In his directorial debut, Fantasy Life, Matthew Shear said he worked with a dream cast of highly experienced and well-known actors, including Amanda Peet and Judd Hirsch.

Mr. Shear is a regular visitor to the Island, having first come in 2015 when his best friend invited him to stay for the summer. While on Island, he worked at the Chilmark Community Center as a camp counselor and was in a Midsummer Night’s Dream at the Tisbury Amphitheater.

Now a professional actor and director, Mr. Shear shared the journey of filming Fantasy Life with an audience at the Grange Hall on Saturday night as part of Circuit Stage’s summer programming.

Matthew Shear and Amanda Peet. — Jeanna Shepard

“What I experienced with every one of these incredible character actors was that they were normal, nice, collaborative and interested in the script,” Mr. Shear said. “It was a delight. That’s really all I can say.”

One of those actors shared the stage with Mr. Shear at the Grange Hall: seasonal Vineyarder Amanda Peet.

Ms. Peet said she was drawn in by Mr. Shear’s smart, sane and collaborative nature. Above all, she was appreciative of his feelings toward mental illness that were prevalent in the script.

“As soon as I read it, I was like, oh, this person has an incredible sensitivity about mental illness and when we see movies about mental illness we think of like...these really dramatic people who were on the outskirts of society and I really loved that in this these people are really high functioning but also really struggling,” she said.

Event was part of Circuit Arts' summer programming. — Jeanna Shepard

Fantasy Life tells the story of Sam Stein, a paralegal who has recently lost his job and ends up babysitting his psychiatrist’s three granddaughters. The film reveals his difficulty with his new position and his blooming admiration for the mother, Dianne (played by Ms. Peet), as the two of them form an unlikely companionship and relate over their struggles with mental health.

Martha’s Vineyard also plays a role in the film as the characters’ summer destination. Despite only one scene being filmed on the Island due to budget and logistical constraints, Mr. Shear said he was determined to have the story set here.

“I wrote the script and it took place on Martha’s Vineyard. I was very rigid about that,” he said. “I was pitched other ideas for other places like the Hamptons and stuff more practical for shooting, and I just felt that it had to be on Martha’s Vineyard.”

In writing the script, Mr. Shear said he often drew from real-life experiences and personal connections.

“I went in with some personal aspects of my life and I just kind of found a tapestry of characters that were all reminiscent of family members and psychiatrists and all kinds of people,” he said.

Mr. Shear said he initially approached the script thinking he would eventually find a director to make the film but struggled to get anyone interested. Then he decided to direct it himself.

“I started to sort of read a lot about directing and YouTube and just became obsessed with it and developed a lot of intense confidence about it,” he said.

He said the real turning point in the process was when he offered a part to Ms. Peet and she was interested.

Ms. Peet said the genuineness of the characters and story appealed to her from the start.

“I think when I read the script, I thought it was really beautiful, and I thought that it was really funny and that Matt had a great voice, and I felt like I could really relate to it,” she said.

The film officially comes out in theatres in March, Mr. Shear said, adding how grateful he is for all who helped out.

“It was a major joint effort,” he said. “Just so many things that came together happened amongst a group of people extremely dedicated to it happening... It’s a miracle that happened,” he said.