Alex Holdridge tells Nick Dawson how his love-hate relationship with Los Angeles led to an improbably tender tale about looking for a companion in In Search of a Midnight Kiss.

The moral of the story is that good films come to those who persevere. It took writer-director Alex Holdridge an arduous decade of work to get there, but with his third feature, In Search of a Midnight Kiss, he is finally achieving the success and recognition he deserves.

Holdridge‘s journey began in Austin, Tex., where he spent four years making his first film, Wrong Numbers (2001), a comedy about two teenagers on a night-long quest for alcohol. It won the Audience Award at the Austin Film Festival and had a two-week, sold-out run at the Alamo. He followed up with Sexless (2003), a smart Austin-set rom-com that won the audience and jury awards at SXSW. Holdridge decided to move to L.A. to take advantage of his momentum, but was dogged by bad luck: He crashed his car en-route to California, and once in L.A. his girlfriend left him, and the laptop containing the one copy of his new script was stolen. He was moving forward with a Hollywood remake of Wrong Numbers when he discovered that a film with an identical plot, Superbad, was already in the works.

Holdridge‘s pent-up frustration and catalogue of mishaps found expression in In Search of a Midnight Kiss, an all-or-nothing roll of the dice written in two weeks and made on a shoestring budget by Holdridge and a group of old friends from Texas. Set on New Year‘s Eve, it‘s the story of Holdridge‘s alter ego Wilson (Scoot McNairy), a downtrodden screenwriter, who looks online for a last-minute date so he can have someone to kiss as the New Year arrives. He meets up with Vivian (Sara Simmonds), the first girl to respond to his Craigslist posting, but the signs are not good: She chain smokes, slugs vodka from the bottle, is belligerent, callous and supremely manipulative, and treats men with utter disdain. Though romance seems impossible, the two somehow keep hanging out and, as they wander around the East Side of L.A., Vivian‘s layers of aggressive resistance begin to peel away.

Despite the inherent modernity of its characters and their situation, there is something classic about In Search of a Midnight Kiss. Holdridge has a great ear for dialogue, and the verbal jousting between Wilson and Vivian plays almost like a contemporary screwball romance. The characters walk around L.A. — a city where everybody drives — and Holdridge reimagines its old-fashioned downtown area as a miniature New York City, with d.p. Robert Murphy‘s sumptuous black-and-white cinematography recalling Gordon Willis‘s work on Manhattan. As Holdridge subtly transforms his characters from disillusioned cynics to cautious romantics, his resistance to the city he lives in slowly softens. Sweet, sexy and sophisticated, In Search of a Midnight Kiss has been a huge crowd-pleaser at festivals worldwide and it seems inconceivable that, when the film is released here this summer through IFC, U.S. audiences will not similarly fall in love with it.

From conversations we‘ve had before, Midnight Kiss seems to have been inspired by your life a few years back. Yeah, I moved from Austin, Tex., to Los Angeles. I‘d made a few films in Austin, which has this great indie film scene. The whole Richard Linklater world inspired a whole lot of people who are very film savvy. I never went to film school or anything like that. I just wrote a script and watched a lot of movies. I wasn‘t a rich kid [who was told], “Here‘s a trust fund, go for it.” I was just kind of like, “Fuck it, we‘ll save up and figure it out.” I was working three jobs and piecing [Wrong Numbers] together in my tiny apartment, which is a really great way to learn. And so after [my next movie], Sexless, premiered, it won a bunch of awards, and then I was like, “Alright, I‘d better go to L.A. and try to remake that project [Wrong Numbers] I was working on.” And that‘s when my life kind of got like Midnight Kiss. Everything just fell apart.

