Every once in a while a love story appears that doesn’t shout, doesn’t rush, doesn’t bend itself into clichés — it simply breathes. I Thought You’d Never Ask is a slow pulse beneath the surface, a romantic short that captures the strange way time stretches when two people aren’t quite brave enough to meet in the middle. This isn’t a story of big gestures — it’s a story of the tiny ones we remember forever.
The film follows Lisa and Nathan through the delicate tension of almost-moments: the unspoken questions, the glances that hold an entire future, the fear of saying the wrong thing, or worse, nothing at all. When the magical twist arrives, it doesn’t feel like fantasy — it feels like what love sometimes gives us when we need it most: one perfect chance to become who we meant to be all along.
Jamal Trulove guides the film with a gentle hand, letting emotions simmer instead of explode. It’s romantic without being sentimental, wistful without losing hope — a portrait of what can happen when hesitation finally breaks. I Thought You’d Never Ask stands as a reminder that timing isn’t always ours to control, but courage is.
I Thought You’d Never Ask
Written & Directed by Jamal Trulove
A woman ages while waiting for her hesitant partner to propose—until a magical moment grants her a second chance. When Lisa meets Nathan, their spark is immediate. But as the years pass, Lisa feels pressure from time and societal expectations, fearing Nathan may never commit. Doubt from a close friend only amplifies her anxiety. Nathan tries to explain his hesitation, but Lisa struggles to see beyond her own insecurities. Just as their relationship reaches a breaking point, a single unexpected moment transforms everything.