Rocky Papasano (Steve McQueen) is a jazz musician who is currently trying to secure work at a gathering of the musicians' union, making potential employers believe he is in great demand when actually he could use more work. He tells one of the officials to page him to make it sound as if he's almost fully booked, but it turns out there really is someone paging him, and she's Angela Rossini (Natalie Wood). Only she doesn't want to hire him, she here to tell him some sobering news: Rocky has made her pregnant, and she wants to know where she can get an abortion, preferably sooner rather than later...
Natalie Wood always suffered troubled romances in her films and Love with the Proper Stranger was little different. Here playing an Italian, and far more convincing at it that Steve McQueen is, Angie has to endure the pressures of her strict family who would not understand if she announced that she was going to get rid of her problem courtesy of a back street "doctor", and we can feel the burden of society weighing down upon her. She may be strong willed, but she is also scared, scared of what her family would do if they found out, scared of being an object of shame, and of any commitment when she doesn't have any emotional connection with the men in her life.
Rocky helps her out due to his guilt, but you don't have the sense that he would make a good enough partner for Angie even as he jumps through hoops to make sure she gets her wishes. Or at least, you don't for the first half of the film, which resembles the contemporary kitchen sink dramas that British cinema was churning out in its realistic depiction of issues that could be encountered by the general public. It is during this that Angie makes it clear she has no time for love because in effect she doesn't believe it exists, having seen childhood sweerthearts grow up together and, in her mind, become miserable with each other and either divorce or put up with their dejection.
Angie doesn't want to end up like that, but the alternative, spending life alone, is not something screenwriter Arnold Schulman is prepared to consign her to. Therefore, the plot hinges around the abortion sequence, where Rocky takes Angie to see the "doctor", but the circumstances are so seedy that coupled with her guilt the girl cannot go through with it. Not that the censors would have allowed Natalie Wood to get an abortion in 1963, but the fact that the filmmakers to have her consider it was quite daring for the time, and makes for edgy viewing. But then there's that second half, where once the worst is over and she's keeping the baby, a different tone makes itself plain.
This second half is altogether lighter, and with a few more goofy gags could easily have been part of a light romantic comedy of the kind that Wood might have starred in without any controversy. The key scene is where Angie goes to a dinner at the apartment of one of her suitors, the doughy and clumsy yet sweetnatured Anthony (Tom Bosley in his film debut), and his family are there, including his beatnik sister who we're meant to chuckle at as she shoots down the traditional idea of love and relationships in flames. She's a cartoon character intended to make Angie realise what an old grump she's been, and naturally it works to the extent that Anthony gets left behind in the dust and Rocky is the man she chooses as her potential suitor - if only they could get along with each other. So Love with the Proper Stranger is more conservative than it initially appears, and depending on your outlook you might find yourself appreciating one half more than the other. Great final shot, though. Music by Elmer Bernstein.