When filmmaker Alex Holdridge decided to move from the cozy creative enclave of Austin, Texas, to Los Angeles, California, things were going well. He was going to make it. After all, he had premiered his first film, the ribald teenage comedy Wrong Numbers, at the 2001 edition of South by Southwest to sold-out crowds and studio interest. "I walked home, and on my answering machine, every studio had called," he remembers. Numbers also impressed screenwriter/director Jessica Bendinger (Bring It On, Stick It), who took the director under her wing, and they worked together on a Hollywood pitch for a potential remake. Things were falling into place. A career as a filmmaker was in the cards.

Sure, the young director had 150 dollars to his name, but he figured that he could just crash on a friend's couch until he got a job as a waiter. But disaster struck, and struck quickly for Holdridge; his car broke down, flipping over onto the side of the highway, his stuff strewn across the road. "My plans changed," he says, over the phone from California. "I saw a throwaway camera behind the grass, and I leaned down and pumped the shot [of the accident]." Once he had that souvenir of his failure, he recalls thinking, "I've got that photo, man, I need to find a story that uses that photo. There are some writerly tricks that you use when as you're working it out, and it ultimately has a payoff."

The ultimate payoff, and use of the photo would have to wait, however, as Holdridge was transitioning to LA. Things didn't improve in California: his longtime girlfriend broke up with him, his laptop was stolen, and despite studio interest in Numbers, he was hired to write it on spec (i.e., for no money). In the interim, he went back to Austin to work on a second film, Sexless, a romp about twentysomething relationships. Time passed, and when he returned to the Left Coast, Numbers-the-remake was essentially dead—word got out that another studio was preparing a similar movie following the adventures of two teenagers looking to buy a pack of beer. That film, of course, was last summer's giant hit Superbad: although, it must be noted that the filmmaker is entirely too polite to point fingers at a specific film or person.

This soul-crushing round of terrible luck led to his latest project, In Search of a Midnight Kiss, which premiered at the Tribeca Film Festival in 2007. With all that disappointment and frustration fueling his creative energies, when a friend called to say that he had just bought a new HDV Sony 2100 prosumer camera for $4,000, Holdridge decided to get his friends together to shoot something. The resulting Kiss starts on New Year's Eve, where Wilson (the excellent Scoot McNairy, who you may recognize from the current Washington Mutual "Kangaroo" ads), a screenwriter, is having a rough go of it. Some of his problems, a stolen laptop, a lost girlfriend, a car accident (complete with the photo from Holdridge's crash), may sound familiar; save the kicker, when Wilson's caught masturbating to a shoddily photoshopped naked picture of his roommate's girlfriend. At the behest of the bemused couple—post-masturbation embarrassment—Wilson puts an ad on craigslist looking for a holiday date. The abrasive actress Vivian (Sara Simmonds) answers, and the two start to connnect, ever-so-tentatively, walking around downtown Los Angeles, showing a different side of themselves and the city on film.

While Kiss has a loose, improvisational feel, Holdridge says, "It's far more scripted than anyone wants it to be. I wanted to do something about the heightened sense of loneliness on New Year's Eve. Online dating sites go through the roof right before then." Much of the script was shaped by a preproduction walk exploring forgotten parts of the city with Simmons. Of course, as the story pivots on a guy and a girl walking and talking together, the film clearly echoes the work of another director with Austin roots, Richard Linklater's Before Sunrise: "I'm a big fan of that movie. Rick and I are friends. It's a really solid movie. I wanted to do something in that vein, but with more bawdy humor, more sexual, and more plot."

Shooting in black and white for a "romantic, classic" feel, LA is one of the stars of the film. Holdridge finds the beauty in its buildings, imbuing the much-maligned city with character and history. "LA is an amazing place to shoot," he says. "It's so gorgeous and under exploited." According to Holdridge, Broadway is lined with amazing abandoned movie palaces that date back to the 1930s, and these days they're filled-in storefronts for electronics stores, only accessible through the stacks of DVD boxes by the back partition. Serendipity drove some of the shooting: "it got windy," he says, regarding a pivotal scene, "and it makes it epic, like a David Lean movie."

These scenes are cut to tracks from Austin bands Okkervil River and Shearwater, two of Holdridge's favorites. In his Austin days, the director struck up a friendship with Okkervil River frontman Will Sheff (who also played in Shearwater until 2006), and they'd nerd out together on movies and music, where Holdridge was introduced to some great films like McCabe and Mrs. Miller, and he happily recounts how one night where he and the musician hung out in the editing room, and then Sheff went home and wrote the lyrics to "My Good Deed," a Shearwater song that appears prominently in Kiss and its trailer. The director loves how the music is "emotional and evocative," and when the musician left some demos with him during an LA visit, he snuck a couple of "swatches and ideas of songs," "Lines" and "Mermaid" into the film. Of course, Sheff only heard the songs for the first time "at the Tribeca premiere, in front of an audience. It's really cool, because especially if you're a big Okkervil River fan, these songs are only in my movie."

Holdridge's artistic success with Kiss also had another effect—it reconnected the filmmaker with his family. His family didn't support his pursuit of art, but when the film's initial edit, which had about 1280 cuts (as much as a horror movie), melted down his PC, they banded together to get him a Mac so he could finish the film. Despite his momentum, however, Holdridge still lost a tooth during those dark days, and he didn't have the health care to fix it. In fact, he still doesn't have health care, but hopefully that will happen once his next project gets going. He has several options—an adaptation of Jonathan Ames' Wake Up, Sir!, a "romantic and noirish" film called Hate in Paris, "in the vein of The Third Man," amongst others. But after a bunch of small victories and false starts, it's the swooning Kiss that gives Holdridge the momentum to make a filmmaking career. And why shouldn't it be? After all, it's a classic story, says Holdridge, "We could've set it years ago, with vaudevillians walking around LA...the masturbation scene would've been the result of weeks of work over a stereoscope, but the effect would've been the same."

Alex Holdridge will be at the IFC Center screenings Fri-Sat at 8:05 and 10:10.