Cruel Valentine


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About Cruel Valentine

Known as “Chicago’s Own Community Chest”, Cruel Valentine is an award-winning, international burlesque entertainer, adult film performer, Dominatrix, actor, dancer, writer, and artist, Valentine began performing the art of burlesque in 2007. Since then, they have spent the past several years performing their way across the nation and abroad, racking up multiple awards and honors. Valentine is an independent performer, producer, and teacher of burlesque, as well as an adult performer with The Lust Garden, featured on Pink Label. is your go-to for all things Valentine, including a line of professional-grade pasties, vintage pin-up couture, and other titillating burlesque accessories. In addition to touring and teaching privately, Valentine has worked as a board member with several Chicago performance art organizations, as well as offering business consulting services to alternative, creative, and adult companies. Their teaching credits include various educational and speaking engagements both domestically and abroad, including workshops at the collegiate level at several of Chicago’s major universities, covering a wide range of topics including dance instruction, higher education, business, sexual health, sex worker rights, and more. With extensive experience in theatre, music, and dance, Cruel Valentine is a triple threat and then some, fusing multiple styles in their performances. A dedicated storyteller, they are never afraid to go there, or to make a mess with their art.

For booking, press, or other inquiries, please contact or fill out this handy contact form!

Learn from Cruel Valentine

Private Lessons and Creative Business Consulting Services

Cruel Valentine offers private and group virtual burlesque lessons! The curriculum is tailored exactly to fit students’ needs, abilities and goals. Whether you’re looking for a fun and basic burlesque themed workout, a novice seeking a boot camp to prepare you for your burlesque debut, or a seasoned performer seeking strength and flexibility training or choreography consultation, Valentine can create a custom class to suit you! Rates begin at $60/hour for individuals. Learn more and book here.

Additionally, Cruel Valentine offers their creative business expertise and career development experience in the form of one-on-one consultations with artists and small business owners looking to cement and grow their brand’s reach, success, and sustainability. In addition to assisting with everything from getting your business name registered, to sorting out self-employment and sales tax, Valentine also lends their recruitment and HR knowledge to those seeking work as well as those hiring for jobs, by full cycle recruitment assistance for small and niche businesses, and offering resume overhauls and mock interview services to those in the job market. Learn more and book here.


Who are you?

Hi! I’m Cruel Valentine! I am an award-winning, international burlesque performer, producer, educator, model, curator and artist. Feel free to explore my site to learn more about my career and accomplishments, and to check out my blog, photos, video, and a list of my upcoming appearances! Also, be sure to take a look around my shop, where I have all sorts of pasties, accessories, art pieces, photo prints, and other wonderful merchandise for sale. Should you have any questions, or if you’d like to reach me regarding a custom order or booking inquiry, please contact me here, and I’ll get back to you as soon as possible! If you have a question about my shop or its contents specifically, make sure to check out my Shop FAQ!

When will you be performing next?

You can find my full calendar of upcoming events, including performances, vending, workshops, and more, here! I tour regularly, so chances are I’ll be coming to a town near you at some point!

How do I book you for an event?

If you would like to book me for a show, workshop, photoshoot, art modeling gig, or private event, please get in touch! If you are a fan who would like to see me in your local shows, have your favorite producers reach out to me!

Will you perform at my event, teach me burlesque, or make me things for free?

I sure won’t! My unique skillset is the product of over a decade of hard work, a college education in musical theatre performance, ongoing maintenance and innovation to my repertoire, and years and years of experience, not to mention literally millions of rhinestones. I also have living expenses just like anyone else. My work is my livelihood, and while I enjoy what I do, I don’t do it just for fun. Exposure is not a currency that my landlord accepts, so neither do I.

I want to start doing burlesque! Where do I begin?

A great place to start is by taking classes! Training is so important, whether you’re a budding performer or a seasoned professional! I currently offer private lessons, and occasional workshops both in Chicago, and while on tour. I specialize in creating fun and challenging workshops for groups, as well as custom tailoring private lessons to my students’ needs, abilities, goals, and desires. In addition to in-person lessons, I also offer virtual act consultation. Contact me for information on how to get started!

Where else can I follow your work?

Lots of places! Please explore my modeling work on Zivity, GodsGirls, and Diverxity! Also, be sure to connect with me on Facebook, Twitter, Instagram, Tumblr, and Crushee!

Shop FAQs

Who’s in charge here, anyway?

