How to Date Again is a romantic comedy directed by Matt Flanders and co-written by the film's lead star, Rob Mor. It follows an emotionally blocked, heartbroken animator pushed back into the digital dating world by his chaotic best friend, culminating in a spontaneous California road trip. The film features a cast including Natasha Loring, Kevin Nealon, and Haley Joel Osment. 

@howtodateagain
IMDb

Animation Director / Randy Morales

Opening Titles — Stills
Pink background with white clouds and the text "TALLBOY PRESENTS" in yellow
A scenic landscape with a purple lake, a sandy shore with flowers, a large mountain, and a partly cloudy sky. Text over the image reads: In association with In your face entertainment.
An illustration of a lake with a mountain in the background, pink sky, flowering plants at the shore, and two people on a swan-shaped boat. Text reads 'To Date Again'.
Illustration of a vinyl record player with the text 'Natasha Loring' over the record.
A colorful animated scene with the name 'Johnny Wilson' displayed. There are two martini glasses with olives on a table, a pink flower, and a bowl of spaghetti with chopsticks. In the background, a black cat is lying on a teal sofa, and a small white dog stands on the floor facing the sofa. Pink curtains are partially visible behind the sofa.
Animated scene showing a purple sky with a crescent moon and a woman sitting on it, with curtains partially open revealing this scene and text indicating the presence of Haley Joel Osment.
An animated billboard with a cartoon boy holding a hamburger, and text that reads 'and Emilio Rivera' against a purple sky background.
Close-up of a window and door with pink tulips in pots outside on a brick wall
Animated scene showing a sunset over mountains with a pink sky, part of a brick building on the left, a teal car in the foreground, and a sign indicating vacancies and menu items like coffee, pastries, and steak.
Living room scene with two people sitting on chairs, coffee table, and plants, with yellow text overlay reading 'Directed by Matt Flanders'.
Title screen of an animated film showing the screenplay credits for Rob Mor and Matt Flanders, with a living room interior and a cartoon character sitting on the couch.
A collage of storyboards for an animated production, featuring sketches and colored illustrations of landscapes, characters, and settings, including lakes, mountains, and indoor scenes. Several segments display names of contributors and production roles, such as Rob Mor, Natalia Laoring, Emilio Rivera, and others. 
Opening Titles — Storyboard & Style Frames
Overlays
Dream Sequences — Pirate Ship & Heart Planet
A woman with pink hair in a purple dress stands on the deck of a boat, gazing at a sunset over the water.
Animated scene of a woman on a boat waving with a sunset sky in the background, featuring mountains, clouds, and a shark silhouette in the sky.
Animated illustration of two astronauts floating in space next to a large red heart-shaped asteroid with stars and planets in the background.
Two cartoon astronauts are floating in space, each inside half of a broken heart-shaped asteroid, with a space background of stars and planets.
An illustrated person with red hair wearing a space helmet and a white space suit, floating in space with planets and stars in the background. 
Dream Sequences — God
Digital illustration of an art gallery with paintings on purple walls and a person at a computer desk at the back of the room, viewed from above among clouds.
A woman with purple hair sitting at a desk with a computer, with a radiant light and mountains in the background.
Digital illustration of a person with blonde hair, wearing a pink jacket, walking in a colorful mountainous landscape with pink tulip flowers along a winding path, purple trees, and mountains under a pink sky with clouds.
An animated angel with pink wings flying over mountains and clouds in a pink sky.
A girl sleeping on a crescent moon with a purple background, stars, clouds, and a flying angel girl dressed in purple with wings.
Illustration of a nighttime rural landscape with colorful houses on rolling hills, trees, and a starry sky with a crescent moon. A girl is sleeping on the moon, floating above the scene. 
Dream Sequences — Beach Walk
A calm night scene with a full moon over purple sky, reflecting on the water near a sandy beach, with a sailing ship in the distance.
A couple walking on the beach under a full moon at night with a ship in the water and mountains in the background.
A cartoon couple standing barefoot on a beach at night under a full moon with purple sky, stars, hills, and trees in the background.