I'm obsessed with pickup artists. I admit this freely. My obsession may or may not have reached fetish proportions; I can't tell anymore. This has been going on for years, but eventually I plan to write an article called "Confessions of a Pickup Artist Chaser: Long Interviews With Hideous Men." I am not lying. (If you're willing to publish it, call me.)

At this point, most people have heard about the pickup artist subculture. The 2005 best-seller The Game, penned by rock scribe Neil Strauss, chronicled his meteoric rise from a shy, lonely guy who could barely speak to women, to one of the world's most famous pickup artists. In the process, he pulled back the curtain on a community that until then had been largely underground.

That community is a group of guys trading advice on how to pick up women, often selling tutorials on how to do so or beating their chests in classic (sometimes assholish) masculinity displays. On one end of the personality spectrum are super-shy guys, as Strauss paints his former self: men whose extreme social anxiety leads them to seek advice for basic stuff, like having a conversation with an unfamiliar girl. On the other end of the spectrum are terrifying misogynists who I wouldn't want to meet in a dark alley—or, well, ever. There's not always a clean or obvious division.

My feeling is that there's good advice in the community for genuinely kind shy guys. But sometimes, it's so mixed with misogyny and cold-heartedness that wading through it can feel like panning for gold in a sewer. (And because some ethical guys are so desperate for advice that they'll wade through that, I've often thought that it could be good for feminists of all genders to try to develop our own pickup curriculum. Since there aren't yet any actively feminist pickup curricula, I've tried making a list of the least misogynist.)

Compared to many feminists, my stance on this community is positive. But honestly, I sympathize with feminist anti-pickup rage—sometimes I, too, pull back from my relatively positive stance. One such moment came at the beginning of this year, when famous pickup guru Gunwitch (who was briefly mentioned in The Game) actually shot a woman in the face. This occasioned much feminist discussion (a post I wrote on a feminist blog drew 322 comments), and some feminists drew parallels to the alarming 2009 murderer George Sodini, who was a passionate adherent to many pickup ideas as well.

After the Gunwitch shooting, I had to take some time off and remind myself that, in fact, I've talked to many pickup artists who specifically work not to be misogynist. There are even occasional pickup artists who actively seek to engage feminism; I don't always agree with them, but I give them points for seeking an ethical and gender-liberationist conversation about these dating tactics. Neil Strauss himself included a number of feminist quotations in The Game. (Which isn't to say that The Game gets a free pass from feminist analysis. Some of the tactics in it make my skin crawl.)

Strauss recently released a new book, Everyone Loves You When You're Dead. (Here's a great graphic review by Ward Sutton.) To write it, he went through his two decades of celebrity interviews to find moments of intimacy and truth. The thought of talking to such an accomplished interviewer was intimidating, but when the legendary pickup artist came through Chicago on promotional tour, I just had to request an interview.

Girls get social anxiety too. I was so nervous on my way there, I almost turned the wrong way down a one-way street and had to perform an incredibly dangerous u-turn in a busy intersection. By the time I made it to the Book Cellar, where Strauss was answering questions and signing books, the place was like a mosh pit. It was so full that I couldn't get in the door. I had to stand gazing through a crack as Neil Strauss, wearing an awesome sparkly purple tie and an engaging smile, chatted with his fans. The vast majority were male; almost all the questions were not about his latest book, but about The Game.

Notwithstanding the overt discussion of game, Strauss totally charmed me. He seems unconscious of his fame; he comes across as humble, kind, and genuinely curious about other people. He has friendly personal conversations with his fans, and freely admits it when he doesn't know what he's talking about. When we finally sat down to chat, he was totally chill about the fact that most of my questions weren't even about his latest book.

Clarisse Thorn: It seems like authenticity preoccupies you. I've heard your new book Everyone Loves You When You're Dead is essentially a meditation on authenticity, is that right?