Hi! I’m Cruel Valentine! I am an award-winning, international burlesque performer, producer, educator, model, curator and artist. Welcome to my shop! I specialize in pasties and other burlesque accessories, as well as art, photo prints and more! Please take a look around, and get in touch if you have any questions or a custom order request. For more information on my career and accomplishments, as well as photos, videos, and other fun stuff, please check out the main section of my site here!

What are your shipping policies and delivery times?

Please keep in mind that most items in this shop are made to order, so you’ll need to consider both construction and shipping time when making a purchase. Please allow at least 7 business days for item construction. I use USPS for most shipments. First Class shipping within the United States starts at $7, with an expected shipping time of 3 to 4 business days. First Class international shipping begins at $12 USD, and shipments can take anywhere from 2 to 8 weeks, depending on your country’s customs process.

What is your return/exchange policy?

Due to the intimate nature of these products, and the fact that most items are made to order, I am unable to accept returns. Please consider your buying choices thoroughly before checking out. I’m always available to answer any questions you may have before putting your order through! In the unlikely case that your merchandise is damaged or otherwise defective upon arrival, a refund or replacement will be considered. In order for your merchandise to be considered for return, you must contact me within 7 days of the item’s delivery. Any approved returns must be postmarked within 7 days of approval.

Okay, so about these pasties, what size should I get?

That is totally up to you, my friend! My sizing chart is based on the diameter of the pasties. Many people feel most comfortable with a pair of pasties whose diameter matches up the diameter of their areolas, or a little larger. Some find they like to go a little (or a lot!) smaller or larger than their areola. If you’re not sure, for your first pair, I recommend going with a size close to your areola measurement. You can always extend your collection later to include multiple sizes and styles. Additionally, I offer custom sizing in any size you can imagine. There is no “too big” or “too small”. You are perfect exactly as you are. Just send me the diameter of your areola, and I’ll be happy to tailor a gorgeous pair of pasties to your specifications.

How do these things stay on, anyway?

So glad you asked! You can purchase my signature pastie tape here! It’s my preferred adhesive for my performance life, and has gotten me through nearly 9 years of professional performance, touring, and modeling. This tape adheres more strongly as your body heat warms it, so it’s perfect for even the most active and hot-blooded of wearers. Just tear or cut off a few strips, press them around the back edges of each pastie, then remove the paper backing and press the pasties firmly to the breast area. Be sure to hold them in place for a few moments with your hands, or simply by putting on a bra, to ensure maximum hold. This tape is also a great quick fix for securing low-cut tops into place, or even to temporarily mend damaged hems and seams. Many factors can affect what adhesive will work best for any given person. Different skin types tend to favor different types of adhesives, and personal preference is a huge factor, as well. Always make sure that your breast area is clean, dry, and free of any lotions or moisturizers before you attempt to put on pasties. Some other preferred methods for adhesion include spirit gum, medical adhesive, carpet tape, and wig tape. I encourage you to experiment to find out which method works best for you!

Okay, then how do they come off when the fun is over?

My signature pastie tape stays on when you want it to, but is easily removable. Pull up the edge of the pastie and slowly, steadily peel away from the skin. For a little extra support, you may want to press down on the breast right next to the area you’re peeling back from. Some people have more sensitive breasts than others, and many factors can increase breast and nipple tenderness, such as PMS, HRT, pregnancy, nursing, piercings, etc. If your nipples are feeling sensitive, don’t worry! Sliding a moistened cotton swab underneath the edge of your pasties and gently swabbing as you remove them can help ease the process even more. Nursing balms, cocoa butter, and other nutrient rich moisturizers are great for treating sensitive areas after you take your pasties off, too!

How do I care for my pasties?

Pasties and accessories found on this site are spot clean only unless otherwise noted. These pasties are very durable and they will take care of you if you take care of them! Remove any residual pastie tape gently after use. You shouldn’t need to clean your pasties, but if something gets on them, simply wipe them down with a lightly dampened cloth. Keep in mind that certain varieties of prop liquids like fake blood may cause permanent staining on lighter rhinestones. Be sure to store your pasties somewhere safe and dry between uses.

Can I wear pasties anywhere?

If you plan on wearing pasties, thongs, g-strings, or other revealing garments for performance or any public occasion, make sure to familiarize yourself with local nudity laws first!

I want a pair of pasties that look like magical unicorns jumping over potted daisies and giving the middle finger. What section of your shop can I find that in?

