Author Interviews

Fortunately, Ueland’s past inhibitions have no effect on his writing. “Accidental Playboy” is a wonderfully unguarded, almost sweet book, especially at its tawdriest moments (often also its most awkward). Playboy die-hards, those who send the Fearless Reporter boozy late-night e-mails, tell Ueland that he’s the luckiest man alive. But what we see — between the forays to strip clubs — is a tortured, self-professed nice guy fumbling across the country in the company of many women, his conscience and ultimately his own happiness.

Ueland spoke to Salon from an airport in Chicago.

You were working on what you call The Bestseller, your novel, when you went on the Playboy bus. At what point on the trip did you realize that you had a new book, a very different one, on your hands?

One night when I went out in Portland with a woman named Eve and her boyfriend. At the end she said something like, “Someday you should write about women who can’t leave men who aren’t good to them.” It’s funny, that’s when it really started to feel like I was in a book, and so from there on I thought: “As long as this keeps up like this, it’s a book.”

Did you get the impression that a lot of these women felt like Eve — that they were looking for an escape?

Absolutely. If you’re in New York or L.A., you get used to being around people who “got out,” and it seems like it isn’t hard to do that. But there are a lot of people back in the rest of the country who are looking for something more than their current life but feel trapped for whatever reasons. So this bus coming through town … frequently, it was like, “Take me away.”

Wait, let’s back up and start with you. What were you like before this trip? Did you even read Playboy? Did you frequent strip clubs, ever date strippers?

You know, I was purely a prostitute guy.

Of course you were.

No, not at all. Even when I was describing being in a strip club in the book — I really was not familiar with that before the trip. Growing up, like every adolescent, I had my visual connection with Playboy or Vogue or the lingerie section in the Sears catalogue. That’s a rite of passage. But no, it’s not like I even had a subscription to Playboy. I’m not a porn person. I’d never met a stripper before.

And bikini contests were new to you too, apparently — though, as you noted, judging them is a surprisingly uncomplicated task.

Yeah. Right. I mean, I went to a theater school when I was a kid. My favorite sport is ladies’ figure skating.

Really?

Well, I do have normal guy things.

And you also had all of these strong feminist relatives. What did your family think of the whole thing?

It really goes way back to my great-grandmother and my great-aunt. My great-grandmother, at least in Minnesota, was really in the vanguard of [feminism]. These two great-aunts of mine said that, given the times we live in, Playboy 50 years later is almost a quaint, kitschy thing. I don’t think it was their first choice for what they wanted me to do. Forceful, amazing women around is something that I grew up with. It takes you a while to realize that not every guy has that same outlook.

You seemed like you were more the type to be protective of women and wary of men who might ogle them. Is that true? Did you really feel like a dirty old man when you first set out on the trip?

I did. About the whole question of taking advantage of people … just taking their pictures and putting them on the Web site. These women are just blindly signing these releases. I was definitely like, “What are you doing? What are you thinking?” So as I went along, I either became corrupted or I thought: “Far be it for me. They are getting something out of this.”

I imagined that before you went on the trip you sat around with your friends, had a few beers, and speculated about how many women you would sleep with. Or at least all the hot women you would meet. Is that right?

Absolutely. Guys are going to elbow you and say, “Oh, dude …”

But did you personally expect to?

I was so not dating at the time, so I was the only one who knew how comic it was that I was going to be on the Playboy Miss Millennium bus. I probably did have this fantasy version of what it was going to be — all these glossy Playmates coming to the bus. But the reality was that it was not that clichéd. It was secretaries taking off on their lunch hour and coming by the bus.

At one point did you notice that you were starting to feel more comfortable with the whole thing and looking at the women differently?

The first time I’m in the back of the bus, these three young women strip off their clothes and are basically jumping around. That’s when I’m really uncomfortable. And then when I bring a woman, Daisy, out into the center of the bus — that’s the first time I enjoyed taking a photo. I wasn’t feeling like “I’m a complete pervert” and I just enjoyed taking the woman’s photo and was trying to get a better photo.

Eventually you get so comfortable with it that you knew how to tell them to pose, how to distort and contort their bodies, all that.

