Private Project

How to Date Again

A heartbroken animator, reluctant to get back out there, gives love another shot with the help of friends, fate, and a fantastical first date.

HOW TO DATE AGAIN is a high-concept, character-driven romantic comedy with a modern twist. It merges emotional depth with offbeat humor, stylized animation, and the anxiety-inducing chaos of app-based dating. At its heart, the film is about love, grief, friendship, and the strange new rules of connection in the digital age.

The story follows Michael (Rob Mor), a once-successful animator reeling from a heartbreak so brutal it’s seeped into his dreams… and his drawings. Pushed back into the dating world by his chaotic but well-meaning best friend Xander (Johnno Wilson), whose therapy involves mushrooms and unsolicited pep talks, Michael embarks on a reluctant romantic comeback. After a series of dating disasters, he meets Leigh (Natasha Loring), a ranch-dressing-obsessed, emotionally intuitive record exec who might just be weird enough to match his brand of broken.

Michael and Leigh meet at a hipster bar in East L.A., visit the swoon-worthy, swan-shaped paddle boats in Echo Park, and bond over records at his Silver Lake bungalow. They come to realize that they’re both stuck in the past and need an adventure to help them move on. A spontaneous road trip with a stopover at an iconic drive-in (Bob’s Big Boy) and overnight stay at a hilariously offbeat hotel (The Madonna Inn) become the backdrop for one of the most authentic and singular first dates ever put to screen. They visit a new-age bookstore, the stunning coastline of Morro Bay, and a horse ranch in the gorgeous hills of California. They also sample the most epic breakfast sandwich of all times. HOW TO DATE AGAIN isn’t just a love story; it’s a love letter to The Golden State.

Along the way, Michael is tracked by Xander and his girlfriend Kai (Amanda Payton), who are concerned about their down-and-out friend’s sudden disappearance. We also meet a delightfully creepy hotel night manager (Haley Joel Osment), a gruffly loveable rancher with his own story of loss (Emilio Rivera), and Michael’s therapist (Kevin Nealon), who is convinced he’s dating a porn star even though he’s never met her. Through it all, we’re treated to animated dream sequences, viral-dating-profile-style graphics, a killer soundtrack (Belle and Sebastian, Big Thief, Searows), and a deeply relatable portrait of modern loneliness and hope.

As must happen with all good things, the date comes to an end, and Michael and Leigh say their goodbyes. But they leave knowing they’ve been changed for good and are ready to move forward, with or without each other. Is Leigh just the person Michael needed to teach him how to date again? Or is she his FANTASY woman, in every sense of the word?

With a sharp, authentic, and contemporary voice in the tradition of films like 500 DAYS OF SUMMER, MY OLD ASS, and PALM SPRINGS, HOW TO DATE AGAIN is positioned to resonate with millennial and Gen Z audiences hungry for smart, emotionally-honest rom-coms. The script blends comedy and catharsis with stylistic flair, based-on-a true story appeal, and a twist ending, setting the stage for a film that is both commercially viable and creatively fresh.

This is a contained, low-budget project with strong potential for festival play, streaming platform acquisition, and cross-platform marketing, especially through its visually distinct style and social-media-savvy themes. HOW TO DATE AGAIN isn’t just another romantic comedy. It’s a post-heartbreak survival story about two people trying to heal and learning that connection, even when messy, is worth the risk.

BACKSTORY:
HOW TO DATE AGAIN is more than a film. It’s a testament to how art, creativity, and humor can help us move through grief. Our producer, co-writer, and star who portrays Michael, Rob Mor, was with the love of his life, Noel, for ten years. Four months after their daughter Leia was born, Noel was diagnosed with ovarian cancer. She passed away when she was just 31.

In 2022, Rob made a short film about their story called GHOSTED. It was a fantastical imagining of what it would be like if Rob had the chance to go on a date with Noel one last time. The film won numerous awards and moved people struggling with their own grief and loss. Now it’s time to bring this heartwarming story and its message of hope to a larger audience with the feature film HOW TO DATE AGAIN.

  • Matt Flanders
    Director
  • Rob Mor
    Writer
    Ghosted
  • Matt Flanders
    Writer
  • Rob Mor
    Producer
    Ghosted
  • Josette Eales
    Producer
  • Matt Flanders
    Producer
  • Rob Mor
    Key Cast
    "Michael"
    Ghosted
  • Natasha Loring
    Key Cast
    "Leigh"
    Ghosted
  • Johnno Wilson
    Key Cast
    "Xander"
    Ghosted, I Love That For You, Twisted Metal
  • Haley Joel Osment
    Key Cast
    "Hugh"
    6th Sense, Happy Gilmore 2
  • Kevin Nealon
    Key Cast
    "Larry"
    Weeds, Happy Gilmore 2
  • Amanda Payton
    Key Cast
    "Kai"
    Hacks
  • Emilio Rivera
    Key Cast
    "Rancher"
    Sons of Anarchy
  • Luke Hanlein
    Director of Photography
  • Project Type:
    Feature
  • Genres:
    Romantic Comedy, Dramedy
  • Runtime:
    1 hour 36 minutes
  • Completion Date:
    September 22, 2025
  • Production Budget:
    500,000 USD
  • Country of Origin:
    United States
  • Country of Filming:
    United States
  • Language:
    English
  • Shooting Format:
    Digital Alexa 35
  • Aspect Ratio:
    16:9
  • Film Color:
    Color
  • First-time Filmmaker:
    No
  • Student Project:
    No
  • Digital Cinema Package:
    Unavailable
Distribution Information
  • Archstone Entertainment
    Sales Agent
    Country: Worldwide
    Rights: All Rights
Director Biography - Matt Flanders