My shop is mainly focused on providing a wide array of beautiful, durable essentials, however, I just LOVE flexing my creative muscles on custom orders. Get in touch here, and we’ll work together on making your ideas to come to life! In the past, I’ve tackled custom requests from the simple: hearts, stars, other fun shapes, all the way to wild and wacky undertakings like microwave pasties with operational doors. I also offer custom sizing on existing products beyond my standard sizing chart. All you have to do is ask!

What’s the deal with tassels?

My pasties can be made with swivel mounts, which all you to wear your pasties with or without tassels, and to switch different tassels (and other small baubles) in and out. My mounts allow for a full, easy 360 degree twirl. I offer a wide variety of beaded and chainette tassels here. Some specialty tassels and other clip on adornments will be made available seasonally, and can be made upon custom request.

Can I wear your tassels without buying pasties?

Probably not. If you happen to have nipple rings with small gauge jewelry, you can clip these tassels onto them, though extended wear is not recommended. If you do not have jewelry to attach your tassels to, then no. The clips on these tassels are not designed to act in place of a piercing, or to be hooked onto the nipple itself.

Vulva Art, you say? What does that mean, and is it hygienic?

Yes, it’s exactly what it sounds like! I create acrylic paintings on canvas, using my vulva. All of my paintings are sprayed thoroughly with a durable, glossy clear coat for hygiene, and to extend the life of the art itself.

The lingerie you have in your shop isn’t available in my size! What gives?

The lingerie in my shop is all vintage stock that I find on my travels and bring home to improve upon by hand-dyeing, rhinestoning, adding trim, etc. Since these pieces are vintage, sizes and styles are a game of chance. I work hard to stock a wide variety of sizes, but what I find is what I find, so I can’t guarantee that your size will always be available. I accept custom orders, though, and that includes upcycling and embellishment projects! If you provide a piece, I can upgrade it for you. Just get in touch!

I love your stuff! Can you provide me with the vendors you use for your supplies, as well as detailed information on your construction methods so I can make similar items at home for free, for my own personal use, or possibly even to start my own business?

Sure can’t! My suppliers and techniques are the result of years and years of hard work, research, experimentation, trial and error. To simply hand them over to stranger would be not only detrimental to my business and livelihood, but it would also be a disservice to you and your creative process. Success is much sweeter when you work hard for it. I encourage other crafters and artists to explore and work hard toward their own unique styles. Why do me when you can do you? Get out there and make something wonderful if that’s what you want to do!

I own a shop or run a show, and we would like to sell your items. Is that possible?

Absolutely! I will happily consider all wholesale requests. Contact me for more information!

Awards & Acknowledgments

Cruel Valentine Resume Highlights

Master of Arts Management, Expected May 2021
Columbia College Chicago
Bachelor of Arts, Musical Theatre2018
Columbia College Chicago

Academic Appointments:
Graduate Teaching Assistant, 2019 to Present
Columbia College Chicago
Feminist in Residence Fellowship, First Runner Up, 2020
Women’s Center, Northwestern University

Headlining and Featured Burlesque and Cabaret Appearances, 2007 to Present:
Madrid, Spain
Toronto, ON
Atlanta, GA
Los Angeles, CA
Ann Arbor, MI
Detroit, MI
Cleveland, OH
Milwaukee, WI
Minneapolis, MN
Delafield, WI
San Francisco, CA
Washington, DC
Ypsilanti, MI
Frederick, MD

Indianapolis, IN
Bloomington, IN
Des Moines, IA
Nashville, TN
Iowa City, IA
St. Louis, MO
Syracuse, NY
Columbus, OH
Saint Paul, MN
Austin, TX
Denver, CO
Pittsburgh, PA
Philadelphia, PA
Sonora, CA
Long Beach, CA

Awards & Acknowledgments
2015 Winner of the Burlesque Bitch People’s Choice Award
2014 Burlypicks Chicago Regionals Master of Tassels
2014 Burlesque Bitch Audience Choice Top 7
2014 Burlypicks International Finalist
2014 Unbustled at Unbridled Finalist
2014 Unbustled at Unbridled 2nd Place Audience Choice, 2nd Place Overall
2013 Burlypicks International Finalist
2013 Burlypicks Finals Best Improv
2012 Texas Burlesque Festival Audience Choice Award
2012 Gorilla Tango $500 Burlesque Thing Finalist