Neil Strauss: The new book is like...I wanted to understand these people, who they are, where they come from, what made them, what drives them. Authenticity is the starting point, and then you start digging from that. First you have to wipe away the mask and the bullshit and the deceit and the self-deceit, and then you get to start. In the book, for example, if you look at my Howard Stern interview for Rolling Stone, the first thing is you don't want his radio persona; you make sure he's giving you the persona his friends and his wife know. What I'm trying to find out changes depending on where I am in my life. The interviews, to me, were as much about them as to answer questions for myself. So now I'm interested in intimacy, so I'm exploring intimacy in my interviews more. Even though it's really supposed to be about them, I'll ask whatever I'm naturally curious about. It's kind of a covert autobiography.

CT: I've personally been interested in how authenticity comes up in The Game. It seems like a theme in the background; it's not overt.

NS: We also call it congruence: when who you are on the outside matches who you are on the inside. I think one of the many misconceptions about The Game is somehow that guys are being taught to be fake—I know I'm more real and more honest than I ever was before The Game, when I was too shy to really express myself. People go through a process of not being themselves. It's part of the journey. Through anything you have to struggle and get dirty in the mud and get to the other side and become yourself, and that's part of the process.

CT: This reminds me of pickup artist discussions around "inner game," where pickup artists try to develop personally by exploring themselves and their values and their life goals. I'm fascinated by the concept of inner game, because it's giving someone an opportunity to develop themselves, but it's doing it through the lens of pickup.

NS: What helps one's inner game, too, is just having some success: Success breeds confidence, which helps your inner game. To me there were two routes for The Game. One of them is that it becomes a funny blip on the pop-culture map where guys are wearing funny hats and coats and doing magic tricks. Or it becomes the beginning of a men's self-help movement—because self-help isn't emasculating anymore if you're doing it to get laid. After getting into pickup, all of a sudden a lot of guys become more spiritual and do things they would never otherwise do. It's kind of ironic—I was just remembering the other day that before I did The Game, I made fun of a men's New Age group in a Beck video I was in. Then, a few years later, I'm kind of at the center of a men's support group.

CT: Yeah, speaking of emasculation...the reason I got into looking at pickup stuff was that I was thinking about masculinity, and the issues that men have with trying to be masculine and match up to those standards.

NS: My next-to-last book Emergency is about masculinity as well—the other side of masculinity. Being able to build a house and build a fire, protect yourself. One side is to be successful with women, and the other is to be a man and take care of things.

CT: I heard that recently you've been thinking of training women to be good with men. Can I ask how you might advise a woman to have good game? What kind of advice would you give her for picking up men, and what kind of relationship advice would you give?

NS: My main thing would be a deeper goal, which is to realize how many choices a woman might make based on low self-esteem. I think that there is some degree to which you can help women be more successful with guys. The real simple thing is that guys are attracted by sexual possibility; that doesn't mean you have to have sex with them, but guys are initially attracted by the possibility of sex. So you can be a really beautiful person, but if you're really uptight you'll be less attractive. But the bigger choice is looking at what makes a woman sleep with a guy, looking at who she chooses to do that with, and seeing how much is based on a real connection with someone she wants to sleep with, and how much is based on self-esteem, whether it's being competitive with other women or—there are certain women hung up on guys, and they're only hung up on him because he didn't call. She fooled around with him a little bit, and he didn't call afterwards or was rude afterwards, and she wants that self-esteem back, so she's hung up on this guy. Another thing that kills me about some women is that you should judge someone by their actions, not their words. I'll be like "Look, he did this," and she'll be like "But he said this."

CT: Don't you feel like guys do that too?

NS: Not as much as women. I'm not an expert, but as far as relationships go, I do know this: In general, let a guy be a guy. A lot of women, not all of them, a lot of them feel insecure about men being men. Men get nervous about showing sexual interest, his full sexual side, because men's sexuality is seen as threatening. Also, a lot of women start trying to control a guy's freedom. I think you should give somebody their freedom anyway, but also, if you do that then you can find our by their behavior whether they're good for you or not.

CT: I noticed that you included a lot of feminist quotations in The Game, like Gloria Steinem and Jenny Holzer. Could you talk more about that?

