Jessica O’Reilly is a teacher, author and sex educator whose doctoral research focused on brief interventions designed to improve teachers’ knowledge and comfort level with sexual health education in Ontario. Her practical relationship advice reaches millions each month via mainstream media outlets and she travels extensively across the globe to work with couples (including royalty and presidential candidates) to transform their relationships from good to great. Her passion, however, is inclusive classroom-based sex & relationship education and she continues to volunteer with teachers, students and parents to promote programming that empowers youth and produces positive health outcomes. Catch Jess on Global Television’s The Morning Show each week at 8am.
What do I do best?
I try to entertain audiences and make them laugh so they don’t even realize they’re learning. Laughter is key in my field to assuage discomfort.
I really care about helping people to improve their relationships, as I believe that our closest relationships are the keys to happiness and fulfilment. There is no one-size-fits-all approach, but I try to marry data with practicality to create programs that inspire and facilitate behavioural change — in and out of the bedroom. It’s one thing to convey useful information, but my programs and podcasts are designed to put theory into practice so you can have a happier relationship without overhauling your whole life — you can make small changes in just 60 seconds a day.
What makes me the best version of myself?
In my practice: I try to make people comfortable with topics that are often difficult to discuss. I also try to approach a rather contentious topic with humour, sophistication and without judgment. If we dropped the judgment around sex, we wouldn’t need people like me.
In business: I make connections — between people, brands and strategies. I’m an open book in terms of contacts and I’m happy to share.
What are my aspirations?
Personally, my greatest aspiration involves adopting a child with my partner and learning to be a great parent.
In business, I want to reach more people to have a greater impact. We’re currently undergoing a rebrand to help more people have happier, more fulfilling relationships. We’ll be launching “Happier Couples” in a few months…My goal is to make my program more accessible to a wider audience via video courses. Currently, I work with a tiny (privileged) section of the population, but I’d like everyone to be able to access this information, so that they’ll feel better about themselves and happier in their relationships. And I also want my husband, Brandon, to get more involved. People seem to like him:)
My Biggest Success?
My relationship with my partner (husband) is my greatest accomplishment. We’re far from perfect, but we’re really happy. We’ve been together nearly 17 years and I look forward to growing old together. It’s the most comforting and exciting feeling to look forward to the future with Brandon.
My Most Challenging Moment?
I struggle almost every day with the subversiveness of the work I do. I want to quit often. I get a lot of hate mail — mostly in response to my TedX Vancouver Talk, Monogamish.
When someone tells me they hate me or criticizes my appearance, my voice, my viewpoints or my work, it’s tough to keep going. Being in the public eye isn’t particularly appealing to me, but I’ve built my brand via traditional and digital media, so it’s a bit of a contradiction. On one hand, I love my work and all the associated benefits , outcomes and opportunities; on the other, I find the part that involves being in the public eye (especially on the digital side) exhausting at times.
I’m really trying to help people. I don’t have all the answers. I know I’m not perfect. But I’m very good at what I do and I know I make an impact, because I see it in my clients’ feedback and relationships. The tough part involves remembering this and pushing through when it feels like everyone is angered by a simple article on gender, vaccinations or relationships.
Do good and smile at strangers — especially the ones who tend to be ignored (older folks, people experiencing homelessness).
My Favorite People/Role Models?
My cousins Mike & Denise are my personal role models. They’re just really happy. And so are their kids.
My Favorite Places/Destinations?
Goldeneye in Oracabessa, Jamaica is one of my favourite spots. My mother is from Kingston, Jamaica, and Goldeneye might be the most beautiful spot on the island.
My work has taken me to some very interesting places — Beirut, Manila, Instanbul, Rome, Split, Bucharest, and Kiev top my list of cities I’ve really enjoyed and hope to visit again sometime soon.
But overall, my favourite spot (when it’s not too cold) is my neighbourhood of Corktown, downtown Toronto. I have incredible neighbours and somehow we’ve cultivated a supportive small-town community in the big (sometimes) cold city. Whether you need milk, a babysitter, a crockpot or a flapper costume, one of your neighbours has you covered.
My Favorite Products/Objects
The Vitamix. It changed my life. I hate vegetables, but I’m happy to drink them mixed with fruits.
The Briggs & Riley Baseline International Carry-On. I can travel for up to two weeks with carry-on only with this great little piece of luggage and it has a lifetime warranty with no questions asked.
My Current Passions?
Brandon, my partner.
Woke folks & kind people.
Young people. I volunteer in classrooms to teach sex & relationship education and I train teachers to deliver effective programming. Young folks deserve accurate information and I want to be a part of the solution.
The perfect cortado (even if I’m judged for drinking decaf). Full-bodied red wines.
Air travel. The moment I see planes landing and taking off at the airport, my mind and body are set at ease.
My work. I’m really excited for this new brand we’re launching for two reasons: I know we can really help people build better relationships. And I’m thrilled that Brandon will be coming on board to work with me. We’re building a brand that focuses on both people and profits with a social giving component formally built into our business model.
Aside from Happier Couples, I’m passionate about a number of other ventures I’m working on: a few in digital tech, health tech, entertainment and real estate. I like variety and the mix of projects keeps busy, motivated and always on my toes.