Jesse Hassenger’s review published on Letterboxd:
Look, I can't feign surprise that a Netflix Original, especially one commissioned as such, has the indistinct and low-rent look that doesn't even count as TV-like anymore because so many TV shows look so much better than this, nor should I be all that irritated that so many people have given this a pass because Ali Wong and Randall Park are funny and charming. It's basically a sitcom miniseries or a hipper Lifetime movie. Why would I pay attention to this, and not one of 47 Hallmark Channel movies that will be made similarly available this December?
But guys, I like romantic comedies, I like Ali Wong, I like Randall Park, and I even admit that I like being able to watch a facsimile of a new-release movie on a Saturday night after my kid is in bed without hiring a babysitter. So it's still disappointing that this movie sucks! And it really does suck!
It's about the passage of time and has NO IDEA how to create a sense of the passage of time (the 16 years in between the freshman-year material and the present-day material feel like they've actually taken about eight months, and not just because Wong and Park are playing below their real ages in both timelines). It positions itself as a little quippier and wittier than your average rom-com, but the jokes feel plugged-in, not just because they're often weak (though they are!) but because they often look ADR'd. I'm not sure if they actually were, because all of the staging is so clumsy that it's impossible to tell what was fixed in post and what was just always kinda bad, on purpose. There's dead air around jokes that might sound funnier if they were fired off quickly. The movie tells you the characters are a certain way without relying on the performers to show it. As long as I'm complaining: Wong is not very good in this! I've really enjoyed her stand-up but her reaction shots are hammy and her walk-and-talks are awkward-looking. I don't think it's necessarily her; Park has been better in almost everything else I've seen him in, too.
The movie's catchy title describes a premise that doesn't even really apply to this movie! (If you have sex with your best friend at 18, and then don't see them for nearly two decades, was that person "always" your "maybe"? Or was that person "once" your "kinda"?)
It's kind of mind-boggling that after this many at-bats, Netflix can't even seem to accidentally produce a good romantic comedy. No matter how much reinforcement they're getting saying that this kind of shit is everything.