Singles in Los Angeles – Sienna Sinclair

Singles in Los Angeles: Sienna Sinclaire


The singular author of Naughty Girl’s Guide to Los Angeles wants to teach women how to enjoy the sexy side of the city and to discover their sexual power.

Singles in Los Angeles – Sienna Sinclair
Sienna Sinclaire, at home with her beloved miniature Yorkie, has a unique perspective to share with other singles in Los Angeles. Photo by Todd Young.

Sienna Sinclaire, a single 34-year-old entrepreneur with a college coed’s natural beauty, is just one of some two million singles in Los Angeles. She lives in a multistory condo just south of Brentwood and, despite being a single woman who lives alone, she selected a unit with street access, not like the others that lie behind the security gate.

It’s almost Halloween and her front yard is decorated with fake tombstones, a life-size witch, big plastic spiders and fake tombstones. She opens the front door wearing a striped sundress, smiling, petite; natural in every way, with just a few blond highlights in her sleek, straight hair. She seems a bit cautious, not sure what to expect from the journalist who’s come to interview her about her own particular style of living single and her recently published book, Naughty Girl’s Guide to Los Angeles.

Inside, her condo is stunning, the décor a bit like a boudoir. An enormous crystal chandelier hangs from the high ceiling. Above the fireplace is a six-foot-tall, sepia-toned vintage photograph of a nude woman. Three enormous matching mirrors lean against one wall, there’s a black candelabra on the mantel, a big, fluffy white rug lies in front of a white leather sofa and French doors lead out to a private garden.

Sienna shows me to a chair next to the lit gas fireplace. Her 10-year-old miniature Yorkie looks hopeful as she sets a three-tiered, English-style tea tray with tiny cream cheese sandwiches and baked sweets on the small table between us. Next she brings a Turkish tea pot, a deep coral with gold trim and matching teacups.

It’s clear from her home — its size, its location, the expensive furnishings, the luxurious details — that there’s money to be made when you know your way around the sex industry.

Naughty Girls Guide to Los Angeles
The first of a series of sexy
travel adventure books
by Sienna Sinclaire.

Q:  Your book is quite the work – lots of information, nice artwork and quality photographs. Was it difficult to do?

SS: It took two years. It’s not the hardest thing I’ve done — that would be my website: It’s massive and not finished yet. I’m still putting together all the articles for it.

Q: What inspired you to write the book?

SS: Well, I’d wanted to write a book and I’d blogged about my naughty travel adventures for a long time. I wanted something really nice — great photos, nice paper — women like pretty stuff. This book is definitely for women. It’s a great gift. The book has everything from sexy restaurants to things that are hard core. It’s up to you to define what turns you on, and what you want to do.

Q: You use that word “naughty” a lot. It harkens back to when you were a kid – like “you’re a naughty girl.”

SS: I’ve always been the person who wants to do something naughty because I thought it was fun. It’s not as in “bad.” It’s lighter, more playful. When I do my naughty lifestyle coaching, people say, “Is it all about sex?” but that’s not what it means at all. A naughty lifestyle is just being confident in your sexuality.

Q: The historical tidbits in your book are fascinating. Is history one of your interests?

SS: I’m a huge history buff. I knew Los Angeles had a naughty history but you don’t hear about it that much. I had to read a lot of different books to find out all the details.

Naughty Girls Guide to Los Angeles, history of lingerie
A peek inside of Sienna Sinclaire’s Naughty Girl’s Guide to Los Angeles.

Q: You’re very open about your sexuality. How did you become so liberated about sex?

SS: When I was younger, my mom would walk around the house naked and I was never modest about being nude as a kid and I’m still that girl today. As I got older, the guys I dated wanted to experiment with me and I was very open to it. And in my 20s, in college [University of Charleston, international business major/French minor] I never thought sex was bad because my parents never had that attitude.

Q: Is that your ultimate mission? To encourage people to express and enjoy their sexuality?

SS: Yes. To be more confident. When I go to Europe, women are a lot more confident. Women in Los Angeles try so hard to be pretty. They think to be “naughty” they have to get a boob job, bleach their hair blond, wear really short skirts — and yeah, guys still want to do you when you look like that, but when it comes down to it, they’re not really going to want to date you. I just got back from 5 weeks in Paris and I didn’t see one bleached blond girl. No fake boobs. No one was trying hard — it was more of a tease. Not over the top or in your face like you see here in Los Angeles, where we have all these plastic surgeons that make you feel like crap about yourself.

Sienna Sinclaire channels her inner vamp
Sienna Sinclaire channels
her inner vamp.

Q.: If someone asks what you do for a living, what do you say?

SS: It depends on the situation. If it’s a date, or friends, or just some people that I can tell are open, I say, “I’m in the sex industry.” Because that’s what it is. Sometimes when I’m traveling and meet people who might be more conservative I say, “I’m a writer, I write about sex and relationships.” I’m more discreet and I take it from there.

Q: Is that because you feel people will be making assumptions about you?