Performance Highlights
Thotless, Open Television, Season 1, Recurring, Self (Principal Role) 2019 to Present
Easy, Netflix, Season 2, Episode 7, Performance Artist #2 (Principal Role) 2017
Fire Ball Masquerade, Madison, Wisconsin 2013 to 2018
Fierce Queer Burlesque Festival, various U.S. cities 2013 to 2016
Show-Me Burlesque Festival, St. Louis, Missouri 2016
Windy City Burlesque Festival, Chicago, Illinois 2012 to 2015
Michigan Burlesque Festival, Detroit, Michigan Headliner 2013, 2014
ElectroBlues Cabaret, Madrid, Spain 2013
The Dirty Show, International Erotic Art Exhibition, Detroit, Michigan 2009 to 2011, 2013
Texas Burlesque Festival, Austin, Texas 2011 to 2013
Mondo Homo Queer Arts Festival, Atlanta, Georgia 2010

Professional Memberships and Activities
SAG-AFTRA Eligibility Est. 2017
Burlesque & Performance Community of Chicago
Industry Group Administrator, 2013 to Present

Educational Activities
The Leather Archives & Museum, Chicago, IL
Contributor, Guest Speaker on Sex Work & COVID-19, 2020
2020 Pandemic Sex Work Archival Interview Collection
Northwestern University, Evanston, Illinois
Center for Awareness Response & Education
Sexual Health & Assault Peer Educators
Guest Speaker on Sexuality, Sex Work, and Sexual Health, 2020

Northwestern University, Evanston, Illinois
Consultant for “Sexual Pleasure 201” Presentation, 2020

Sexual Health & Assault Peer Educators
SEA Conference, Columbia College Chicago, Illinois
Panelist on Graduate School for Self-Employed Artists, 2020
Northwestern University, Evanston, Illinois
Teaching Artist, Choreography Consultant, B. Burlesque, 2017 to 2019
Queer, Ill & Okay, Chicago, Illinois
Teaching Artist, 2016 to 2017
Women of the Now, Chicago, Illinois
Panelist on Sex and Sexuality, Poerotica, 2017
Victory Gardens, Chicago, Illinois
Panelist on Plaçage and Sex Work, The Body Politic, 2016
DePaul University, Chicago, Illinois
Performance Art Workshop Educator, Queer, Ill & Okay, 2015
Northwestern University, Evanston, Illinois
Performance Art Workshop Educator, Queer, Ill & Okay, 2014

Fierce Queer Burlesque Festival, Madison, Wisconsin
Panelist on Minorities in Burlesque, 2014
Harrington College of Design, Chicago, Illinois
Performance Art Workshop Educator, 2013

     Valentine, C. (2019). A Timeline of Fumbles: Presidential Response to the HIV/AIDS Crisis. A lecture presented at Columbia College Chicago as a part of Professor Alton Miller’s 50 Years of Civil Rights in Chicago course. December, 2019.
     LaRoux, S. and Valentine, C. (2017). Merchandise & Marketing: Mastering Your Side Hustle. A workshop on entrepreneurship, marketing, and income diversification for independent artists, presented at Free Range Office in Chicago, IL as well as virtually. August, 2019.
     Valentine, C. (2017). Patronage for the Modern Creative. A workshop on crowdfunding and patronage strategies for artists and creative business owners, presented at Free Range Office in Chicago, IL, as well as virtually. August, 2019.

Editorial and Production Board Appointments
The Virtual Strip Club, Chicago, Illinois
Founding Committee Member, 2020 to Present
Jeezy’s Juke Joint: A Black Burly-Q Revue, Chicago, Illinois
Executive Production Board Member, 2011 to Present
Queer, Ill & Okay, Chicago, Illinois
Programming Committee and Curatorial Panel Member, 2016 to 2018
Zivity, LLC, San Francisco, California
Editorial Board Member & Social Media Team Advisor, 2014 to 2018
No-Tell Cabaret, Chicago, Illinois
Co-Producer, 2014 to 2016
Festival of Flesh Variety & Burlesque, Chicago, Illinois
Assistant Producer, 2014 to 2016
Queens of Cups Productions, Ann Arbor, Michigan
Co-Producer, 2013 to 2014
Girlie-Q Productions, Chicago, Illinois
Production Board Member, 2008 to 2010


Let’s Get In Touch

For booking or press inquiries, please contact me here.

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