Things begin to change when Jon finds himself blindsided by a love at first sight moment with Barbara (Scarlett Johansson), a slightly aloof "dime" who doesn't let Jon in so easily. The film's first half follows a sort of honeymoon period in their relationship and the unraveling of Jon's established patterns. For awhile, the energy of the trailers is sustained, and there's a smart, self-aware quality to the writing that lets Jon exist as something more than parody. Joseph Gordon-Levitt writes and directs here, in addition to his starring role, and the opening chapters prove he definitely has a flare for deftly drawn characters. There are slick, expert moves executed here in quickly establishing dimensional individuals. We get Jon immediately, and Barbara within minutes. All of this only makes the Don Jon's weak second half more of a frustrating letdown. After committing in full to the piggish, misogynistic qualities of Jon; embracing the hard R-rating in montages of porn and frank language, there's a shift towards redemption so forced, so overly practical, that it's near impossible to buy.
My theory on this is that Gordon-Levitt isn't really keen on being an unlikable character. He can only cast himself in the role of macho, porn-addled chauvinist for so long before sneaking the audience a sly smile and reminding the folks back home he's still the thinking girl's pin-up. So, in an admirable effort, Don Jon introduces a 'real woman' in Esther (Julianne Moore), a middle-aged lady who speaks her mind and confronts Jon on his public foibles. It's a great idea, but the more Esther becomes a presence, the weaker the narrative gets. Esther is a deus ex machina, a ghost from the morality machine who arrives on the scene to change Jon not via manipulation, but through experience, open-minded feminism, and a sexuality derived from something other than the pouty artifice of pornography. I should be all about this, and really, it's a smart step for a film to try. I wanted to believe the change. I admired what Gordon-Levitt was trying to do with his character's sexual salvation, the way the film forces him to start respecting women as something other than objects. But...I didn't believe it for a second.
Don Jon spends so much time pushing its character towards archetype; collecting his rage, making him confused and angry. All of this to the point that when the turn comes in the final act, it's so impossibly forced that it's seems like a sort of laughable, slapped-on fairy tale ending where it should be anything but. Our contemporary Don Juan is redeemed by respect and understanding, and as forward thinking as that might be, the film can't convincingly render it in the misogynistic world it seeks to imitate. Maybe if the film hadn't made Jon so consumed with the upkeep of his macho persona I'd be able to see the shift in character as a more natural progression. To his credit, JGL tries to introduce the shift earlier on in confession scenes, a slow pulling away from porn for a week here and there, etc; but the Jon always falls back, and each time he does he seems to fail harder, to resent and question things more. Consequently, after we've been shown what it looks like when Jon begins to lose faith or feels a change in his libido, the gentle turn away from porn-addled slacker narcissist towards gentle, loving, open-minded figure requires a suspension of disbelief. There were ways to make this work, but here Julianne Moore might as well be Jon's freckled fairy godmother.