NS: I felt like the main problem with the book, as I was putting it together, was that it needed more female characters. I couldn't invent another female character because there weren't any women giving advice in the community. So I thought, why don't I put in a female voice through these quotes? Your intention for a book is never the same as the reception. You know the Simone de Beauvoir book The Second Sex? I wanted to do the equivalent for male sexuality. On some levels male sexuality is everywhere in society, but on the other hand it's completely repressed: Men are afraid to show it because it will make them socially unacceptable as well as less sexually desirable. I wanted to write something that was honest about male sexuality, not like Maxim magazine or the billboards. The Second Sex is obviously a different book and much more philosophical than The Game, but my goal really was to do something like that.

CT: So how do you feel about feminism?

NS: I'm definitely not an expert, but it's splintered into so many things that I can barely define feminism. There can be people who are feminist, and people who hold the completely opposite view but are still feminists. It seems to me from the outside that there's a lot of people busy fighting each other rather than working toward their goals. It's a shame. Maybe you can tell me what feminism is.

CT: I think feminism is focused on providing positive choices and encouraging respect for women, but it's different things to different people. I'm on the sex-positive end of the spectrum, with a lot of focus on sexual freedom.

NS: Right, so there's sex-positive and then there's Catherine MacKinnon. Is Jenna Jameson a feminist? Is Catherine MacKinnon a feminist? I don't know.

CT: A lot of pickup artists talk about how much they hate feminism.

NS: Here's the deal. Anyone who hates something feels threatened by it. A guy who says he hates feminism (a) doesn't understand or know feminism, and (b) is scared of powerful women. Most attacks come from fear.

CT: You heard about the Gunwitch shooting earlier this year, right? How did you feel about that?

NS: I felt just devastated for the girl and her family. It was horrible. He was an unstable individual. If you look in The Game, he's only mentioned as an extreme element—I mean, his philosophy was "make the ho say no." I'm surprised it took this long for someone in the community to do something that stupid, but I would never have guessed it would be something that violent.

CT: A lot of feminists came down on the community especially after Gunwitch shot that woman.

NS: That's like when a politician does something bad and people say all politicians are bad. I think a lot of people say stuff about The Game who have never read The Game. Some people feel threatened by it. But when women have problems with the movement, I do understand. We still are a patriarchal society, as you know—men are dominant, and when the dominant group bands together, that's a threatening thing. So, to me, I can see that element of why it's threatening. I understand, but I also think people should explore why they feel threatened and why they feel angry. All my books have been based on my fears. The Game was based on my fears of social and sexual rejection, and Emergency was based on my fears of what's going on in the world. Everyone Loves You When You're Dead is based on the idea that people are threatened by other people, so they shit talk people they see as competition.

CT: If you were to critique any one thing about the community, what would it be?

NS: My big critique is that while once the community was a free flow of ideas, and—I'm partly to blame for this, with The Game and everything—now it's been commercialized. If I got into the community now I wouldn't know what to do. It's splintered into these niche markets—a guy gets in, he's like, "What do I do? I only have so much money to spend." You have all these guys saying there's only one kind of game, and it kills me, because the game is all those things. I think that show The Pick-Up Artist was good, but a long-term effect was to confuse the game with the surface elements. Wearing the feather boa and the fuzzy hat and the magic tricks isn't the game. But, that said, the game is about standing out from the average generic guy, and being unique and more interesting, but in a non-needy, non-desperate-for-attention way. The surface elements can change, but the deep principles are the same. It's about the social rules by which people operate.

CT: How do you feel you've developed during your journey from The Game to here?

NS: Bob Dylan said, "I'm never arriving, I'm always becoming." At these signings, people ask me what's it like to be perfect, and I'm like, "I'm not perfect!" I always tell them I'm not. I'm just a guy, I'm still on the path. I do feel like the insecurities I had about women have been cured and solved; it was like a two-year college for my social skills. I feel like I'm in a comfortable place; I've had adventures beyond what I thought was possible. But I know I have other challenges ahead of me. My own little thing is, I've always tried to be honest, with no fear. With The Game, I thought about doing it under another name, because I was so scared of the reception. But I think it really worked because it was honest. I try to continue to do that.