What went wrong? I was in this really fun creative environment with all these great collaborators and the next thing you know, I‘m standing in the desert and my car‘s upside down with every single thing I‘ve got scattered across the freeway. I had thought if I had $150 and I got to L.A. and could get some kind of job waiting tables, I‘d be okay. And I drove and crashed my car [laughs] and ended up like, “Okay, fuck, now everything‘s out of whack.” All of a sudden I‘m in L.A., which is very spread out. There is no sense of a film community — it‘s very sink or swim. My girlfriend and I broke up and she moves to Japan, just like in Sexless. All of a sudden I‘m there in this new city in this really crappy apartment in Hollywood, the same one from Midnight Kiss, and I couldn‘t get a job. There are so many good-looking actors who are out of work and are waiting tables — you‘ve got to go in and fight for a waiting-tables job! It‘s not like Austin where you can have a working-class job, write for the Weekly, save up and write your scripts. The expenses are too high, and the wages are lower. I was offered two jobs for $7 an hour. Who the fuck can survive on $7 an hour? So then I was like, “Fuck it, we‘re going to finish this script and it‘ll be fine.” And then my laptop was stolen, just like in Midnight Kiss.

So the scene in the movie is completely autobiographical? Someone biked by and took it exactly like it happened in the movie. [laughs] I was talking to my sister with my nephew, and it was stolen from the same stroller like it was in the movie. It was like that moment where everything you have that makes you you is gone: your girlfriend‘s gone, your car is gone, you‘re in a whole new city and you‘re in this weird apartment. You have your one friend in the other room, but other than that you‘re lonely as fuck. I‘d go downtown and walk around in this postapocalyptic world and be like, “What the fuck is wrong with this city? How can all these beautiful theaters be left [abandoned]?” I built up so much hatred for this city. I felt like it had no heart. The downtown is destroyed; we‘ve allowed our heart to go but the body still functions. Just seeing all that, it really was the one time in my life I very seriously considered suicide.

What pulled you back from the brink? My parents. After all that time, I went to go visit them and they could just sense like, “Wow, you‘ve died.” They bought me a camera, I was able to get some work and then I ended up doing creative projects. Had I not had the camera, I don‘t think I could have survived. It‘s so funny because my parents and I had such a falling out about me becoming a filmmaker. They were kind of like, “You‘re on your own.” And in a way, them helping me was kind of like the beginning of the détente, I guess. And then my [cinematographer] friend Robert Murphy called: “I just got a camera, you want to shoot something?” And that was it. That‘s how we made Midnight Kiss. Two weeks later, I had written the whole script for Midnight Kiss, he arrived and we started shooting. We didn‘t ask anybody, we weren‘t waiting for money, we didn‘t have any money, I just called everyone I worked with previously and said, “We‘re shooting a movie.” Everyone literally dropped whatever they were doing. [We had a crew of three] and the actors helped move the lights. I said, “I think I have $2,000 before I‘m maxed out, let‘s use that.” And that‘s how it began.

So the budget was $2,000? Well, originally. Ultimately we spent about $12,000 for the first round of DVDs to submit to festivals. Of the $2,000, I had $1,000 in cash and then [actor] Scoot [McNairy] was like, “Alright, let me help,” and so we split everything. We were so fucking hungry to make a movie again, and I felt like it had been so long for someone to give us permission or the money to do this. I was so pissed about L.A. and this whole experience that I thought this was going to be my “I hate L.A.” movie. I was originally going to call it If L.A. Fell Into the Ocean, I Wouldn‘t Miss It. [laughs]

At what point did your animosity toward the city turn into affection? The film‘s ultimately a very romantic picture of your side of L.A. Here‘s the thing about that love-hate relationship: All these filmmakers that I love, even ones like Rick Linklater, they had their time in L.A. You kind of have to come out and pay your dues. There is this bit of romanticism where you‘re like, “Well, I don‘t know if it‘s going to work out, but we‘re going for it.” So it‘s hard for me not to romanticize, especially when you walk downtown. Sara [Simmonds] and I had walked around downtown together, and we had found all these amazing locations — most of them that are in the movie — just by strolling around together and having these really fun conversations. There‘s this sort of lost, sad past about L.A., and there‘s almost no respect for this history because it‘s just wallpapered over. You see these fucking awesome theaters that are just turned into shitty electronic stores and there are cheap electric banners plastered over something like the Globe Theater. How the fuck does this even happen in the world? It was like anthrax had gone off in 1919, and the buildings are still there but the people are gone. I certainly wasn‘t intending it to be the love letter that it ended up being, but then when I watched it I was like, “Wow, I guess I have a lot more affection for this city than I thought” [laughs]. Like the affection for what Hollywood represents rather than what the city is like exactly. I guess those two kind of collide.

