Alan Mattli’s review published on Letterboxd:
Where Shithouse, in spite of its suspect eagerness to look past virtually all of its writer-director stand-in protagonist's flaws, struck me as putting forward some recognisable, broadly intriguing ideas that may have profoundly resonated with me at 22, Cha Cha Real Smooth is a shockingly vapid affair. Raiff is obviously very skilled at capturing the feel and tone of certain kinds of relationships – I like the bond he sketches between Andrew and his little brother in this one – but here, it's ultimately in service of nothing other than a cloying hagiography of an utterly unremarkable protagonist, who is, yet again, played by the writer-director himself. This was already a questionable proposition when Woody Allen did it in the 70s, but most of those movies either managed to strike some kind of emotional chord or to be consistently funny – neither of which Cha Cha Real Smooth is able to deliver on. Hardly anything about its story of a directionless college graduate seeking (and unfailingly receiving) validation whilst indecisively pursuing a crush he has on an engaged woman in her 30s rings true, or is presented with enough narrative conviction and stylistic heft to make it at least seem insightful, specific, and lived-in; and the stilted dialogue and uninspired delivery prevent the comedy from ever really landing. The result is a perfectly pleasant, wholly inconsequential movie, where the writer-director plays a character who is so charming and witty that Dakota Johnson almost starts having second thoughts about her impending marriage – and where nothing is ever quite substantial enough to lead to any interesting or surprising or thought-provoking or comedically memorable conclusions.