SS: It’s not assumptions. It’s like when you’re in a library, you know how to behave, you talk quietly. There are social norms and there are just some people I don’t care to get into it with. There are times I’ll say things and people will get really mad at me. And I’m not talking just about for what I do for a living — I mean because I don’t want to experience marriage or kids. People always ask “Why don’t you want kids, what’s wrong with you?” I’m like, “Why aren’t you a doctor, what’s wrong with you?” People can be so afraid of doing something outside of the norm, outside of the box.

Q. You’re very entrepreneurial — where does that drive come from?  You seem to have a never-ending variety of businesses and projects going on all at the same time — your websites, your books, your movies, your sex-toy store, your sex coaching.  

SS: It seems like a lot but it’s really all part of the same thing. I have an assistant who sets appointments and keeps my house in order. I have a photographer, a video guy and two PR people. I have staff that helps me but nobody updates my website except me.

Q: You say you’re in the sex industry, but this could mean a lot of things. It could be prostitution, it could be writing erotic literature — it covers a lot of possibilities. What does “sex industry” mean as far as you’re concerned?

SS: When I say “sex industry” a lot of people get upset. Like strippers, they will say they’re not in the sex industry, but they’re taking their clothes off, guys are getting hard and they’re probably rubbing a few off in the back. Or dominatrix women, they don’t want to say they’re in the sex industry, but they are. We all are.

Q: The sex industry seems to have so many paradoxes, one of the biggest being that it’s illegal to be paid to engage in a sexual act – but if there’s a camera in the room, then it’s legal because it’s a First Amendment right. Any thoughts on that?

SS: I think it’s funny and jokingly tell guys that if they want to hire a prostitute, to just put a camera in the room, fill out the 2257 paperwork, tell them it’s for your website or even for your own personal use, and then it’s legal.

Sexy isn’t always pornographic with Sienna Sinclaire
“Sexy” doesn’t have to mean pornographic as seen in this 1950s style
pin-up pose of Sienna Sinclaire.

Q: Do you ever run into any legal hassles?

SS: I have a lawyer who is in the adult entertainment industry and he’s one of the best. I pay a lot to be legal. It’s strange because the whole thing about the porn industry is they a have the law called 2257 and it’s to protect people who are 18 and under, and of course, we don’t want minors to get into porn either, but they put all these tiny little rules in to try to detour you from producing porn or having an adult website. The majority of the sites you see online, they’re not legal. If the authorities wanted to crack down, they could.

They can inspect you anytime. The laws are crazy. You won’t know that if you don’t have a good lawyer and still, my lawyer says if they want to, they’ll find something to get you on.

Q: There’s the idea that women in the sex industry are being exploited by a man somewhere, someone who makes them do it, or they are made to do it as part of an organized crime group. Is that true?

SS:  In my book, I write about how there are so many women who are in the business who run and own their companies. Jessica Drake and Jenna Jameson are just two women who exploit the porn industry — just like I do. You can make a lot of money in this industry if you do it right. And yes, there is sex slavery and it’s a big problem, but that is something entirely different.

And as for organized crime — we are making too much money without that. Why would we want to have that? I go to the industry events and the shows — these are big-time businesses that make millions of dollars. Why would they jeopardize that by getting involved with organized crime?

Q: Let’s talk about your commitment to live the single life. Why do you want to be single? Why does that appeal to you?

SS: When I was younger, in my early 20s, dating one guy at a time wasn’t working for me. I was always cheating on them. There was this one guy I cheated on … I felt bad … he wanted marriage. I was upset because I didn’t want to go through life hurting people. People tell you you’re supposed to only date one person at a time, but why? So I decided to come up with my own dating rules and I decided I would have open relationships and I would be honest. I would tell men upfront that I didn’t want to marry, that I didn’t need a piece of paper to be happy, and at 34 I still don’t have the desire to live with anyone.

Some guys think I’ll change. That happened with one guy, and six months later, when he saw that wasn’t the case, he broke up with me.

Sienna Sinclair
Sienna Sinclair

Q: How often do you like to see a boyfriend, when you have one?

SS: Well, since I’ve been honest about my rules, my relationships have lasted longer. I’ve been dating a guy for six years. I have no desire to live with him. I am so independent. I enjoy my alone time more than I enjoy my time with other people. I feel if I’m with people for too long it sucks energy out of me. But when I’m alone, I get all my energy back.

It’s taken him a while to realize that about me. At first he thought I wanted to be alone so I could date someone else, but he’s realized it’s because I really do want alone time.

Q: That need to have time alone seems to be a common denominator with a lot of singles in Los Angeles. Did you always feel this way?

SS: It took me a while to realize because I was trying to be like everyone else. But now, with my own rules, if guys can’t handle it, I know that they’re not for me.

I would like to have a relationship like Simone de Beauvoir’s relationship with Jean-Paul Sartre. They dated for 50 years, never lived together, never had kids and she was by his bedside when he died. They had other lovers and at times would even go traveling with each other’s lovers. To me that was a great relationship — the most romantic story I’d ever read.

