Although conventional wisdom says otherwise, men really do want to watch romantic comedies. Unfortunately, they're not the same ones that women want to watch: for every two dozen movies like The Proposal or the upcoming The Ugly Truth, there's maybe one or two like High Fidelity or Almost Famous. This week, men can add 500 Days of Summer to their shortlist of testosterone-driven rom-coms, thanks to its story of a neurotic twentysomething named Tom (Joseph Gordon-Levitt) who falls deeply – and increasingly desperately – in love with a comely young lady named Summer (Zooey Deschanel).

Cinematical recently spoke to 500 Days director Marc Webb via telephone about his experience making the film, which he admits contains more than a few chestnuts of wisdom he wishes he had at Tom's age. In addition to discussing the demands of juggling relationships both off and on screen, Webb spoke about the significance of releasing his Summer film during the hottest months of the year, and offered a few insights about the seldom-discussed but decidedly-substantive legacy of romantic comedies made and marketed to – and for - men.

Cinematical: When you started working on 500 Days of Summer, what was this movie really about for you, or what did you want to explore the most?

Webb: During the process it evolved a little bit, but to me it's a coming of age story masked as a romantic comedy. To me it's about growing up; Summer isn't just a girl, she's a phase of your life. It is something that we've all gone through and all experienced, and there's certainly a romantic element, and there's an examination of the ambiguity of certain kinds of relationships. But at the end of the day, it's how you negotiate that and how you deal with that that's important to me.

Cinematical: There are generational benchmarks of this sort for people of all different ages. For example, some of my younger colleagues really loved the film, while I enjoyed it but some of it reminded me of older, vaguely similar films. For you, was there any conscious decision-making in terms of figuring out how to distinguish 500 Days from other existing coming-of-age, romantically themed films like this one?

Webb: There was probably some of that in the writing, but I didn't write it, you know? But to me, my job was to be as loyal to the story as I could be. I think the story came from the writers' experience, and it wasn't a premeditated construct; it came from a real place, and that was I think why it sort of has its soul. So it wasn't really a reaction to any kind of movie, so much; in retrospect certainly we occasionally used set pieces from the romantic comedy genre, but those were things that are there because – there was a wedding scene because it evokes a sort of permanence, to a certain degree. There's reasons that we do it that aren't just based on a formula. But as far as setting it apart from other things, there wasn't really a conscious effort to do that; if anything, we tried to do the opposite. For example, it's not about Twitter or social messaging or eBay, it's about a very relatable part of your life when you're starting to get a more contextual view of what it is to love another person. So if anything we tried to remove it from a time period.

Cinematical: That said, one of the things that stands out about the film is its wealth of music and references to the 1980s. Was there a particular reason for you or for the writers that you chose that decade as opposed to, say, the '90s, which would more likely be the time in which these characters came of age culturally?

Webb: Well, a lot of the music that's referred to is from the 1980s. I'm 34, the writers are 30 and 29, and this is the stuff that they grew up on so it has a sort of shorthand cache. So The Smiths is a very specific kind of music that signifies something about the people who listen to it. But beyond that, as a narrative tool, if two people like The Smiths, you can see how they would think they have something in common, so that point is understandable and relatable to a lot of people so I think that was important. But there was a nostalgic twist to some of that music, certainly Hall & Oates was that way, but we used more modern music, like the Regina Spector stuff or the Wolf Brothers stuff, more of today. And then we went into Simon and Garfunkel territory, so it was really less about copping an era, and more about finding a tone and a lyric that was informative of the scene we were shooting, whether it was explicit with The Smiths, or it was implicit as in the case with Simon and Garfunkel.

Cinematical: There's a terrific scene in the film where a character says, "just because someone likes the same thing that another person likes, it doesn't mean that they're your soul mate." For you, what is it that you think these two people really share or what connects them that either the audience will recognize, or at least Joseph Gordon-Levitt's character responds so strongly to?

Webb: Well, I think that they're both young, they're both single, they're in this work environment where they spend a lot of time with each other, and when you mix that together and they're both attractive people, what else is going to happen? Romance grows from that, from proximity, and he may construe these things as destiny or fate or whatever, but the truth is, I suppose, that it's not uncommon for people to have similar interests, and how much you weigh that is really up to you. My feeling is that Tom reads too much into it.

Cinematical: Without giving away any of the plot, one of the things that seemed very authentic was the idea that a person you care about can want something with someone else that they say they don't want with you. How careful did you have to be to provide a sense of catharsis without vilifying the characters too much?

Webb: I think it's funny because people relate to the movie in different ways. A lot of people walk out of it really not liking Summer, and I feel that happens because these are trends – and I don't have the scientific evidence to back it up – that people in our parents' generation or grandparents' generation in particular are very resentful of Summer. They're like, "well, he's a good boy! Why don't you like him?" But people like us who have been on the frontier of singledom in our 20s, and I don't know what your experience is, but they are much more sympathetic towards her. But young people, like teenagers who haven't necessarily gone through heartbreak or don't know what it is to be on the other side of that can also be really resentful of her. But there's sort of a gap in there when people have been in the thick of that experience and know what it is to be ambivalent about a relationship and sure of it.

