About Dr. Jess
Jess O’Reilly began working as a sexuality counsellor in 2001 and she has never looked back! Her PhD studies involved the development of training programs in sex education for teachers and her education and undergraduate degrees focused on equity and sexual diversity.
Her training includes courses in counselling skills, healthy relationships, resolving sexual concerns, sex education, clinical sexology, sexual development, sex and disability, group therapy and Cognitive Behavioural Therapy.
Alongside her academic and television credits, Dr. Jess is also an accomplished author with three best-selling titles. Her latest, The New Sex Bible, has received rave reviews from professionals and clients alike and her first book Hot Sex Tips,Tricks and Licks is in its fourth print! Look for her monthly column in Post City or catch her on Tuesday mornings on Global TV’s The Morning Show, Wednesdays on 102.1 The Edge and Saturdays on PlayboyTV.
Dr. Jess’ work experience includes contracts with school boards, social services agencies, community health organizations and private corporations. A sought-after speaker, her sessions always attract a full-house at conferences and entertainment events alike.
Check out more about Dr. Jess!
Dr. Jess O-Reilly Plays 20 Questions with SHA!
“You’re the ultimate expert in your own sexuality and pleasure.”
The Sexual Health Alliance (SHA) is centered around providing Provocative Dialogue and Radical Collaboration. What would radical collaboration look like for you?
To me, radical collaboration involves sharing my business and working with industry peers who don’t have the same opportunities and privilege as I do. This might involve referring out services to folks who are better qualified to speak on specific issues (e.g. Black sexuality, sex for people with disabilities). It also involves sharing resources, insights and experiences for low/no cost to those in financial need. And at times, it involves sharing the financial profits on specific projects (e.g. collaborating on products like books, video courses and speaking engagements).
As a prominent sexuality professional, you have made a wonderful career as a sex educator. What would you recommend to young educators or therapists wanting to follow in your footsteps?
Ask for help. Don’t be afraid to reach out and ask for the support of your peers and potential mentors. Many of us want to help and if you’re very specific with your request (e.g. Can I pick your brain? is too broad, but Could you look over this introductory paragraph of my book proposal? is more manageable), you’ll probably receive a positive reply.
What book(s) are you reading right now?
I’m rereading Life and Death in Shanghai.
What’s the most important thing you talk about with your clients?
Custom-designing their relationships. There is no one-size-fits-all approach and you can make almost any arrangement work if you’re not burdened by social pressure.
What are the top 3 items on your bucket list?
1. I’d like to build an affordable housing building in my hometown of Toronto and see if we can grow the project to be sustainable; eventually, I’d like to continue to build additional units.
2. I’d like to adopt a child.
3. I want to live to be 100+.
One of our goals is to provide all therapists and healthcare providers with high quality sexuality training because they often receive little to no education in sexual health. What is the most important piece about sex that you want all providers to know? What would you want them to incorporate into their practice?
I’d like every professional to understand that our personal sex and relationship lenses can be completely irrelevant to our clients/patients’ lived experience. This doesn’t mean that our work isn’t shaped by personal experience, but simply that we need to be aware of our own biases and limits. And we need to be more aware of our layers of privilege related to race, gender, income, education, ability, nation of birth, relationship status, social status and professional roles.
What are your top 2 books that have influenced you and why?
Give and Take by Adam Grant. This was an affirming read, as he shares stories and data suggesting that good people do finish first in life and in business.
Our Bodies, Ourselves. I read this many, many years ago when I was in school and it offered such an important perspective on so many different topics. I know they’ve updated it since then and I’ve been meaning to go back to it and read the new version, so thanks for the reminder!
What is bad advice you have heard other people in our field give?
I still hear professionals talk about other cultures and countries as though they’re monoliths that they understand because they worked with clients from a specific culture or they lived in a place for a few months or years. If you’re not a part of a group or culture, elevate the voice of someone from that group instead of speaking for or about them. Nothing about us without us.
Who is your sexual role model?
That’s a great question! I’m not sure I know enough about anyone else’s sex life to call them a role model. Marla Renee Stewart is a general role model — personally and professionally — and I believe she has very happy relationships — sexual and otherwise.
SHA utilizes social media to reach our members as well as to find new sexuality content and research, how do you think social media has influenced our culture’s sexuality?
I’m so thankful for the reach and impact of social media. Putting the power of broadcast into individual hands (instead of allowing it to rest in the hands of a few corporations) has shifted and broadened the content we consume. Accounts like @SexPositiveFamilies, for example, disseminate essential information that mainstream (old) media would never have touched. Research shows that digital consumption and connections can foster digital empathy, galvanize support, create feelings of belonging and build community. Of course, social media is still owned by a few corporations and we don’t have access to how they disseminate our posts, so we have to be mindful that new media also has its limitations.
Our team finds podcasts, youtube and other social media platforms sometimes more educational and useful than traditional models. Do you think social media should have a place in formal training, and if so, how much?
