Film

Always Be My Maybe

Name: Always Be My Maybe
Genre: Romance, Comedy
Released: 2019
Cast: Ali Wong, Randall Park, James Saito, Michelle Buteau, Vivian Bang

Romantic comedy
Light-hearted

A smart romantic comedy about two people who loved each other once, drifted apart, and crash back into each other's lives when success pulls them in opposite directions. It's warm and funny without being sentimental, grounded in real friction between ambition and belonging. For anyone who's ever wondered what happened to that person.

TMDb rating

3.3

Should you watch it?

Watch it if you enjoy romantic comedies that find their laughs in awkward class friction, sharp banter between two proud people, and a love story that stays grounded in real history rather than grand gestures.

Skip it if you want a fast, glossy rom-com with a predictable rhythm; this one lingers in its quieter, more uncomfortable moments and does not hurry to reassure you.

What it asks of you: Just over an hour and forty minutes, it moves at an easy conversational pace, asking you to sit with small silences and watch two people circle each other without much fuss.

Not sure? Find tonight's pick in a minute.

If you liked this

Crazy, Stupid, Love.2011

A romantic comedy that actually understands how messy real attraction is, mixing genuine emotion with laugh-out-loud humour. It moves between multiple perspectives without losing its heart.

But The ensemble approach means no single story gets the depth some want; it can feel like it's solving problems with a montage.

Set It Up2018

Two people working toward their own goals accidentally fall for each other instead of the people they were supposed to pursue. It's got the same screwball energy and charm, with real chemistry between leads.

But It trades on romantic comedy conventions without reinventing them; if you've seen the blueprint, you'll see the joints.

Sleeping Dogs Lie2006

Flirting with darkness underneath, this indie romance asks whether some truths should stay buried. It's tender and awkward and genuinely surprising about what makes people tick.

But The subject matter gets uncomfortable on purpose; it's more interested in discomfort than reassurance.

Not sure tonight? Get a pick in a minute, starting from Always Be My Maybe

The wildcard

Something you would not have found on your own.

(500) Days of Summer2009

Both movies refuse the easy version of a love story, insisting instead on the friction between who we want people to be and who they actually are. Both are about two talented people discovering compatibility and incompatibility are sometimes the same thing.

A film that looks like a romantic comedy but is actually about how we construct narratives to make ourselves the hero of someone else's story. It's hilarious, heartbreaking, and utterly honest about desire meeting reality.

But The anti-romance stance means you spend the film frustrated with the main character; some find it punishing rather than enlightening.

Forgetting Sarah Marshall2008

A breakup comedy that's genuinely funny about disappointment and starting over, with chemistry that feels earned rather than assumed. The side romance has real stakes.

But Hinges on jokes that haven't aged flawlessly; some comedy reads differently than it did fifteen years ago.

Someone Great2019

Three friends on a road trip confronting love, mortality, and what you owe each other. It's got the same blend of comedy and something deeper, with real affection between its characters.

But Tonal shifts from comedy to something heavier don't always land smoothly; the pivot can feel abrupt.

Palm Springs2020

Two people trapped in a time loop have to actually work through why they're incompatible, rather than just falling into each other. It's clever, moving, and funny about the work relationships require.

But Leans heavy on sci-fi premise rather than grounded reality; if you want realism, this isn't it.

The Proposal2009

Forced proximity and secrets between two people who think they're too smart for romance. It's pure fun, and Sandra Bullock and Ryan Reynolds have genuine comic timing together.

But The plot is increasingly implausible; you have to let go of logic to enjoy it.

Master of None2015

Romantic, funny, achingly specific about how two people navigate timing and ambition. Dev and Francesca's love story gets real about why good people sometimes can't make it work.

But The show's rhythms are deliberately slow and indie; if you want plot-driven, you'll find it meandering.

Portrait of a Lady on Fire2019

Both understand that real intimacy comes from seeing someone as they actually are—flaws, ambitions, the works—and that understanding doesn't guarantee a happy ending. The connection isn't romance, it's clear-eyed tenderness.

A painter and her subject fall in love over weeks of portrait sessions in 18th-century France. It's sensual, quiet, and devastatingly about how deeply you can know someone and still lose them to circumstance.

But Deliberately paced, subtitled, and the ending is bittersweet by design; it refuses comfort or resolution.

Schitt's Creek2015

Same engine: two people from different worlds colliding, learning that love means adapting without abandoning yourself. Sasha and Marcus grow across one film; David and Patrick do it across seasons, but the emotional work is identical.

A wealthy woman and a musician reconnect when she crashes back into his life, forcing both to examine what they actually want. Over six seasons, it builds something warm and profoundly funny about accepting people as they are.

But Starts slow and sitcom-broad; the first season doesn't signal how good it becomes. Commitment required.