It was like that photographer’s banter that’s so perfectly parodied in “Austin Powers.” There were times that we really felt we were trapped in that world. You end up saying these cheesy things.

Like what?

There’s a scene when an extremely sexy woman, Kandi, comes on the bus and later my boss tells me that I actually said something, kind of unknowingly, like “That’s great!” Or “Hot!”

“Yeah, baby”?

“Way to go!” I don’t know. But my threshold for embarrassment is unbelievably low. I’m still mortified that I was even in that situation and was egging the whole thing on.

But it sounds like Kandi had that effect on everyone. I mean, what was the deal with Kandi?

There are certain people that give off an animal vibe. Who knows what it is. With her it was women and men. And it was so unintentional, she was so not trying to. It just made everybody unsettled and she was like, “La di da di da.”

You mentioned feeling cheesy before and it seemed as if Sophia — the publicity person for Playboy who also rode on the bus — was always monitoring your cheesiness. Did you have to give in to cheesiness if you wanted to be a part of the spirit of the whole thing?

At a certain point, I just had to go with it. But Sophia was always there to mock me. She was a great sidekick. She really applauded my transformation and was a fan of mine. She was reassuring me that I wasn’t as bad as I thought I was and that I should go with it. But she was definitely getting her digs in along the way.

I actually thought that you would end up getting involved with her.

Yeah, if there’s a movie that will probably be what happens.

It did seem likely in a movie-ish way: I spent six months with Playboy Miss Millennium candidates, but much to my surprise, fell for the behind-the-scenes, bookish girl.

She’s just a great modern woman.

What about Vegas, the real dirty old man of the bus? He’s the only fictional character in the book.

There were some legal landmines that I had to get past. Some problems with Playboy and some other fears from Warner Books. There are other male characters in the book, who I don’t talk about, and then Vegas, the fictional character.

But I also wondered whether you created him as your alter ego, or maybe the dirtier side of you, or the dirtier, raunchier guy that you wanted to be.

I was obsessed with the idea of a Vegas, this sort of anti-doppelgänger. I felt like I came of age in the ’80s, when pornography was so under attack and it was all about boundaries and political correctness. As kind of a sensitive guy who had a feminist background, I felt like I took that all way too far. And here was a guy who just was oblivious. Or was he oblivious?

So the scene in the strip club, during one of the bikini contests when you and Vegas cheered them on — where the girl was pouring oil on herself — that scene is true?

Yes, it was the most down-and-out bikini contest. I mean, I’d never seen a bikini contest, but this one really was so tawdry.

What were they doing that was so weird to you?

The Playboy bus is like the multimillion-dollar upscale version of titillation, so it was beautiful to see the squalor, the lowest end. I mean, it wasn’t like there were bad things happening. But it was this really stripped-down bar; this contest was going on for dirty cash in the cash register.

Yes, $72, right? You were really into that contest. It seemed like one of the first times you were really enjoying yourself.

I felt like this one woman was this performance artist or something. It was so hard to figure out why she had the full-on dark jeans and a dark shirt and was pouring oil on herself. At a bikini contest. All I could figure was that she knew what she was doing and was mocking the whole thing.

You couldn’t see through her top?

No, I mean, she was just making her clothes heavy.

You had all these interior monologues throughout the book — you’re thinking about these women and wondering where they’re from and what they’re about. And then at one point you stop and say, “Maybe I’m just thinking she has a really great ass.” Was there some point where you turned that voice off?

For me, that really was some kind of mini-epiphany — there is a cheesy factor that you can’t escape, something about men and women coming together and sexuality and all that. It’s animal and a little embarrassing. It’s that thing — when you say things in the bedroom it’s OK, but if someone outside heard them you’d be mortified.

How did you control yourself? Lots of times you were in these small spaces with naked women, taking pictures of them. And they flirted with you.

That really was an issue. I started off that trip so disconnected from my own libido … and I’m not saying that to make the story work. That really is true. I’m an example of extreme self-consciousness. But you can only be so self-conscious and be sexual. As I kind of let go a little bit … there is a scene where I’m taking a woman’s photograph and … I don’t even know what to say …

You finally became aroused.

