Never Sleep Alone: the sexy self-help cabaret (and book it inspired)

A Tampa native finds success in NYC with her one-woman show and book.

I’ve known NYC-by-way-of-Odessa multi-talent Roslyn Hart since we were awkward fourth graders, then more awkward teenagers. She was the straitlaced, outspoken geek to my unruly alternative freak, dramatic and outrageous where I was restrained, with a repertoire of songs, impersonations, theatrics and off-the-cuff humor that got her into trouble when it wasn’t entertaining everyone within hearing distance.

An overriding theme of our friendship was my sexual experience and her resolute lack of it due to her vow to remain a virgin until marriage. She didn’t, but she was still pretty chaste by the time she left Florida to make a name for herself in New York City. More than a decade later, after working her way up from singing waitress to writer and star of her own one-woman cabaret show, Roslyn has not only surpassed me but made a career of her expertise on socio-sexual situations via her onstage alter ego, Dr. Alex Schiller, “a hand-holding ass-kicking sexual fairy godmother.” The show, Never Sleep Alone, plays out like an interactive seminar on how to become the one everyone wants, with the audience broken up into two sections — the voyeurs, or onlookers, and the singles, active participants who must carry out any orders given by Dr. Alex, which means the possibility of getting pulled on stage for impromptu blind dates and demonstrations driven by the key principles of Dr. Alex’s self-help book.

Never Sleep Alone has held a residency at Joe’s Pub since 2011, sells out every six weeks or so, and has earned glowing write-ups by the New York Times and Huffington Post among others, likely spurring the publishing deal Roslyn landed in 2013. “When I first started the show, I pretended that I had a book. And then I got a deal for an actual book,” she explained. “And what started as satire became a really effective way to give advice. If I could sum up what it took 15 years for me to learn in 200 pages, and make people laugh and inspire them to take action, I’d succeeded.”

The result is funny and at times absurd, but underscored by undeniable truths, including the importance of maintaining an air of mystery, breaking tired social habits, caring about yourself and your appearance, and exuding an air of confidence and well-being. Despite the condom on the cover, it’s not a book about promiscuity, but really “about getting over your fears and learning how to live a sensual and inspiring existence, the life that you want to lead, whether anyone else is there or not.”

Check out highlights from our recent conversation below, pick up a copy of Never Sleep Alone here, and visit to get sensible dating advice, read testimonials or watch for updates on a national tour that could bring the show to town in 2016.


Let’s discuss for a moment how you went from virgin until marriage to bonafide expert on socio-sexual situations?
When I moved to the big city, I went from being someone in a very small conservative pond to this place where you could be anyone you wanted to be, you could reinvent yourself on a daily and nightly basis. Being a singing waitress and being an actress I had to do that in my professional life, and I just started to realize it’s fun to do in my personal life as well. Also, growing up kind of an “ugly duckling,” I was always the dorky, funny one. In New York, all of a sudden I’m meeting these people from all over the world, and they think that I’m the sexy one and the mysterious one and the intriguing one.

In a strange way, 9/11 is actually the reason I decided to move to New York. When those planes hit, I realized, ‘Holy fuck, life is short, if I don’t move to New York now and live my dream of becoming a performer and writer, and doing all these things I said I was going to do since I was a little girl, then it’s never going to happen.’ It also made me realize, you can’t wait for “the one.” You could die at any minute, so why would you deny yourself emotional pleasure and physical pleasure, because you’re waiting for this one perfect person?

When I got to New York, I realized there are millions of perfect people and different fairy tales we can have. “Happily ever after forever and ever” isn’t viable — it should be thought of as the exception, not the rule. As a society, we need to write a new fairy tale and tell people it’s OK to fall in love many times and that you can experience different kinds of love. That’s a stronger and healthier fairy tale. We’re doing ourselves and the next generation a terrible disservice by perpetuating this Disney myth, and telling that the more you love and make love, the less value it has. I think it’s the other way around — the more people you can have physical, emotional, romantic and sexual connections with, the better. It makes the world a better place.

I started to believe that 10 years ago, and that’s eventually what led me to want to do this show. I found that I was happier when I started realizing that, love can happen in a night, and it doesn’t mean it’s not love if you never see the person again. Love can be strong for 5 years, 10 years, 20 years, and then one day, you wake up next to that person and say, ‘You know what? There’s nothing here anymore.’ I’ve seen so many people who stay in unhappy situations for way too long because of the pressure that society puts on them, because you’re seen as failure if you’re actually honest with yourself and your feelings and you examine your situation and ask, ‘is there chemistry here, are we growing, are we still learning from each other... or has this run its course?’ So many people that are brilliant in their professional lives stay in bad personal situations, and they think it’s better for the kids. It’s not.

Describe the stage show to me as if I’d never seen it.
There are two sections in the audience: a singles section and a voyeur’s section. When you buy your ticket, you have to decide if you want to be in the singles section – which means, you become an active participant in the show, you get discounted tickets and get free champagne, but anything Dr. Alex tells you to do, you have to do it. You’re sitting at communal tables with complete strangers, you’re drinking and talking before show, and once the show starts, you might get pulled up on stage for blind dates, on stage demonstrations. I might tell you to kiss a complete stranger, because why the hell not? And everybody does it, and everybody loves it. If you are in a monogamous relationship or you are timid, you sit in the voyeur’s section, and you pay more money, and you watch the rest of us have a damn good time.