When we spoke at a film festival, I remember we discussed the similarities with Swingers. Swingers was shot in the exact same area, and was obviously a big influence. It‘s a very common story in L.A. — arriving and kind of making your own peace with the city and surviving here. But having watched Swingers and having lived in that exact area, it was like, “Man, that world just does not fucking exist. People don‘t go like, ‘Hey baby, let‘s go to the swing clubs.‘ There‘s no such thing!” I mean, that was a moment in time, and that movie has so much heart and love in it — it‘s about the camaraderie of these friends. I wanted to do something like that but I wanted it to be like how it is in my world, because I don‘t see that world. I wanted to capture the way this is now. So that was kind of an impetus there.

Tell me about the black-and-white photography, because that‘s a really big part of the film‘s distinctiveness. I think so many people just fall in love with the look of the film because it‘s beautifully shot. I wanted it to be old-fashioned. I was like, “Fuck the way indie movies are made. I don‘t care.” And though I like a lot of those movies I did not want to give it the faux documentary look. We just set these parameters right off the bat, like we were shooting this old-school — over the shoulder, longest lenses we can possibly do, locking it down, we‘re going to be on the sticks, we‘ll do the tracking shots once we‘re out. We‘re moving but like a Billy Wilder movie or a John Ford movie rather than anything modern. I just wanted to make it like an old-fashioned movie mixed with the sensibilities of a modern story. It‘s very contemporary, and I wanted it to be completely of our generation. We‘re MySpaceing and texting and that‘s just the life of being in L.A., but I didn‘t want it to be so “Oh, that‘s so 2007” or whatever. I wanted it to be more transcendent of time a little bit. So the idea was to mix the sensibilities, because of course the humor is incredibly bawdy. So if you kind of take bawdy, foul-mouthed, sexual humor and you give it this romantic and classy veneer in terms of shooting, that just felt right to me. And so that‘s how we began.

To what extent was this film make or break for you? Oh man, had this movie just played at festivals, I don‘t think I would have ever... I mean, it‘s sold all over. I‘ve been to Istanbul and Greece, and all these places, and it‘s hard to imagine that it‘s something that I was shooting with my friends in this tiny little world and cutting it in my 350 square foot apartment that has computer equipment, cameras and a futon. That was my fucking life. I was editing this thing for 10 months. I was in my own tiny little bubble. My brother and sister saw the beginnings of the cut and they were like, “Do not go back to wait tables, this is working.” To have my sister and brother give me a few thousand dollars to not have to get a job to finish editing, and then my parents do the same thing — which was a big deal because they had never done that at that point — it was kind of this reconciliation of my whole family, and they‘re all in it, which is kind of fun, too.

I have to ask you about a credit on IMDb which says that you directed the 30th Annual Mrs. America Pageant. [laughs] That‘s like a comedically hilarious phase of my life. That was one of those things that got me out of the hole. Of course it‘s real humiliating that someone else would put that up on IMDb, [laughs] but, yeah, it was a job I took. It was hilarious for me because I had made the movie Sexless, which is all about a guy who was completely obsessed with having sex with people, and all of a sudden I‘m standing in a pond in Palm Springs, brokenhearted, horny and alone, shooting these gorgeous married women with this camera with a wide-angle lens, running up their bodies while they‘re pouring water on them [laughs]. Yeah, it was an absolutely hilariously stupid thing I did to make, I don‘t know, $6,000 or $7,000 — that was an enormous sum to me at the time. Of course now I wish I could pay IMDb $7,000 to have it removed.