Don Roos' "Happy Endings" is the kind of self-conscious puzzle picture in which characters behave in ways that serve the plot but in no way resemble things that actual human beings would be likely to do. A persistently bored-looking woman (Lisa Kudrow) is blackmailed by a young documentary filmmaker (Jesse Bradford) who claims to have information about an abortion she allegedly had as a teenager; to appease him, she offers her masseur-boyfriend (Bobby Cannavale) as a subject for the kid's movie, claiming he's really a sex worker who pleasures bored housewives.
Meanwhile, Kudrow's gay stepbrother (Steve Coogan) becomes convinced that his partner (David Sutcliffe) has been deceived by his oldest friend (Laura Dern), who attempted to conceive a child using his sperm. Elsewhere, gold digger Maggie Gyllenhaal beds first a young gay drummer (Jason Ritter) and then his earnest, nice-guy dad (Tom Arnold), who also happens to be loaded. We tread confidently through all this indie meshugas, assured that even though this story seems like a tangled Celtic knot, in the end its details will all interlock with a satisfying click, and we'll go home feeling a deeper connection to all of humankind, for 10 or 15 minutes at least.
That's how movies like "Happy Endings" are supposed to work. And the bummer is that, in the first 30 minutes or so, there's reason to think that Roos -- who wrote and directed the 1998 indie fave "The Opposite of Sex," as well as the more mainstream weeper (and better picture) "Bounce" -- might just pull off his ambitious goals. "Happy Endings" grapples with, among other things, the crazy messes that extended, ramshackle families can get themselves into. That's fertile ground for any filmmaker, particularly one who's assembled a cast as varied and as promising as the one Roos has here.
Kudrow gives a weirdly opaque performance: Her emotions waver mostly between smirky dismissiveness and regretful ambivalence, with not much in between. Even so, Cannavale, in a goofy-suave role, brings her to life in their scenes together. His character is intentionally cartoony at times (at one point he even dons a fake mustache), but somehow, we always believe in him, even when the script gives him a wild turn.
But this is a script that takes lots of wild turns, because this rickety structure needs to at least seem complex in order to hold our interest. Roos wants us to be surprised by what happens to these characters, and, in some cases, by the disparity between who we think they are and who they really are -- he wants to keep us guessing. But instead of showing us flawed people who have made occasional mistakes, he drops little bombs on us, turning likable characters, or at least benign ones, into people we never should have trusted in the first place.
We don't feel surprised at our own naiveté -- only duped. Here and there Roos inserts clever title cards that cue us how to feel about what we're seeing on-screen, in case we can't figure it out for ourselves. After we've been introduced to a major character, for example, one of those cards advises us, "Don't worry if you don't like her," and goes on to explain that her estranged husband is a compulsive gambler, which supposedly explains her lack of warmth, humor or assorted other generic human qualities. (It doesn't.)
Still, Roos' cast plows valiantly forward: Gyllenhaal gives some flirtatious, treacherous curlicues to an essentially inscrutable character. And Coogan puts his usual unblinking, unshakable comic timing to admirable use. But Arnold plays the character we end up feeling the most for, a widower well into middle age who takes a tentative chance on love even though it's 100 percent likely he's going to lose. Arnold's role is relatively small, even though he's probably the emotional center of the movie. He pours so much muted longing into his performance that, when he's on-screen, the picture seems like less of a stunt. More than any other performer in this contorted little picture, he's the one who makes us realize it's not how everything ends that matters -- it's the getting there we have to buy.