It’s almost like playing spin the bottle with hundreds of people, but better.

Tell me about how music plays into the show.
In the same way you go to a mega church, there are the traditional “hymns,” but we use pop songs like church hymns, and the music functions in the same way as it does in church. It’s hypnotic, it’s repetitive, it’s something everyone feels confident singing, and it evokes an emotion. Guilty pleasure, bring you together, scream it at the top of your lungs kind of songs.

So the first thing that happens is the entire audience sings a song. As you would in church. Singing together really helps the audience become more connected, mentally, physically, emotionally, and it really accelerates social interactions, and it accelerates everyone losing their inhibitions and having a good time. So many people spend hundreds of dollars and have to get so drunk before they can have a good time, and I wanted to create a night where I hastened that, where, in the first five minutes, you are talking to a stranger, in the first 10 minutes, you are kissing a stranger. And then, if you want to, you have 50 first dates in 50 minutes or less.

Dr. Alex is such an absolutist. Someone described it as sexual fascism meets sexual Buddhism. Because she’s so loving and so benevolent but she’s like, ‘Do what I say or get the fuck out. I don’t talk to sexless, scared, ugly people. That’s Dr. Phil’s job. I’m Dr. Alex. This is NSA. You’re making out with a stranger. And if you don’t like it, leave.’ And everyone goes along with it because there’s no fear of rejection – because someone else is making you do it. 

The show is essentially a seminar on how to become the one everyone wants, and we go over principles from my book. When I first started the show, I pretended that I had a book. And then I got a deal for an actual book. And what started as satire has, more and more, become a really effective way to give advice. It’s still funny, still somewhat absurd, but there’s undeniable truths in the book and in the show.

When I got the book deal, I realized it was an opportunity to teach people what it took me 15 years to learn. If I could sum up what it took 15 years for me to learn in 200 pages, and make people laugh and inspire them to take action, I’d succeeded. Most people just read self-help books and don’t actually apply them to their daily lives. I wanted to make my book very interactive, I wanted the readers to feel that Dr. Alex is always there for them. So people can write into me, I tell them when they complete an NSA challenge – because each chapter of the book ends with an NSA challenge that sends the reader out into the world – I say please send me the results of the challenges, and I write back to everyone. The great NSA stories, I publish on the website.

While it's dating advice taken to extreme levels, there are alot of underlying truths — maintain an air of mystery, always exude an air of confidence and self-content, break your tired social habits, etc.
There’s a condom on the cover, but it’s not about promiscuity – nowhere in that book does it say, ‘go out and fuck a bunch of strangers.’ It says, ‘if you do what I say, everyone is going to want to sleep with you, and when everyone wants to sleep with you, you have the power to get whatever you want.’ And nobody can deny that that’s true.

The book is really about getting over your fears and learning how to live a sensual and inspiring existence, the life that you want to lead, whether anyone else is there or not. And it is that contentment with yourself and with this beautiful new world you are creating that attracts people to you. Everyone wants to live like that, everybody wants to be the star of their own movie, but nobody knows how. So in the book, I give them step by step directions on how to become the one everyone wants and how to lead a sensual and adventurous life.

Did you always have a live band in mind for the show?
I did. The vision was always, that it should feel like a mega church. Growing up in Florida, the mega churches that I loved to go to were the ones that had a live band. One Christmas Eve, my mother dragged me to Grace Family Church on Van Dyke Road. And I remember thinking they were so brilliant because they had these Power Point projections, and they were tying the sermon into what was on the screen – they did a CSI about the birth of Baby Jesus, and they called it Christ Scene Investigation, and they had a live band and they projected song lyrics with the music. It really brought everyone together and it was most fun I ever had at church. That really influenced me, going to that service and a lot of that is reflected in my show. We project song lyrics, that way everyone knows the words. Dr. Alex says ‘Sing or get the fuck out,’ so everyone sings.

Tell me about the band – do you notice that musicians never sleep alone? Why is that?
That is very true and specifically in the case of my band. It’s amazing the power musicians have. There’s always something very powerful about a musician. If you’re up on stage, and you’re taking people to that magical place, where the spirit and the libido and the intellect all come together, they’ll worship you…. because you took them there.

The music is really important and live band is really important for that driving beat, too. Because there’s that pulse of music, it builds the momentum and it really compels people into doing some crazy awesome shit, stuff they wouldn’t normally do. It makes you feel protected, it’s like you’re sitting in a cradle of music.

What music really sets you off for the performance ahead?
Moby’s Last Night; it captures a New York night from start to finish. There’s a line I love, “If this be my last night on earth, let me remember this for all that it’s worth,” and that’s an overriding theme of the show: This could be your last night on earth — what are you going to do with it?

Scroll to read more Music News articles

Join Creative Loafing Tampa Bay Newsletters

Subscribe now to get the latest news delivered right to your inbox.