Connor Mead (Matthew McConaughey) is the consummate player. A photographer of world renown, he arrives at his latest shoot just in time to snap the picture—the camera, pretty girls in underwear and spotlights already in place and waiting. He calls the shot perfect, then heads off to arrange the next, a still-clothed pop star (Stephanie Oum) in need not only of stripping for her magazine cover but also—mere minutes later—Connor’s legendary sex.
Yes, Connor’s life is pretty perfect. Which is why he must be taught a lesson. Seeing as he lives inside a movie called Ghosts of Girlfriends Past, you might imagine who shows up to administer that education. You might also anticipate its limits, given that it is premised on Connor reckoning with women with designations like “Slapping Brunette” (Toni Saladna), “Ice Cold Blonde” (Gina Gesamondo), “48 Seconds Bar Woman” (Lauren Tangard), and “Bar Twins” (Kimberly and Ashley Carvalho).
Incredible, but true: this movie is as retarded as it sounds.
Connor’s change is occasioned by his younger brother Paul’s (Breckin Meyer) wedding to Sandra (Lacey Chabert). Connor arrives full of himself, determined to put the kibosh on Paul’s impending bliss, telling anyone who asks and even those who don’t how much he despises marriage the obsolete concept (and not because it’s premised on treating women as property). “I wish I could believe in all this crap,” he lies, “But I am condemned to seeing the world as it really is. The truth hurts, baby.” The rest of the wedding party repeatedly responds to such dated nuggets of swinging wisdom by looking away or rolling their eyes, but all put up with him because Paul insists he’s a good man deep inside. Right.
The brotherly loving is offset by a wearisome supporting cast: the gratingly neurotic Sandra brings along her doting father, the buzz-cut Sergeant Volkom (Robert Forster), as well as her mother, voluptuous Vondra Volkom (Anne Archer). Connor immediately guesses she’s divorced (because “No married woman this age keeps her form this fine!”) and makes a definitively yucky pass (when she notes that “spooning is nice,” he counters that it’s “not as nice as forking”). This in addition to his efforts to bed the one of three bridesmaids he hasn’t yet; conveniently color-coded—one blond, one brunette, one redhead—these girls are all drearily… um, how to put it? stupid, shallow, and banal. Connor draws something of a line here (he doesn’t want to sleep with the bridesmaid his brother has already slept with, because, he explains, “I don’t like to cross swords”), but really, who cares?
At least she doesn’t have to meet Connor’s now-dead Uncle Wayne (played by Archer’s Fatal Attraction husband Michael Douglas, in poofty hair and Robert-Evans-style tinted glasses). Playing Marley in the Scrooge plot, Wayne walks his nephew through memories of their early cavorting. When, as a dreadfully shy high school student, Connor has his heart broken, he resolves never to “feel this way again” by adopting Wayne’s prehistoric worldview (“Dames are like horses, they spook easy,” “Every dude with a johnson has got a chance,” etc.).
Wayne doesn’t appear to feel bad that he turned deep-inside good Connor into a wholly prosaic philanderer, but he does warn that his late-in-life loneliness may not be the best end to pursue. And so he sets his nephew on a course of reform, led at first by the Ghost of Girlfriends Past, eternally 16-year-old Allison (Emma Stone). Landing in Connor’s bed with braces and circa-1982 foofy skirt and frizzy hair, Allison reminds him of the many girls he’s had, including the one he really and truly loves in spite of himself, Jenny (Jennifer Garner, who is, like McConaughey, too old to be playing in these barely-post-adolescent fantasies).
Now a doctor (i.e., successful and smart), Jenny also happens to be at the wedding as Sandra’s maid of honor, which means she and Connor can clash in so-called real time as well as during his ghostly visitations: in their shared past, she dances with another boy at prom and so sends Connor on his egregious life course. She’s also the central knot Girlfriends can’t untangle, which is to say, Jenny shows up in his past, resent, and future visions. The problem is, after the film spends long minutes revealing Connor’s past exploits, it’s pretty much stuck. The Present Ghost is a spectral version of his actual ultra-professional assistant Melanie (Noureen DeWulf) and the Future Ghost an unnamed, voiceless apparition in a long white gown (Olga Maliouk): neither of their tours of Connor’s options is remotely interesting, because once Jenny’s introduced in the “past” segment, well, his course is set. The other stories are just filler, while he figures out how to get back with the girl he really wants.
The knot of Jenny is this: she and Connor have known each other since they were cute little kids running around the back yard in slow motion, and even admitted to moments of infatuation and/or true love, but after a disastrous one-night-together, she has promised herself not to fall for the “Connor Mead” treatment again. It’s never clear why he needs the ghosts business to realize that he was wrong on this count, as he seems pretty much resigned to his fate from the moment he spots Jenny flirting with the doctor (Daniel Sunjata) Sandra’s set her up with.
Even with its conclusion so plainly foregone, Ghosts can’t seem to help itself. Blundering from one bad joke set-up to the next, mostly at the girls’ expenses—a strange choice, given that Connor is supposed to be student here—it submits frequently that Connor deserves to be saved by Jenny. But it never shows how or why she should bother with him.