- John and Molly, a divorced middle aged man and a single mother meet at a friends party and start up a small relationship, all John has to do now is meet Molly's son... Cyrus
- With John's social life at a standstill and his ex-wife about to get remarried, a down on his luck divorcé finally meets the woman of his dreams, only to discover she has another man in her life - her son. Still single seven years after the breakup of his marriage, John has all but given up on romance. But at the urging of his ex-wife and best friend Jamie, John grudgingly agrees to join her and her fiancé Tim at a party. To his and everyone else's surprise, he actually manages to meet someone: the gorgeous and spirited Molly. Their chemistry is immediate. The relationship takes off quickly but Molly is oddly reluctant to take the relationship beyond John's house. Perplexed, he follows her home and discovers the other man in Molly's life: her son, Cyrus. A 21-year-old new age musician, Cyrus is his mom's best friend and shares an unconventional relationship with her. Cyrus will go to any lengths to protect Molly and is definitely not ready to share her with anyone, especially John. Before long, the two are locked in a battle of wits for the woman they both love-and it appears only one man can be left standing when it's over.—Fox Searchlight
- John is a sad-sack of a man, that state which he wears openly on his sleeve. This phase of his life led to the dissolution of his marriage to Jamie seven years ago, she who left him. That depressed perspective takes another hit when Jamie, who he still treats as his primary confidante, tells him that she is getting remarried to a man named Tim. To get John out of his funk for at least one night, Jamie and Tim invite him along with them to a party where they encourage him to socialize with the plethora of fun women who they promise will be there. Against the odds, John, openly lamenting about his depressed state and the reason why, does make a connection with beautiful Molly. What Molly likes about John is how open and honest he is about himself and what he wants, which leads to John not following the regular social conventions of dating in his pursuit of her. Molly, while seeming to like John, is in full non-disclosure about something about her own what she states complicated life that is making her keep her distance to a degree. John does find out that that complication is Molly's unusual relationship with her twenty-two year old son, Cyrus, who still lives with her and upon who she dotes. Molly's treatment of Cyrus is because of his sensitivity about life in general. However, John finds that Cyrus, truly an adult in many respects, openly welcomes him into their house and into their lives. John eventually finds that what Cyrus portrays on the surface and what he is truly feeling and thus manipulating are two different things, Cyrus whose every action is in an effort to get John out of their lives while making it look like it's all John's fault. As John is truly falling in love with Molly and she for him, John has to decide if Molly is worth the battle with Cyrus, and if so how best to handle the situation in what could easily be Molly needing to take a side, which more than likely would be on her son's.—Huggo
- Jamie (Catherine Keener) informs her ex-husband John (John C. Reilly) that she is getting married. Even though they have been apart for seven years, the news devastates John, who was already depressed. At a party the next night, John gets more and more drunk until he ends up urinating in the bushes, where Molly (Marisa Tomei) strikes up a conversation. Molly goes back to John's house but leaves during the night, after they have had sex. Molly returns for dinner the next night, and again leaves after they have had sex. John follows her to her house and falls asleep in his car. The next morning, he approaches the house and meets Molly's 21-year-old son Cyrus (Jonah Hill). Cyrus invites John inside and makes friendly conversation with him. Molly is startled to see John in her house when she returns, but the trio have dinner together. John is unnerved by the unnatural intimacy between Molly and Cyrus.
The next morning, John cannot find his shoes, which he had left in the living room. Through the day, he gets increasingly disturbed by their disappearance and starts to worry that Cyrus is messing with him. He ropes Jamie into meeting Molly and Cyrus, in order to appraise his paranoia. Jamie finds Cyrus sweet, if a little overly intimate with his mother. Relieved, John returns for another night at Molly's home. As they begin to have sex for the first time in her house, Cyrus screams in his room, and Molly runs to comfort him. She does not return to John, who goes out looking for her in the middle of the night. He encounters Cyrus holding a large kitchen knife, allegedly making a snack. Cyrus says he had a night terror, and that Molly has gone to sleep. He then advises John to back off on the relationship because he is scaring off Molly. John leaves a note for her and goes home. In the morning, Cyrus sits Molly down and tells her that John had confessed to him that she was coming on too strong. When she presses Cyrus for details, he explodes in a tantrum and storms off, checking through the window to make sure that she is upset. When Cyrus finally comes home, he explains that he has rented a room and will be moving out. After a few happy days alone together, John decides to move in with Molly.
One night, as they begin to have sex, Cyrus surprises them and says that he has had another panic attack and wants to return home. John confronts Cyrus privately, and Cyrus admits that he has been deliberately sabotaging their relationship. He moves back home, and John remains wary of him. The night before Jamie's wedding, he warns Cyrus not to cause trouble. At the wedding, however, Cyrus is hurt when he sees how the event stirs romantic feelings between John and his mother. Drunk, he confronts John in the bathroom and attacks him, yelling that John will not take his mother away from him. As John defends himself, they spill out of the bathroom, into open view. Cyrus makes it look like John attacked him. John advises Molly to open her eyes, and storms off furious.
Later, Molly believes John's explanation, but John will not continue the relationship, convinced that Cyrus will sabotage it and that he will end up alone in a few years. He moves into a cheap apartment. Molly confronts Cyrus about his behavior, and describes how unhealthy their intimacy has become. Cyrus reconsiders his position and visits John, begging him to come back. John opens his door to see Cyrus crying, and they reconcile. John takes Cyrus home and decides to continue his relationship with Molly.
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