All You Need to Know About the 'Playing Pretend' Cast and Story

What starts as a fake engagement between a demanding CEO and his longtime assistant soon turns into something far more complicated in Candy Jar's "Playing Pretend." Here's everything to know about the series' heartfelt story and the cast led by Anna Marie Parsons and Cayman Cardiff.

Fake dating is one of romance's most enduring tropes, and "Playing Pretend" builds its story around a familiar setup that quickly becomes more complicated.

Starring Anna Marie Parsons and Cayman Cardiff, the Candy Jar series follows two people whose staged engagement begins as a business arrangement but gradually develops into something much more personal.

Cayman Cardiff as Brennan Wolf and Anna Marie Parsons as Grace Reynolds in "Playing Pretend" | Source: instagram/crazystonestudio

What Is "Playing Pretend" About?

"Playing Pretend" centers on Grace Reynolds, who has spent three years working as the personal assistant to Brennan Wolf, a wealthy businessman known for his demanding personality and endless string of romantic flings.

While Grace has long managed both his professional and personal chaos, the loss of her mother forces her to reevaluate her own life and finally decide to resign.

Anna Marie Parsons as Grace Reynolds in "Playing Pretend" | Source:instagram/crazystonestudio

Brennan agrees to release her from her contract—but only if she does him one last favor. He needs Grace to pretend to be his fiancée during his sister's wedding weekend, creating the perfect appearance for his family.

What begins as a temporary arrangement soon becomes far more complicated as old emotional wounds, growing attraction, and unexpected vulnerability blur the line between performance and reality.

Anna Marie Parsons and Cayman Cardiff in "Playing Pretend" | Source: instagram/crazystonestudio

Based on R. S. Burton's novel of the same name, the story combines several popular romance tropes, including fake dating, boss-and-assistant romance, forced proximity, and emotional healing.

As Grace and Brennan spend more time together, the relationship they originally staged for others slowly becomes genuine, forcing both characters to confront their pasts and reconsider what they truly want from life and love.

Anna Marie Parsons as Grace Reynolds

Anna Marie Parsons leads the “Playing Pretend” cast as Grace Reynolds, Brennan Wolf's capable assistant whose decision to resign sets the story in motion.

Although Grace initially agrees to Brennan's unusual request simply to fulfill one final obligation, the weekend forces her to confront feelings she has long kept buried while discovering new confidence in herself.

Anna Marie Parsons as Grace Reynolds in "Playing Pretend" | Source: instagram/crazystonestudio

Parsons has built experience across independent films, television projects, and theater productions. Her credits include "No Exit," "12 Till Dawn," and "Friday the 13th: The Awakening" before taking on the lead role in "Playing Pretend."

She studied scene work, improvisation, script analysis, and the Meisner technique, and also holds a bachelor's degree in business administration from the University of Tennessee.

Her résumé describes her as an actress known for combining humor with authenticity, qualities that align well with Grace's journey from dependable assistant to romantic lead. Beyond acting, Parsons has experience in athletics, dance, singing, and horseback riding, reflecting a versatile performance background.

Anna Marie Parsons as Grace Reynolds in "Playing Pretend" | Source: instagram/crazystonestudio

Cayman Cardiff as Brennan Wolf

Cayman Cardiff plays Brennan Wolf, Grace's demanding boss whose proposal for a fake engagement drives the story's central conflict.

Initially introduced as a successful businessman accustomed to controlling every situation, Brennan gradually reveals a more vulnerable side as his relationship with Grace evolves beyond the arrangement they created for appearances.

Cayman Cardiff as Brennan Wolf in "Playing Pretend" | Source: instagram/crazystonestudio

Born in Lexington, Kentucky, Cardiff earned a Bachelor of Arts degree in Spanish from the University of Utah before relocating to Los Angeles to pursue acting professionally. His IMDb biography notes that he has since appeared in more than 25 vertical dramas while also expanding into writing, directing, and producing.

Cayman Cardiff as Brennan Wolf in "Playing Pretend" | Source: instagram/crazystonestudio

He also shared that his biggest goal as a performer is to tell stories that inspire empathy and meaningful human connection, explaining that he wants to create work that motivates people and encourages them to better understand one another.

Who Else Appears in "Playing Pretend"?

While the romance centers on Grace and Brennan, several supporting characters help shape the couple's journey. Caroline Carter appears as Jacqueline Wolf, while Victoria Herda plays Kate Wolf and Jpatrick McCann portrays Samuel Wolf, members of Brennan's family whose wedding weekend becomes the backdrop for the fake engagement.

The supporting cast also includes Victoria Doctor as Belle, Peyton Suzuki as Naomi, and Nicholas Eric Wills as Alec, rounding out the characters who populate Grace and Brennan's world throughout the series.