There are accounts that offer high-quality, evidence-based information and there are also powerful accounts that provide misinformation. I think it’s important to analyze media (including social media) in all training and examine messages and biases. Part of all learning processes involves developing and tuning our critical thinking skills and I believe that we can certainly use social media as both a lens and subject.
What made you create your Happily ever after approach to working with couples?
I work primarily with folks who run or own businesses. They’re passionate about their work and they claim that their family is the most important aspect of their lives, but they don’t always act like it. Our Marriage As a Business approach involves applying business practices and acumen to intimate relationships. This might entail hosting board meetings (relationship check-ins), building a support team (e.g. therapists and babysitters), respecting timelines (e.g. showing up to dinner on time), planning ahead (e.g. carving out time weeks, months or even a year in advance).
As a Canadian born, Chinese-Jamaican and Irish by descent person, what has been the most challenging aspect of working in this field?
My gender, appearance and (perceived) ethnicity provide me with both privilege and challenges. As a woman talking about a sensitive topic in the public eye, I draw considerable criticism, harassment and personal attacks — on Instagram, Twitter, Facebook, my website contact form and even on LinkedIn. I ignore most of it, but sometimes it does feel like death by a thousand paper cuts. Luckily, I have a lot of support too. And I love life and I’m lucky in so many ways, so I try not to expend my energy on the harassment.
Where is your next dream vacation?
I’m not sure. I have a big birthday coming up in February and I’m deciding between Tuscany, Japan and Jamaica. Help me choose!
What are 2 of the most important things you do everyday?
If I’m home, my partner makes me a decaf macchiato or cortado in a small double-wall glass, which I try to take the time to enjoy without reading, working or scrolling. The glassware and all the details add to my enjoyment; he weighs the beans, grinds them with a beautiful manual grinder, pulls the shots at the right pace and warms the milk to the perfect temperature. It sounds pretentious, but I don’t care, because it’s delicious.
I don’t have many rituals, because I’m on the road most of the time and everything is always changing. But I do make time to enjoy myself wherever I go — even if I only have a few hours in a new city or country, I try to walk to a local third-wave coffee shop or market to get a pulse on local life. If I have time for lunch, I always treat myself to something delicious. Food is my love language and working in the food industry is a part of my family background.
What’s your favorite place you’ve traveling to for you job and why?
It’s hard to pick a favorite place, but Istanbul certainly stands out as a highlight. The people are always so warm and gracious. The rich culture, history and architecture overwhelm me. And the food is so delicious and varied. I hope to return again soon.
What’s the most challenging aspect of being in business with your partner, Brandon? (They are married)
Me. I’m the most challenging aspect. He’s much easier to work with.
We don’t work together full-time. He helps out to co-host the podcast, but he has his own unrelated business that keeps him very busy.
The most challenging aspect relates to my travel schedule. I love travel and I love flying and dealing with the unpredictability of new surroundings, but I do miss being physically together. This was a challenge for several years, but he travels with me far more often now, as he has more flexibility with his business.
What’s your favorite story to tell?
I’m a storyteller. As they say, a story doesn’t have to be true to be good. Ha!
But here’s a true one:
On a flight from Denver to Albuquerque a few years ago, a guy threw up all over me as the plane landed. Instead of just vomiting, he tried to keep it in his cheeks and so the trajectory changed and it sprayed everywhere — all over me and in the hair of the couple in front of us. People were dry heaving all around us and I was just hoping that no one else would vomit. I remember thinking that if one more person vomits, the whole plane is going to become a vomit comet. I don’t know why I picked that story, but it just popped into my head.
If you want something sexuality-related:
One time I was at a sex club and two people high fived on the bed next to us while exclaiming, “Oh yeah. This is so hot! And it’s a great workout, so we can skip the gym tomorrow!”. This was their dirty talk and it got them all riled up, but it killed the vibe for me and some of the others in close proximity.
Another time, as lady who was 7+ months pregnant stopped me and asked if I could help her figure out a good position for DP (double penetration) given her big belly. This was a time when I was reminded that they definitely don’t teach you everything you need to know in school.
Your bio says you like airplane turbulence! Can you tell us more about why you like it?
I just love airplanes — I love flying in them, talking about them, reading about them. And I like the physical thrill of a little turbulence — especially in a bigger plane. I will reroute to fly on a cool plane (e.g. the 787-9) and I hope to train as a pilot someday.
Being trained in sex & disabilities, can you give us some tips on why discussing disability is important?
All sexual health education needs to be inclusive and this includes talking about sex as it relates to race, ethnicity, gender identity, sexual orientation, relationship arrangement, income, and disability. I facilitated sessions on sex and disability early on in my career and now I’ve learned that I should pass the mic and advocate for paying opportunities for fellow sexologists who have disabilities. There are many qualified folks who simply don’t get the same paid opportunities as I do because of ableism.
When we leave folks with disabilities out of the conversation, we reinforce inaccurate stereotypes and put them at greater risk, as sexual health education produces positive health outcomes regardless of whether or not you have a disability.
What's an important take away from your new book The New Sex Bible?
Do what feels good for you. Don’t worry about what the experts or your friends have to say. You’re the ultimate expert in your own sexuality and pleasure.
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