school. Though we never meet the child in question, Jake, we learn right away that princesses inspire his play, and that his parents seem more than cool with that (e.g., buying him every princess doll, book, and movie on the planet), hence the central question of the play: Can Jake's parents be progressively attuned to his unique sense of self and be status-quo/status-hungry at the same time? In other words, can this be achieved without Cinderella's mother becoming her evil stepmother?

When Jake's mother, Alex (played with fierce, empathic conviction by Carla Gugino), meets with the principal of his preschool, Judy (a sharp and dropped-in Caroline Aaron), for advice on gaining admission to a top-tier grade school ("the ball"), the plot becomes more complicated. Is Judy a fairy godmother, and if so, whose: Jake's or Alex's? Judy is highly attuned to Jake, including his "gender-variant play," which she explicitly names and encourages Alex to make use of in school application essays. But Alex shudders at the words, apparently having dissociated from the princess-play she has been encouraging and participating in at home. Instead, Alex pleads with Judy to use her "magic" connections (and discreteness) to squeeze Jake into the best possible school by underplaying his gender variance.

As the school interviews commence and Jake is encouraged to contort his behaviors, he becomes aggressive, acting out some of the more violent moments from the Grimms' Cinderella story: drawing bloody pictures of the stepmother as she cuts her daughters' feet to fit the glass slipper. Of course, this instigates a cycle of rage as Jake fails to get into many of the schools, exacerbating Alex's disappointment and frustration and leading her to become more and more controlling ("wicked") as the play progresses.

And then something unexpected happens: The playwright gives us access to Alex's inner life by way of a dream sequence. We begin to understand her as someone who has confronted the pressures to give up her own "girly play" in order to gain status. We learn that she worked as a lawyer before choosing to raise Jake full-time, and that the fear of failure has always pervaded her life. We begin to appreciate the many hours she spent alone raising Jake, in a fantastic play space she created for them, where each of their "girly" desires could safely, mutually expand and not be shunned -- where each of them could be Cinderella. We also recognize the great loss they both share when the clock strikes midnight, the carriage becomes a pumpkin, and social norms reclaim them.

A similar mother/son dilemma appears in psychoanalyst Ken Corbett's book Boyhoods: Reclaiming Masculinities. Corbett describes his work with a gender-nonconforming boy and his mother, who accepted his "girly play" but struggled with his need to be "pushy" about it, often saying, "Everything is princess this, and princess that." Corbett eventually helped the mother address her ambivalence about "girly play," locate her own childhood "pleasures of exhibitionism" and "being the object of desire," and identify the shame she learned to link with those pleasures (i.e., the pressure she felt to conceal those desires and contort herself so as to gain respect and status in a man's world). As an alternative to modeling this anxiety and shame for her son, Corbett helped the mother create a reflective space (rather than a punitive one) in which they could talk about the dilemmas they faced together. Fortunately, by the end of A Kid Like Jake, Jake and Alex seem to be on a similar trajectory toward reflection and understanding.

As much as we may cringe at yet another play about wealthy New Yorkers, not only does A Kid Like Jake present a more thrilling premise than most, but the core conflict is also arguably enhanced by the privileged setting. The dilemma of wanting to be a boastful, proud, attuned parent of a fully self-expressed child while also wanting to be the boastful, proud, disciplined parent of a private-school enrollee is a high-stakes conflict of interests faced by those who can afford it. Though various dilemmas regarding the parenting of gender-variant children in public vs. private settings take place in all our communities, watching class-conscious parents negotiate the advantages of conformity vs. nonconformity is particularly theatrical. It also challenges us to consider our own parenting values when faced with questions of our children's mental, emotional, and physical well-being.

The more stories of gender-variant children that we share on our stages and screens, and the more conversations we have about the various challenges gender variance presents, the more safe, reflective spaces we can offer "princess boys" and their families, in all our communities, not only in New York City's wealthiest.

In the meantime, give yourself 115 minutes of reflective space on these issues by seeing A Kid Like Jake.

A version of this piece was first published in dot 429 Magazine.