“To Rome With Love” follows four different concurrent but unrelated plotlines taking place in the Eternal City.
American tourist Hayley (Allison Pill) falls in love and becomes engaged to Italian pro bono lawyer Michelangelo (Flavio Parenti) while spending a summer in Rome. Her parents Jerry (Woody Allen) and Phyllis (Judy Davis), fly to Italy to meet her fiancé and his parents. Michelangelo’s father Giancarlo (Fabio Armiliatio) works as a mortician and washes up when he comes home from work each day. Jerry happens to hear Giancarlo’s beautiful operatic voice while the latter sings in the shower. As a former (and admittedly avant-garde critically-reviled) opera director, Jerry feels inspired to bring Giancarlo’s gift to the public. Although Giancarlo protests that he sings for himself and doesn’t want to go professional, Jerry pushes the issue until Giancarlo agrees to audition in front of a room of opera bigwigs. Outside the safety of his shower, Giancarlo’s confidence abandons him. His voice cracks on several easy notes, and he is humiliated. Michelangelo, who attended the audition too, accuses Jerry of using his father to achieve some level of fame for himself. It suddenly occurs to Jerry that Giancarlo, like most people, sings the most confidently when he has some measure of privacy. In Giancarlo’s case, he performs best in his shower. Giancarlo, naked but for a towel, premieres at the Teatro dell’Opera di Roma. Jerry has built him a shower onstage, and Giancarlo sings as he washes. The opera attendees love his strange performance, so Jerry and Giancarlo decide to stage Pagliacci, shower and all. Again, Giancarlo’s rich voice mesmerizes the crowd, and he receives rave reviews. He decides to retire from opera singing, because he prefers working as a mortician and spending time with his family.
Newlyweds Antonio (Alessandro Tiberi) and Milly (Alessandra Mastronardi) move from their rustic hometown to Rome because Antonio’s posh uncles have offered him a job in their family’s business.
The couple check into their hotel, and Milly decides to pop down to the salon to fix her hair. When the concierge informs her that there’s no available appointments, Milly decides to go to a nearby salon but she forgets the directions and becomes hopelessly lost. When she tries to call Antonio, she accidentally drops her phone through the slats of a sewer grate. Defeated, Milly eventually sits down on the edge of a fountain. When she looks up she sees one of her favorite actresses, Pia Fusari (Ornella Muti), about to shoot a scene. Pia invites Milly to watch her film, and Milly becomes even more excited when she learns her celebrity crush Luca Salta (Antonio Albanese) is also in the film. After the scene wraps, Pia introduces Milly to Luca, who invites Milly out to lunch with him.
Meanwhile, Antonio is back at their hotel. He’s desperate to find Milly, because his relatives will soon arrive to take them out to lunch. Someone knocks at the door, and, thinking that Milly has returned, he rushes to answer it in his underwear. Anna (Penelope Cruz), a prostitute, bursts into his room. She has mistaken him for a client, and she refuses to leave until they have sex. Anna wrestles Antonio to the bed, but his relatives interrupt them before anything untoward happens. His uncles mistake Anna for Milly, and when it becomes too complicated to explain the truth, Antonio goes along with the ruse. He convinces Anna to pretend she’s Milly for the afternoon. First Antonio’s uncles take him on a private tour of the Vatican. While admiring the Sistine Chapel, Antonio’s aunt asks, “Can you imagine working on your back like that?” Anna replies, “I can.” Later the group dines at the same restaurant that Luca takes Milly. Antonio seethes with jealousy as Luca flirts with Milly. Lastly, Antonio’s uncles and aunts take him to a fancy party so he can meet important Italian dignitaries. Antonio has nothing in common with the men his uncles introduce him to; coincidentally, most of the male guests are Anna’s clients. Anna and Antonio go for a walk in the garden, and Antonio talks about how pure and good Milly is. When Anna finds out he was a virgin before he met Milly, she seduces him in the bushes.
