Talk about ambitious plotting. Mamie (Lisa Kudrow) and Charley (Steve Coogan), once teenaged stepsiblings, shared an affair and an unwanted pregnancy. As adults, Charley is now gay and Mamie, who gave the child up for adoption, is being blackmailed by wildcard young filmmaker Nicky (Jesse Bradford), who knows the identity of her now-grown son. Javier (Bobby Cannavale), a Mexican immigrant masseuse involved with Mamie, becomes ensnared in the comic extortion. Charley and Gil (David Sutcliffe), a picture-perfect gay couple, wrestle with confronting lesbian best friends Pam (Laura Dern) and Diane (Sarah Clarke) about the DNA of their own young son, who may be the surreptitious product of Gil’s own sperm donation, which supposedly didn’t take. They’ll be faced with an unexpected revelation that tests them both. Jude (Maggie Gyllenhaal), a free-spirited young woman who inadvertently ends up fronting a rock band, sleeps with closeted gay drummer Otis (Jason Ritter) before moving on to an affair with his wealthy father Frank (Tom Arnold). But is Jude really in love or is something else at work?

The ensemble is uniformly fine even when writer-director Don Roos puts them through the plot’s criss-crossing contrivances, frequently accompanied by onscreen text explaining their motivations, that’s sometimes funny, sometimes not. But this is an actor’s show all the way. Jesse Bradford seems liberated by Nicky’s recklessness while Lisa Kudrow astonishes as a woman uncomfortable in her own skin, all nervous tics and untapped emotion, dispelling any residue from her TV sitcom signature. She creates a most believable modern woman who finds herself in an extreme situation, and Kudrow wisely lets Mamie’s confusion all hang out here, at times timid and others a ball of confrontation.

Bobby Cannavale, the charismatic star of The Station Agent, presents masseuse Javier as a comically exotic man of secrets, whose real colors show when faced with a startling betrayal. And Laura Dern’s protective, lesbian best friend packs quite a wallop in the film’s best scenes, each involving revelations of disease and adultery. But it’s Maggie Gyllenhaal who may just steal the show here with a performance of sexual abandon, beguiling a winning Tom Arnold with casual nudity and the power most young women dare not use on older men. A portrayal peppered with impressive singing that feels initially raw and amateurish and later lived-in and graceful.

Despite the considerable acting on display, something feels slightly amiss in Happy Endings. Perhaps it’s because Roos, the talented and observant director of The Opposite of Sex and the underrated Bounce, writes such off-beat characters that we need time to get to know them, to penetrate them. And in this smattering of messy lives, we don’t get too close to anyone though we’re certainly, at times, affected by each. The whole just seems a tad underwhelming though it’s certainly fun to watch unfold. The film never has as strong an emotional impact as Kudrow and Dern reach in their best moments.

Roos is after the idea that to be happy—in essence to have happy endings or beginnings—is about finding personal truth. Eschewing the fairy-tale aspect, the film pulls no punches in taking its characters where they logically should go. If there’s a happy ending of sorts near the film’s climax, there are also a few decidedly mixed ones. Gyllenhaal’s Jude, in particular, arrives in a place of new womanhood after a trial by fire, which as much as the character downplays, affects her deeply. You don’t know where this film is going and Roos cleverly keeps surprising.

Happy Endings is well-directed, well-performed diversion with enough energy and laughs to make us want for more. It has provocative characters, a refreshing take on sex and attraction, some new dynamics on gay adoption, a few things to say about May-December love, how the material and emotional can tangle, and a sweet moment of recognition between two band mates near the film’s close. If the prototype for this type of film is Robert Altman’s masterpiece Short Cuts, then Happy Endings falls short of that film’s depth and substance. On its own, it’s an entertaining slice.