Q: So marriage, traditional marriage, sounds like it would be death for you?

SS: I would probably just kill myself. It would be like being in prison. To have someone telling you what to do every day … if someone was around all the time, I’d get very claustrophobic. The only reason the guy I’ve been dating for six years has lasted so long is because he gives me my space. I don’t make those promises either like “Do you see us living together in a year?” or “Will you love me forever?” None of that. I say we’re together now, we’re having fun, let’s enjoy ourselves and not make things complicated by getting all weird and emotional. Let’s take it day by day without any expectations or time frames.

Q: How do women react to you? Do you have female friends?

SS: I have a few but I prefer to be on my own. Girls are needy. It’s like a relationship: “Why didn’t you call me?” If you are my girlfriend, you have to be fine with me not calling you or just randomly texting you to say hi. And be fine with us going out once a month.

Sienna Sinclair at home in West Los Angeles
Sienna Sinclaire relaxing at her home in West Los Angeles.
Photo by Todd Young.

Q: What about men?

SS: Men can be very intimidated by me. Performance wise, sometimes in the bedroom they can’t … one guy said he couldn’t get it up. I said let’s not focus on sex, let’s just relax. But he was so freaked out he just got up and left. He texted me later. He said, “I’m sorry, but when you took me to your bedroom I thought you would expect me to do all this crazy stuff and I got nervous.”

I’m like, “What are you talking about? Let’s just have sex!”

And no lazy lovers. If they get lazy, it’s time to talk. I don’t want to be the one who puts out all the effort. That doesn’t work. That’s one of the things about relationships. People get comfortable in them and don’t want to work anymore.

Q: Where do you meet guys?

SS: Online, or when I’m out and about. I like to go out to eat alone. I was at the Ivy a while back, eating alone, and had a famous gentleman hit on me. If I hadn’t been alone, it wouldn’t have happened. I don’t really like bars. I tell women I coach to get out, slow down, leave the smart phone in your purse, don’t’ read a book — just look confident and act like you’re enjoying yourself. And you have to dress up — you can’t go out in your sweats with your hair in a ponytail. Girls complain, “No one looks at me, no one talks to me…”  Well, what do you look like when you go out?

Q: We were surprised to see SingularCity in your book — it’s such a PG-rated website.

SS: You don’t have a dating site, but you can go there to meet people. And I’ve always like Singular. I subscribed to the print magazine. The people in the SingularCity social network seem nice — not cheesy like on dating sites. I went to one of’s Stir events and it was like a meat market. Everyone was constantly looking around to see who was coming in next to pounce on them. Is she better? Is he better? SingularCity seems more upscale and laid back. It seems like a good place to meet people.

Q: Do you have any new projects in the pipeline?

SS: The second Naughty Girl’s Guide — this one for Las Vegas. This book will be similar to the Los Angeles book but with a different girl on the front and a Vegas background. But of course, the movie industry is in L.A., so that won’t be part of it. It will be more about the entertainment industry. Vegas has a very naughty history by the way, with the brothels and all.

Q: Are you always thinking of ideas of what projects you’re going to do next?

SS: Oh yes, constantly. I read one book a week and I am constantly getting new ideas.

Q: What do you do to get away from work? Do you ever want to get away from things related to sex?

SS: This is my passion. People say, “Oh, you work so much.” But I don’t see it that way because it’s a hobby for me. I love what I do. It’s not like work. It’s a lifestyle. I don’t want to step away from it. I like it.

Copyright © Kim Calvert/2012 Singular Communications, LLC.

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16 thoughts on “Singles in Los Angeles: Sienna Sinclaire

  1. The brain is the biggest sex organ, introducing the full spectrum of senses in the act of love to include levity and humor is part of an holistic experience. My playful words relating to an article titled “Naughty Girl’s Guide to Los Angeles” was to summarize the author’s eloquent message cloaked in humor, a useful tool in a puritanical America. Opposition to my approach would be logical had this article been an academic research paper on sexual behavior, the response might in fact show how far we have to go as a society in being truly sexually liberated.

  2. Why is it (in this case Carl) that it’s a man that has to make an immature comment, Sienna I admire you, our American society has a long way to go when it comes to adult relationships, you’ve got your work cut out for you. Also it is great to see someone who is chic and posh talking about the oh so taboo subject of sex instead of someone of a more vacant nature! Bravo!

    1. Men will be men Elizabeth :) And you’re right Sass, he’s probably not joking! Thanks for the nice comments Elizabeth. Much appreciated :)

  3. Interesting that people get more upset when they find out she wants to stay single and doesn’t want kids then they do when they find out she’s in the sex industry!

  4. Well! I have to admit, when I started reading this article, I had all kinds of negative stereotypes in my head about people who work in the “sex industry” — but it seems to be working just fine for Sienna. I like her courage to follow her own path instead of following a more conventional lifestyle that would not honor her true self.

    1. Men will be men Elizabeth :) And you’re right Sass, he’s probably not joking! Thanks for the nice comments Elizabeth and Martene. Much appreciated :)

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