Luca brings Milly to his hotel room. He also tries to seduce her. Luca’s compliments charm Milly, but she doesn’t know if she can cheat on Antonio. She goes into the bathroom to get some perspective, and she ultimately decides to have sex with Luca. As Milly strips, a man with a gun jumps out of the shower. He takes Milly into the bedroom and demands that she and Luca give him their money and their jewelry. Suddenly, Luca’s wife and her private investigator begin banging on the hotel room’s door. Mrs. Salta wants photographic proof of her husband’s indiscretions, and the prospect of divorce frightens Luca more than the burglar. Milly and the burglar climb into bed and fool Mrs. Salta into believing the hotel room is theirs while Luca hides in the bathroom. Once his wife has left, Luca runs off, and the burglar begins flirting with Milly. She has sex with him instead. When she returns to the hotel room, she and Antonio decide to return to their rustic hometown. They make passionate love before checking out.
Leopoldo lives a mundane life with his wife and two children. The best part of his day is watching his boss’s beautiful secretary Serafina walk around the office. Inexplicably, he wakes up one morning to discover that he has become a national celebrity. Paparazzi document his every movement. Reporters ask him what he’s had for breakfast, if he wears boxers or briefs, whether he thinks it will rain. Suddenly Leopoldo becomes the boss at his company, and Serafina sleeps with him. He begins dating models and attending fancy movie premieres. The constant attention wears on him, though. One day, in the middle of interviewing Leopoldo, the paparazzi spot a man “who looks more interesting,” and they abandon Leopoldo. At first Leopoldo welcomes the return to his old life. But one night he breaks down when no one asks for his autograph; he pulls down his pants to show people he’s wearing boxers and screams that he has toast for breakfast. Leopoldo has learned that life can be monotonous and wearying whether one is a celebrity or a normal man. Still, it’s much better to be a weary celebrity than it is to be a weary regular man.
John (Alec Baldwin), a well-known architect, and his wife are visiting Rome with friends. John lived there some thirty years ago, and he’d rather check out his old haunts than go sightseeing with the others. John meets Jack (Jessie Eisenberg), an American architecture student, while he’s looking for his old apartment building. Jack invites John up to the apartment he shares with his girlfriend Sally (Greta Gerwig). Sally tells Jack that she invited her best friend Monica (Ellen Page) to stay with them while she recovers from a rough breakup. According to Sally, Monica gives off a sexual vibe that drives men crazy. John predicts Monica will bring trouble, but Jack can’t imagine why he would be attracted to his girlfriend’s best friend. Monica arrives, and one of her first conversations with Jack is about her intense sexual relationship with a lingerie model. John pops up behind Jack based on how inexplicably John appears, he is either Jack’s future self or Jack’s conscience personified and tells him that Monica is hitting on him. Because Sally has classes, she often asks Jack to show Monica around Rome. Monica impresses Jack with her knowledge of literature and art. John often calls bullshit when Monica quotes a historian or someone Intellectual “She knows one line from every poet.”
Even though John cautions Jack against cheating with Monica, he cannot help but succumb to her charms. Sally sets Monica up with one of their friends, and Jack is jealous of their relationship. One night he and Monica decide to cook dinner for Sally and her boyfriend. They flirt more and more until Jack summons the courage to kiss Monica. She returns his passion, and they go down to his car to have sex. The next morning they decide Jack should wait until Sally finishes her midterms for Jack to break up with her. The trio go out for lunch after Sally’s finals, and when they’re alone Jack tells Monica he plans to dump her that night. They make plans to travel to Greece and Sicily together. Suddenly, Monica, an actress, receives a phone call from her agent. She can barely contain her excitement as she tells Jack that she’s been offered a role in a Hollywood blockbuster. She will film in Los Angeles and Tokyo for the next four months. At the drop of a hat, Monica becomes completely focused on preparing for the role. She forgets about traveling with Jack, and he realizes how shallow she is. John and Jack walk back to the Roman street corner where they met and part ways forever.
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