Any resemblance between the title character of Gina Gionfriddo’s play and Becky Sharp, the heroine of William Makepeace Thackeray’s novel “Vanity Fair” is purely and presumably intentional. But whether or not there is a glimmer of similarity between the two women is somewhat incidental. But this doesn’t make Gionfriddo’s play any less contentious in regards to her presumed heroine who, like her 19th century counterpart, is as determined to satisfy her emotional needs as she is motivated to tactically and aggressively use all her wiles and resources to upgrade her social standing.

A resounding success at this year’s Humana Festival of New American Plays, “Becky Shaw” is an amusing and craftily constructed comedy about ambition, the cost of being truthful, and the perils of a blind date. While director Peter Dubois has kept just two of the original five actors, the current ensemble appears impeccably prepared for their roles. Yet what are we to make of a play in which there is not a single character for whom we can root or a contrived plot that is hardly worth a second thought? I’m not sure I know the answer. After two hours in the company of Gionfriddo’s five distinctively perverse and disingenuously dysfunctional characters, I was not sure what lesson I was to learn, what insight I might gain, or what resolution I was to ponder. All that and I have to admit to having a good time, laughing a lot, and when it was over still thinking about what I surely had missed.

Gionfriddo, who made a splash at the Humana Festival with her first play, “After Ashley,” in 2004 and subsequently with a production at the Vineyard Theater, also writes for the TV series “Law and Order.” She will undoubtedly get even more attention with this play in which a seemingly unassuming, impoverished, unmarried but attractive 35-year-old woman succeeds in unsettling the quirky status quo of a family of means.

While Becky, as played with a disarming, carefully calibrated sincerity by Annie Parisse, is the catalyst for change and the one character most easily defined by her schematic behavior, it is left for the other four characters to deftly defy our expectations and subvert our understanding of human nature. One of the most fascinating aspects of the play is the way each character, in turn, becomes the engine for the next surprise.

While in a protracted state of mourning for her father, the 35-year-old Suzanna (Emily Bergl) is also feuding with her mother, Susan (Kelly Bishop), over the family’s finances and the hastiness with which Susan, despite coping with multiple sclerosis, has found love with a young con artist who by the second act is headed for prison. For most of her life, Suzanna, who is working towards a degree as a therapist, has put her trust in Max (David Wilson Barnes), the family’s financial planner, who is committed to being more than a mediator between the two women. After his mother died, Max was abandoned by his father and raised by this family since he was 10 years-old. Now a successful, glib, and cynical business executive, Max considers the present to be a turning point with regard to his life-long attraction to the high-strung, emotionally needy Suzanna.

Taking Max’s advice to help heal the loss of her father, Suzanna goes on a ski holiday and meets Andrew (Thomas Sadoski). Eight months later, Suzanna remains emotionally bonded to Max but is now married to Andrew, a nice looking, uncomplicated, law office manager of no particular distinction except that he wants to help every needy person he meets. A good deed doer, Andrew arranges a blind date for Max with Becky, a pretty 30-something-ish co-worker. It is in the scene in which Becky arrives at Andrew and Suzanna’s apartment dressed, as Max says, like a “birthday cake,” that the play begins to put these seriously flawed individuals into concerted perspective.

It would seem that Becky is in over her head, but she holds her own among the inquisitors spouting Gionfriddo’s funniest rejoinders. Gionfriddo has us laughing equally hard at Max’s brutal badgering, Susan’s eccentricities, Andrew’s naivete, and Suzanna’s kvetching. The blind date doesn’t go well for reasons that I won’t give away, but through the dynamics of David Wilson Barnes’ brilliantly abrasive performance, Max might easily be labeled a charmless cad. His reprehensible behavior in regards to romantic love is only subordinate to his callous insensitivity toward everyone’s feelings.

Suzanna’s inexplicable dependence on Max is another issue that is factored into the mix, particularly in the light of Andrew’s somewhat over-the-top concern for Becky. Suzanna is the play’s most perplexing character but Bergl finds her most genuine side as Suzanna begins to grasp the fact that her marriage is at risk. And considering all that is at risk, there is something to be said for acknowledging Suzanna as the real heroine and Becky merely the titular intruder. Gionfriddo doesn’t make this clear. Sadoski is appealing as the good-natured Andrew, who unwittingly initiates opportunity for another romantic disaster.

The scene-dominating Bishop doesn’t get enough stage time. She is terrific as the idiosyncratic, autocratic Susan, who knows how to maintain control of her life and those around her: “I’m going to buy you both a wonderful dinner and some really excellent wine. We’ll have a nice evening and put all of this behind us. But first we have to go to prison.” Derek McLane’s scenic designs provide a smooth transition from one location to the next, prison excluded. ***

“Becky Shaw,” through March 15, Second Stage Theater, 307 West 43rd Street. $70. 212-246-4422. Patrons age 30 and under may purchase a limited number of specially-priced $30 tickets in advance. A limited number of student rush tickets are $15 and are available 30 minutes prior to curtain.

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