I wanted the audience to be in Tom's shoes, right? That was my primary objective, and I wanted people to be in love with her, I wanted them to be annoyed with her, but at the end of the movie I wanted us to have come to terms with her and at the very least understand her and want good things for her ultimately. It's very convenient to vilify someone like that, but I think when you stop being angry, that's when you get over a person, and it's not always easy (laughs).

Cinematical: How if at all meaningful is releasing this film during the summer? Do you feel like it plays to expectations of broad entertainment, or subverts them?

Webb: Well, it's tricky because our movie is called 500 Days of Summer, so we couldn't release it at any other time, or at least that's the prevailing wisdom. I actually think there's a pretty good crop of movies this summer; I think Up in my opinion is the best movie I've seen recently. I think that because people have been sort of consumed by some big action movies, they're willing to look a little deeper. But it's hard to say; I do think it's a pop movie and I think of something that's really acceptable but I think we use that pop in a way that's less obvious than other movies do. Our movie's funny, it's acceptable – I mean, hopefully, I don't want to be presumptuous – but it fits into that world a little bit. It's not that sort of winter, being-in-for-the-cold-months kind of movie. It's there, it's fun, when you walk out of it hopefully you feel a little bit better about things, or a little warm, and you have that hope in you when you walk out of the theater. Releasing it in the second half of the summer, I think people are looking for a little bit more depth, probably, because they've been sort of cashed-out by the bigger event movies.

Cinematical: Whether there's a movie like 500 Days you specifically remember, do you have a consummate summer movie experience that either obsessed or inspired you?

Webb: Boy, when I was a kid I loved Cannonball Run. I was so into that movie. But you know what I remember when I was a real little kid? My parents took me to a drive-in with Sword and the Sorcerer, and I was like so amazed. I might get chastised for this, but really liked Armageddon. I know it's weird to say, but it's true; I was a sucker for that movie. And when I was in college I went to study in Italy once and I watched A Room With a View, but I watched it on video. It's not the typical summer movie, but I loved it, and it has this summery feel to it, and I watched it in the summer, I remember specifically. It allowed me to kind of fantasize about Italy, and that was a fun experience.

Cinematical: This movie is the consummate romantic-comedy, coming-of-age story for men. Movies like The Ugly Truth and The Proposal validate the feeling that romantic comedies are primarily for women, but men have their version in films like High Fidelity, Rushmore, Almost Famous, as far back as Annie Hall. Why do you think it is that we seem to need movies like this to provide perspective on our romantic lives?

Webb: There's probably only so many movies about romance that can be sold to that audience, and it's a tricky thing because so often these movies have to do with female wish fulfillment. It's empowering as a genre for women typically, but it doesn't necessarily vocalize true emotions for guys; at the center of a lot of romantic comedies there's a genuine desire to contemplate relationships, but for me it doesn't resonate. But I think you hit on a really important thing, which is the coming of age aspect, and romance and relationships are a big part of how you learn to be a man nowadays, like how you identify yourself. Tom's arc in this movie is a really simple, very basic one; our film is a very small, very cordoned-off section of a young man's life. At the beginning of the movie, he is afraid to ask a girl out; there's that scene outside the karaoke bar, and she's like, "do you like me?" "Well, yeah I like you." And they have this sort of awkward thing and it's like there's a subtext in that scene which is that she's like "kiss me," or "ask me out," or "be a man."

He's off-kilter and he doesn't know exactly how to handle himself in that situation because he thinks, well, the universe will take care of this. I don't have to put my ass out there. I'll just hold my cards close to my vest and I won't have to be assertive. At the end of the movie, he asks a girl out, and that's his arc. It's a very small arc, but being afraid to ask a girl out at the beginning of the movie and at the end of the movie, he asks her out. And I think that we need to be reminded of how to be men occasionally when it comes to romance and relationships, and when it's told from the woman's point of view, very often it's not a very realistic portrayal of manhood. You need that guy's point of view to harbor that, but for some reason Hollywood doesn't think that men want to see movies about relationships because the formula, especially lately, has been geared towards women.

Cinematical: Do you think that this movie or movies like it provide an actual sense of perspective or catharsis about your own relationships, or those of your audience? Or do you think their purpose is better served by viewing them as pure entertainment?

Webb: Personally, when I read the script there's a line in the movie when Paul is talking to the camera and he says, "she's not the girl of my dreams. The girl of my dreams would have bigger boobs, like sports more, be a little hotter. But she's better than the girl of my dreams: she's real." That little thought, that little tidbit I think is really powerful. I read that and it articulated a feeling that I had that I hadn't been able to express in a really efficient way, and I think it's a reminder again of this sort of notion or this idea of romance can get subverted and perverted and it starts to lose its meaning. That statement unlocked that for me a little bit. Like I think that people are entertained because they are engaged, and they're engaged because you're talking about big ideas. I don't think they're mutually exclusive.