In the summer of 1969, a sensitive, X-rated studio movie called “Midnight Cowboy” proved a box office surprise, upending norms when it won best picture at the Oscars. Flash-forward to this year, and the screwball Stripperella comedy “Anora” unexpectedly repeated that coup, demonstrating once again that the industry is capable of looking beyond stereotypes where sex workers are concerned.

Now comes “Summer of 69,” a risqué coming-of-age movie that manages to be both retrograde and refreshing in its portrayal of an awkward Catholic school student (Sam Morelos) who hires an inspirational pole dancer (Chloe Fineman) to help boost her confidence in the “bedroom department.” It’s a throwback to decades of raunchy-sweet sex comedies, from “No Hard Feelings” to “The Girl Next Door,” while also being somewhat progressive in that this time, it’s a girl who’s taking charge.

The problem — and hardly an insignificant one — is that however funny...