Drinking Buddies is that thing that they say doesn't get made much anymore—a well-executed, charming, effective, and plausible romantic comedy.
As is frequently the case with romantic comedies, a large part of the film's success comes down to the star. Olivia Wilde is simply incandescent. Her Kate—a secretary/administrator at the brewery—is goofy, competent, flirtatious, funny, and oh-so-subtly, irresistibly vulnerable. The rest of the cast is very fine as well; Luke (Jake Johnson), a brewery worker, balances a pleasingly playful bad-boy edge with a sense of actually having a moral compass—he is, thankfully, neither a nebbish nor an asshole. Chris (Ron Livingston), avoids stereotype too. He's an awkward nerdy guy ("possibly on the Asperger's spectrum" as he says), but he's neither desperate nor the butt of the film's jokes. The fact that Livingston is able to portray him as not absolutely head over heels in love with Kate, and make that ambivalence convincing even after we've seen Olivia Wilde in a bikini, is an acting feat of no small order.
Chris's ambivalence is subtly linked to class. He's more of a yuppie intellectual than Kate is—into John Updike and poetry and hiking and Camus. That difference, the movie suggests, actually matters. This cuts against Chris Orr's assertion in The Atlantic that we've moved past the point where class can function as a barrier in romcoms. Nor are the film's other obstacles especially decadent or desperate—no zombies or hookers or telepaths. Instead, there's just that old, trusty complication, used in everything from Kiss Me, Stupid to 16 Candles to The Sure Thing: significant others.
Like Kate, Luke has a significant other, Jill (Anna Kendrick), a special-education teacher who is pushing him to marry. Kate and Luke's flirtation, then, is doubly hemmed in, and doubly uncomfortable. Infidelity is, by some accounts, one of our last moral absolutes. Most people would say, at least in theory, that cross-class couples, or interracial couples, or even (a la Harold and Maude) intergenerational couples are okay; you can root for those couples to get together at least, with just a little narrative prompting. But there aren't many folks who are going to root for the protagonists to cheat, unless the significant others in question are presented as thoroughly unlikable or obviously unsuitable. And while neither Chris nor Jill is a paragon, they're both likable and sympathetic, not malevolent shells to be crushed up in the remorseless grinding of the plot.
What's important in your romcom isn't that the storyline follow the same storyline that every other romcom has followed ever. What's important is that it's romantic and that it's funny.
Still, the chemistry between Luke and Kate is sweet enough, and real enough, that you're not exactly rooting against them either. Luke's faux horror as Kate strips out of her clothes to run into the ocean in the middle of the night; or his much more real horror at discovering that she has still, weeks (months?) later not taken down her birthday party decorations; or the way Kate, quietly, and with a look somewhere between tenderness and pain, lies down beside him while he's sleeping—those are lovely moments, only heightened by the awareness that they may be, might be, shouldn't be crossing over a line. Kate and Luke are appealing; they're good together; we'd like to see them together—and we aren't sure we will. That's how a romcom is supposed to work, damn it.
It's possible that some folks might argue that the narrative here isn't sufficiently formulaic to strictly qualify as a romantic comedy. I would disagree, though. On the contrary, the final virtuoso silent scene, which moves from dour hopelessness to anticipation to charm-your-socks-off-flirtation, culminating in an intentionally phallic banana being tossed in a trashcan, seems like it couldn't be much more explicit about the movie's commitments. What's important in your romcom isn't that the storyline follow the same storyline that every other romcom has followed ever. What's important is that it's romantic and that it's funny—and if that means wrong-footing your expectations on occasion, so much the better.
I don't know that I'm quite ready to rank this with His Girl Friday or Say Anything in my personal pantheon of favorite romcoms. Still, the dialogue was consistently witty (I think the high point may have been Chris's quip about not being sure whether or not the cello in the indie rock band he was recording was supposed to be ironic), and I even fell in love a little bit. Drinking Buddies is evidence, then, that romcoms aren't dying out because our society has moved past them. All you need to make one work, it turns out, is talented actors, a good director (that would be Joe Swanberg), and a screenplay that's clever enough to know that sometimes you have to take an unexpected turn or two to deliver on your genre's pleasures. Those attributes are rare at the best of times, and seem to be in especially short supply for romcoms lately—though, as Drinking Buddies demonstrates, they haven't entirely disappeared.