Matt Flanders is an independent writer, director, and producer. He is currently producing THE FARNSWORTH HOUSE, written and directed by Richard Press and starring Elizabeth Debicki and Ralph Fiennes. He is also the writer and director of the upcoming black comedy IT WAS A BLAST, starring Zosia Mamet, Andrew Rannells, Conrad Ricamora, Evan Jonigkeit, and Zoe Chao. Other producing credits include Tony Stone’s TED K starring Sharlto Copley (Panorama, Berlinale), Danny Sangra’s GOLDBRICKS IN BLOOM, and Alexandra Boyd’s WIDOW’S WALK.

Before starting his own production company, In Your Face Entertainment, Matt worked in production and development at Brad Pitt’s Plan B Entertainment. During his five years there, he assisted with projects like Ryan Murphy's EAT, PRAY, LOVE, Andrew Dominik's KILLING THEM SOFTLY, Marc Forster's WORLD WAR Z, and Steve McQueen's TWELVE YEARS A SLAVE.

Matt wrote the episode D AS IN DELTA for the anthology series FABLED and has written and produced dozens of live televised events including the MTV Video Music Awards, Trailblazer Honors, The White House Mental Health Youth Action Forum, New Year’s Rockin’ Eve, and red carpet shows for the Grammys, Golden Globes, and Oscars.

Matt graduated from Gonzaga University with a degree in theater and has directed improv, musicals, and plays throughout the United States. He also studied French civilization at the Sorbonne in Paris and cinematography at NYU. He taught acting in the New York City public school system and at numerous summer theater programs and ran filmmaking workshops for young adults with autism through Joey Travolta’s Inclusion Films. Originally from Helena, Montana, he now splits his time between New York City and Upstate New York.

Add Director Biography
Director Statement

In 2019, Rob Mor, the producer, co-writer, and star of our film, HOW TO DATE AGAIN, lost his young wife, Noel, to ovarian cancer just two years after giving birth to their first child. To channel his grief, Rob made a comedic short about what it would be like to go on one last date with Noel. Seeing how the film helped others dealing with loss, he decided to make a feature film to bring his story to a broader audience.

I was originally approached to help develop the feature script in April of 2025. Having recently lost a dear niece who I helped raise, I connected with the material immediately and offered to do a rewrite. Rob and producer Josette Eales were moved by my take and asked me to direct. I knew I was the right leader for this project because, like Rob, I’m a person who navigates grief with creativity, humor, and hope. And as a first-time feature director who has spent nearly two decades helping others make their movies, I love a good story about starting over. Our small but outstanding crew fell into place quickly, and the original cast of the short was joined by Kevin Nealon, Haley Joel Osment, Emilio Rivera, and Amanda Payton. We started principal photography just six weeks after I came on board. It all felt meant to be.

At its core, HOW TO DATE AGAIN is a romantic comedy, but one that carries the weight of grief and the tenderness of moving on with grace. Humor and heartbreak can go hand in hand, and laughter is often the first sign that life is returning after loss. The film balances clumsy attempts at dating with quiet beats of memory, grief, vulnerability, and courage. It explores the paradox between honoring the past and daring to love again.

Stylistically, the film is grounded, intimate, and emotionally accessible. Our lead character is a Silver Lake creative and music lover, so we’ve infused animation, graphics, and a killer soundtrack to heighten the joy and hope, but also the loneliness and longing. The film also features gorgeous California landscapes, the vibrancy of Los Angeles, and the quirkiness of The Madonna Inn in San Luis Obispo. The comedy always comes from the heart and the characters, not gimmicks. The protagonist’s friends push him forward by staying true to who they’ve always been and helping him laugh through his pain.

I hope HOW TO DATE AGAIN, with its universally relatable themes, healing message, twist ending, and based-on-a-true story appeal, finds a wide audience through exposure at festivals, and then, through greater distribution. People need a movie like this right now. I want audiences to laugh, to feel the sting, and to leave knowing things do get better. Grief never fully disappears, but it can coexist with joy.

Matt Flanders
Director / Co-Writer / Producer
HOW TO DATE AGAIN