But a new clip from the film proves that he's met his match in the form of Barbara, played by Scarlett Johansson.
Everything seems to be going to plan as the photogenic duo bump into an apartment doorway while kissing passionately.
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Getting hot in here: Scarlett Johansson and Joseph Gordon-Levitt star as lovers in Don Jon, which opens in theaters September 27
'I don't know your friends. I wanna meet your family,' she adds.
That brings things to a screeching halt for Jon (Gordon-Levitt) - 'Why would, uh - our families?' he stammers in reply.
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'Don't you think it's always better when it means something?' Barbara coos.
The clip ends with Jon standing stunned as Barbara slams the door shut on him with just two words: 'Call me!'
Rejected: Jon's efforts to get Barbara in bed are rebuffed, much to his dismay
After meeting romance-obsessed Barbara, he begins to pursue a genuine relationship with her - but that's jeopardized when she discovers his dirty digital secret.
'I thought the idea of a guy, who watches too much pornography, and a young woman, who watches too many romantic Hollywood movies, was a hilarious way to ask the question: How do the different kinds of media we consume impact our lives and our love lives?' Gordon-Levitt told the Huffington Post in March.
First try: Don Jon is Gordon-Levitt's directorial debut
'The reason I think the movie works is because we manage to find a really great tone that balances an unusually bold honesty with a really fun and entertaining comedy. That is a tone that you won't really to be able to see that on the page,' he said.
'You have to trust that the actors and everybody else are going to bring that. This wouldn't have happened at a studio.'
All of the lights: Gordon-Levitt arrives at the red carpet of the 2013 MTV Video Music Awards, held in New York City on August 25
'The self-assured helmer shows genuine affection for his characters, balancing their openly satiric qualities with a disarmingly sincere human center,' wrote Variety's Peter Debruge in January.
Other critics noted the sharp-eyed cultural messages woven though Gordon-Levitt's raunchy, comedic script.
The film, which is Gordon-Levitt's directorial debut, opens in a wide release on September 27.
Looking good! Johansson poses at Marvel's photocall on July 20 at Comic-Con, held in San Diego, California
Funnyman: Gordon-Levitt speaks onstage during the 2013 MTV Video Music Awards at New York City's Barclays Center on August 25
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