Yeah, absolutely. That was a pivotal moment. I’m thinking: “This is so low, so kind of trashy, and what is going on here?” On the other hand, well, what else are you going to feel? She’s naked, we were creating the sexiest image possible.

Right, because before you were worried why you weren’t getting turned on. In the very beginning.

And I really do think it was because I was excessively self-conscious and excessively worried about not wanting to offend somebody.

What did the woman think? Did she notice that you got turned on?

That’s the thing. I think, absolutely. Yeah. Um, I mean, hopefully.

Got it.

Right. It was in the spirit of the moment. Usually, photo shoots are lighting people and makeup people, and there’s financial pressure involved. But this was intimate.

You were in a lot of weird locations.

It really came to a crisis point when I was at a birthday party in a hotel room [and detailing what was happening for the Web site]. Being so aroused with a woman there was a really bizarre situation. And they were taking photographs and it’s all posing but … that was the point where my brain started short-circuiting over the whole thing. You’re there and you’re like, “Well, we’re naked, we’re against each other.” Your brain is saying, “This is sex.” And then, “This is work.” And I didn’t know how much further I could push messing with my mind.

You did have a breakdown moment in Detroit too, where you just started hysterically laughing on the street.

That’s true, too. The day after posing this woman and taking her picture — the absurdity of it hit me and what had become of me. I just started laughing so hard, and crying. Then you become aware of the fact that you look like a crazy person.

Did any of these women get upset with you? In the end, did you offend anyone?

There’s a scene that got cut out because it came too late in the story. I end up in my hotel room. I wanted to take someone … you know, I had a hotel room that had really great light —

Suuuuure.

Yeah, I know. But there was this very sweet, attractive 18-year-old candidate, and I said, “Do you want to come up to my room and take photographs and do you want to bring someone along?” I was thinking she might bring Sophia, but she said, “No. That’s fine. Let me just tell my mom.”

Oh no.

So I said, “Why don’t you bring your mom?” OK. So this woman was naked under sheets. I was posing the sheets around her. I have to say, those were my best pictures. And her mother was saying, “Isn’t she a beautiful baby?” And I’m thinking, “How far will this mother — who seemed like a good, level-headed mother — go?” I felt like I was the one who would be putting the brakes on.

For the most part though, in the book, it seemed like a happy time for all. At one point you’re in your room with some woman and you write, “Who knew it could be so fun to throw macadamia nuts all over the room?” Whee! I pictured the whole thing in slow motion. Was it really that fantasy-like and silly and joyful? Or was that the alcohol?

Definitely, it was one of those boozy late nights where everything becomes funny. And egged on by alcohol. We were full-on rollicking. I’m sometimes still amazed how all that stuff played out. It felt fictional.

I guess in a way all these women are living out their “dreams.” And you worked for the dreammaker. But you must have seen a lot of sad cases too. It couldn’t have always been positive.

Of course, and that’s what I allude to … In the book, the people that I’m picking out to deal with are the most fun and quirky and interesting. The other side was depressing … so many young women who are already divorced or already married and have a kid or two at 20, 21. The ones I talked to tended to have a sense of humor. But the ones who thought they were going to a job interview, that was always a little sad.

Well, you said that about Eve. You were interested in her and then you were disappointed when she said her biggest thrill would be to be in Playboy. What did you expect?

She just seemed … very bright and funny. I’d been thinking that maybe she’d want to do it for the money but it really wouldn’t mean anything to her. When she did say that, I was kind of surprised. I never could totally understand.

I thought it was interesting when you met one local stripper and she drove this really nice car and had a nice house and cooked for friends all the time and was taking French lessons and planned to move to France. She made a lot of money and was living this great, full life much like the one you’d want to lead.

I know, she had this really idyllic life. At times, you catch yourself looking down on this lifestyle and then you realize, “Well, her life sure sounds better than mine.”

Yeah, it occurred to me too. So, you slept with how many?

Two. There was a lot more making out, though.

And then — this is another story that got cut out — there was this woman who had been on the German pairs figure-skating team in the Olympics —

Oh, wow, your perfect woman!

I know. I have that skating thing. She had a serious boyfriend. But she really felt like we hit it off. I met her boyfriend at a party later and he said, “Oh my God, you really got to my girlfriend.” She was somebody who I thought could be long-term.

