As a gay man, I suppose I should be flattered by Friends with Money, since one of its messages seems to be that the more straight (or straight-acting) a guy is, the more horrible a human being he is. The film’s two good-looking straight guys (Jason Isaacs and Scott Caan) effectively represent the law firm of Callous, Unfeeling, Two-Timing and Greedy. But Simon McBurney, as a heterosexual married man so ambiguously effeminate that he regularly gets hit on by gay guys, is a devoted husband, a doting father and a sane, centered counterweight to the lunatics he’s surrounded by. Bob Stephenson, slightly overweight and shlubby, also turns out to be nice but somewhat helpless after seeming to be as much of a schmuck as the other straights, adding a corollary to the straight-equals-rotten equation: the prettier you are, the more pathetic you are.

Which is not to imply that writer-director Nicole Holofcener portrays women as much nicer or better than men. The three friends with money of the title are Jane (Frances McDormand), married to Saint Simon; Franny (Joan Cusack), married to mildly amusing Greg Germann; and Christine (Catherine Keener), married to Jason Isaacs of the ice-blue eyes and almost complete lack of empathy (perhaps he’s been playing villainous Lucius Malfoy too long in the Harry Potter franchise). Their poor single friend Olivia is played by Jennifer Aniston, providing a brave, unstarry performance as a former teacher, now a maid, with zero to negative self-esteem. An alternate title to the film could be Three Whining Kvetches and a Sad Sack.

Despite a lucrative career designing what she herself terms “hideously overpriced” clothing, McDormand’s Jane is an angry bitch, always on the lookout for someone to spew some venom on, from inattentive waiters to drivers who cut her off in traffic. Cusack’s Franny, so rich she and hubby Germann don’t know which charity to donate a spare $2 million to, tries to be nice to Aniston’s Olivia, generally with disastrous results (she sets her up with Scott Caan’s Mike, her personal trainer, who offhandedly and repeatedly humiliates Olivia, who is already busy humiliating herself by obsessively calling — and hanging up on — the married man she was last involved with). Keener’s Christine and Isaacs’ David are screenwriters in a mixed marriage: whereas she’s a needy human being who keeps accidentally-on-purpose tripping and hurting herself, he’s an unemotional cold fish who doesn’t even notice that his wife is in pain.

Whew! Complicated, no? And at its best, a complex character study, where at times each person on screen becomes more than the caricatures I’ve described. As in good fiction, and as in other Holofcener films (1996’s Walking and Talking and 2001’s Lovely and Amazing), I found myself shifting my sympathies as Friends with Money meandered along, noting that McDormand’s anger was part of an actual midlife crisis, and also suspecting that her expressed anger is what allowed McBurney to positively channel his own (a not uncommon dynamic with couples).

And while high-maintenance Keener became more sympathetic as the depths of Isaacs’ disregard were revealed, Holofcener also shows her character’s willed blindness. She and Isaacs are adding a second story to their Malibu home that will give them an ocean view from their bedroom but will block the views of all their neighbors, and conveniently oblivious Keener doesn’t understand why those same neighbors aren’t as friendly as they used to be. Ah, it’s a bitch to be rich and have such problems.

Olivia is a tougher case, psychologically and characterologically. Aniston is a better actress than many give her credit for; her blank stare and the drawn-out, dawning realization that she’s been screwed over yet again are heartbreaking each time they happen in Friends with Money. Yet she remains a mystery: why is this pretty, intelligent girl such a directionless doormat? Can’t she find any better friends than these women, whose wealth is a nagging tease to her? Is she a passive victim or does she bring her misfortunes on herself?

I understand that it’s not Holofcener’s style to provide easy explanations, or even excuses, for her shambling, neurotic characters. Her two previous films also featured self-destructive women and carelessly callous men, and all three films share an apparent lack of conventional narrative drive. Holofcener’s humor comes from the offhand remark and the all-but-unconscious gesture that define a character, like the final small smile on Catherine Keener’s face in this film. Keener is a Holofcener veteran of all three of her films, and she gets the writer-director’s sly humor perfectly.

Sometimes that humor is communicated to the audience, sometimes not. Interesting and quirky as Friends with Money can be, it’s not exactly entertaining. Like its characters, it’s often frustrating. But as an alternative to formulaic action-adventure and even to other teen-brained chick flicks, it’s worth a look.