In an unnamed Midwestern American city, the lives of two urban, middle-class couples become tangled in a web of deceit and discontent as they pursue their own versions of happiness. Jerry, portrayed by Ben Stiller, is an obnoxious, flirtatious theater instructor who is married to Terri, played by Catherine Keener, a writer feeling alienated and unsatisfied with Jerry's overbearing masculinity in their intimate life. A seemingly routine dinner with Mary, a writer friend of Terri's played by Amy Brenneman, and Barry, a hapless business executive brought to life by Aaron Eckhart, reveals the cracks in their relationships. Mary shares her thoughts on writing a column for a local newspaper that explores the conflicts of couples, while Barry dismisses the struggles of others as insignificant.
Post-dinner, Jerry makes a bold move by discreetly inviting Mary out on a date, which she reluctantly accepts, fueled by her dissatisfaction with Barry. Meanwhile, Terri, after visiting an art gallery, embarks on a clandestine romance with Cheri, played by Nastassja Kinski, a lesbian gallery worker, who offers the emotional and physical satisfaction that Jerry fails to provide.
Adding to the chaos is Cary, a conniving doctor friend of Barry’s who preys on vulnerable women, reveling in their emotional turmoil. He persuades Barry to embrace a non-monogamous lifestyle, despite Barry's futile attempts to hold onto his marriage.
During Jerry and Mary's hotel rendezvous, Jerry's self-esteem plummets as he fails to perform, leading him to lash out at Mary, blaming her for his impotence. This misogynistic reaction prompts Mary to end their affair. Weeks later, a clueless Barry brings Mary back to the same hotel, unknowingly stirring up painful memories.
As friendships fray, a gym meet-up between Jerry, Barry, and Cary devolves into a shocking conversation when Cary recounts a dark story from his past, leaving Jerry and Barry in stunned silence. Pressured by Barry to share his own best sexual experience, Jerry coldly reveals it was with Barry’s wife, a remark that leaves them both speechless.
Conflicts boil over as Barry confronts Mary about her affair, coinciding with Terri discovering Jerry’s betrayal during a bookstore trip. Both couples express their dissatisfaction, with Terri carelessly disclosing her relationship with Cheri, showing no remorse for her infidelity.
Jerry, infuriated by Terri's affair, accosts Cheri in the gallery, only to be met with indifference. As the storm of betrayal and heartache unfolds, both couples go their separate ways. Terri moves in with Cheri, though their emotional dynamics prove complicated, while Jerry continues his liaisons with his theater students. Barry descends into despair, grappling with impotence, and Mary, now living with Cary, finds herself coldly treated, despite being pregnant. In a haunting finale, as Mary lies in bed with Cary, she realizes her new relationship is even more suffocating and unhappy than her previous one, marking a bitter conclusion to their search for fulfillment.
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