But it was this pleasant thing of the trip: I felt my sexuality was restored and I was able to walk away from that and not feel bad. And she did have this boyfriend and he seemed like a good guy.

How has this changed you in terms of the type of women you’re attracted to? Has it? Are you more open now? It’s five years later, of course.

After this, I ended up writing for Nerve and Playboy about the sex industry. I ended up with a soft spot for people in the sex industry. They are outcasts, and they’re very nonjudgmental because everybody judges them. I’m probably more open-minded, but I haven’t dated any strippers or anything.

But do you find yourself sizing women up with the mind of the Playboy photographer?

Certainly when I was on that bus. It’s a slippery slope once you start looking at people like that. Nobody is perfect. I think people are really beautiful in general. And I still love taking people’s pictures and I love people’s faces.

Once and for all it confirmed to me that there are so many things, as a guy, that you’re supposed to feel a certain way about. One of the big ones is that if there are a lot of women around, you’re supposed to sleep with a lot of women. I really realized on that trip how much I don’t enjoy sex unless I do connect with somebody. It feels like that’s an embarrassing admission because I’m a guy. You know what I mean?

Of course. I’m sure some people, especially women, would think that makes sense, some might think that it’s sweet, and some would think it’s bullshit. But this trip drove that home for you?

Yeah. My therapist was like, “Oh, you’re screwed.”

At the same time you do credit this experience for loosening you up, helping you to enjoy all things sexual a bit more.

I do. I am so Scandinavian, Midwestern. It’s an uptight background. It’s such a perverse idea that I had: that if you desire somebody, it’s something to hide. That there’s something to be ashamed of about desire. I’m definitely a lot better about that and it’s a healthy change.

So you weren’t “permanently damaged” at all, were you? You did worry about that at one point.

It is an interesting question: Is there a point of no return? It’s like people who join religious cultlike sects. It did make me think about the idea of changing your core person and whether that’s possible. Toward the end of the trip I was just letting myself go. In D.C., toward the end, I started to get creeped.

You still feel you’re a “nice guy,” whatever that means.

Yeah. Somebody I know was talking to Christie Hefner and saying about me, “He’s the kind of guy you’d want your daughter to date!” I’m a painfully nice guy. Nice guy to a fault.

Well, you’re no Hugh Hefner anyway. You gave it a go, but …

He has the Midwestern thing too. And I think he had a fairly serious religious background. I did feel that connection — that I was having a small version of his experience.

What’s he like?

I was just around him at those parties at the mansion. On one hand, I do applaud the guy for creating his own world. He does live by creating the world he wants and realizing he doesn’t need to go along with the sheep. That said, I’m utterly amazed that this is still amusing to him, that it’s still satisfying 50 years later.

When I see him at the party and it’s like, “Oh, we’re doing the bunny dance again,” it’s just a small example of his entire life. He would be an interesting guy to talk to, and he must be a very bright guy, but it seems like he’s jettisoned that for the life of frolicking.

Many do. You saw a lot of celebrities at the mansion. What was that like? We actually had an interview with Bill Maher up yesterday and he mentioned his affection for the mansion … and he was one of the celebrities you saw there, right? What was he doing again, something with tequila?

Body shots. The parties are like a 13-year-old boy’s fantasy: The ratio’s in favor of the guys, the women are all really pretty. And in this case there are celebrities. But it’s a lot of C-level celebrities. You know, Weird Al Yankovic is always there.

And Bob Saget, right?

Yeah, and Scott Baio. They’re the 2000 version of the guys who used to hang out in the ’70s — you know, like Jimmy Caan and those guys … now James Caan’s son hangs out there a lot.

And so, in the end, were you happy with Miss Millennium?

They picked these twins … Playboy is always a little behind the curve of what’s hip. Apparently, there was a day when they were in the forefront. Now, they’re embarrassing. Their effort to leap on the Latin American explosion came a couple years after Ricky Martin. Getting the twins for 2000 — it was so hokey. Those were women we never saw on the bus. It felt like Playboy just went to a modeling agency and got them from there. But I don’t know.

I like the idea that we looked for the Playmate of the Millennium and didn’t find her. You know — she’s not out there! Time to shut it down!