Dating Over You 2026
"Because the next one might be the one"
In *Dating Over You (2026)*, director Josh Keeler crafts a sharp, brisk romantic comedy that follows Jake's post-breakup journey—less about healing and more about the chaotic energy of avoiding his own emotions.
Director: Josh Keeler
Cast
Frequently Asked Questions
What is Dating Over You (2026) about?
*Dating Over You* follows Jake, a recently heartbroken guy who tries to rebound from a breakup by diving into new relationships. When distraction becomes his only coping mechanism, he learns that running from his emotions might be a faster route to the wrong kind of love. The film blends humor with a surprisingly tender exploration of modern dating.
Who directed Dating Over You?
The film is directed by Josh Keeler, a filmmaker known for his keen eye for sharp dialogue and relatable comedic timing.
Who stars in Dating Over You?
The lead role of Jake is played by Reggie Herold, with Natalie Shershow, Lila Chapman, Hannah Lauren Wilson, and Aubrey Gainous rounding out the core cast.
Is Dating Over You (2026) worth watching?
With its 8-minute runtime and sharp comedic edge, *Dating Over You* is a quick but satisfying watch for fans of romantic comedies. While it's too early for user ratings, its premise and cast suggest a lighthearted, entertaining experience that's perfect for a short film night.
How long is Dating Over You?
The film runs for 8 minutes.
🎥 Trailer
About Dating Over You (2026) — A Post-Breakup Rom-Com That's Equal Parts Funny and Relatable
In *Dating Over You (2026)*, director Josh Keeler crafts a sharp, brisk romantic comedy that follows Jake's post-breakup journey—less about healing and more about the chaotic energy of avoiding his own emotions. When a recent split leaves him adrift, he dives headfirst into the dating pool, convinced that distraction is the key to moving on. With its biting humor and heartfelt moments, the film explores the absurdity of modern romance and the messy, sometimes hilarious ways we attempt to outrun our own feelings. Set against the backdrop of everyday chaos, *Dating Over You* balances wit with warmth, making it a standout in the genre.
Starring Reggie Herold as the lovably flawed Jake, Natalie Shershow as his sharp-tongued best friend, and Lila Chapman in a scene-stealing supporting role, the ensemble brings authenticity to this micro-comedy. The film's tone—playful yet poignant—reflects the push-and-pull of dating in the digital age, where every swipe feels like a chance at redemption, even when it's not.