Akwire Media Group · Original Motion Picture
Jack in the Box
A Romantic Comedy · Coming Soon
“The best love stories are the ones already written.”
- Genre
- Romantic Comedy
- Format
- Feature Film
- Status
- In Production
Logline
After years of choosing work over love, guarded cyber analyst Allegra reconnects with her charming college best friend Jack, forcing them both to confront old heartbreak, missed timing, and the possibility that the love they were searching for was always right in front of them.
Synopsis
A swipe.
A spark.
A second chance.
Allegra is a successful cyber analyst who has built an impressive career — and an even more impressive wall around her heart. After a painful breakup, she buried herself in work, insisting to her best friend and roommate Sierra that she is perfectly fine staying focused on the job. But Sierra sees through the act, pushing Allegra to open up to love again.
Across town, Jack is a funny, messy, warm-hearted software engineer nursing his own heartbreak. He is funny, disarming, and just as stuck in his comfort zone as Allegra is in hers. When the two match on a dating app, the conversation starts with witty banter — and ends with a shock: they were once best friends, inseparable through high school and college, before life pulled them apart.
Their reunion reignites old memories, effortless laughter, and a chemistry that feels anything but new. What begins as a casual dinner turns into a beach day, then a romance that makes both of them question the walls they built. But Allegra’s fear of vulnerability and her demanding career cause her to pull away, leaving Jack confused and hurt — just as their love is beginning to bloom.
When Allegra’s ex suddenly reappears and Jack misunderstands the situation, their fragile new love nearly collapses before it truly begins. Fate has other plans: both Allegra and Jack end up sharing the same Uber on the way to Boston for separate career-changing opportunities. Forced into close quarters, they finally confront the feelings they have spent years hiding — and admit they have loved each other all along.
In the middle of the chaos, Jack proposes. The film closes with family, friends, dancing, and a joyous celebration of two people who found their way back to love — proving that sometimes the person you are looking for is the one you already knew.
Trailer
First Look
From the Writer / Director
Keishawn Blackstone
Founder · Akwire Media Group
“Jack in the Box was written from a very real place — the idea that love does not always arrive as something new. Sometimes love is someone you already knew, someone who saw you before the world changed you, before the heartbreak, the pressure, the ambition, and the walls we build around ourselves. As the writer and director, I wanted to create a romantic comedy that feels warm, funny, honest, and emotionally grounded. At its heart, this story is about two people who are successful in their own ways but still learning how to be vulnerable. Allegra represents the person who has worked hard to protect herself, while Jack represents the love that has been waiting patiently on the other side of fear. This film is about timing, friendship, healing, second chances, and the courage it takes to say what you really feel before life moves on without you. I wanted Jack in the Box to remind audiences that romance can still be playful, Black love can still be soft, and sometimes the person who makes you laugh the hardest is also the person who knows how to hold your heart the best. My hope is that audiences walk away smiling, feeling seen, and believing again in the kind of love that finds its way back home.”
Written & Directed by
Keishawn Blackstone
Produced by
Akwire Media Group
Distribution
Akwire Direct
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