By Lauren Toffan

Spring is just around the corner and the warm weather will surely draw out your inner social butterfly. Unless you are one of the brave few who have continued to exercise those social skills and date new people throughout the winter, your pick up lines are probably in need of a proper tune up. Shannon Tebb, Founder of Shanny in the City, can help guide you in the right direction and warm up the charisma that’s been hibernating all winter long.

“People are afraid to talk to strangers, which often limits them of making new friends and even chatting up potential mates” says Tebb.

For most single Torontonians, pre-marriage or newly divorced, the concept of meeting someone new or stepping outside of your comfort zone is more debilitating than paying your back taxes. Tebb says, it doesn’t have to be. This is why she is offering another service: The Wingwoman service. To help divorcees or singles who may not have a singles network of friends to venture out with.

Shannon Tebb, originally founded Shanny in The City, a boutique Matchmaking and Dating Consultanting service in 2010. In recent years she has provided the Wingwoman service to clients in need of ice breaker tips for dating and even networking situations. By hiring Tebb as your Wingwoman for the evening, you will learn how to skillfully initiate that first conversation, assess your surroundings and pull yourself out of that shell, you may not even know you’re in.

Through a confidential, pre-consultation, you are encouraged to open up about your interests, hobbies and relationship desires with Tebb. This way, you can discuss the personal blocks you may have when you are out on dates or in social situations. Tebb will then offer constructive feedback to improve your social etiquette, as well as helpful tips to spruce up your appearance, all with the intention of making your Wingwoman night, the greatest bang for your buck.

On your night out with Tebb, she will provide a strategic plan for your evening, which includes a set time line of venues and goals to break the ice, strike up conversations and increase your awareness of social cues from those around you.

“Most women don’t even realize when someone is checking them out,” says Tebb. For some, this may sound like the work of a best friend, but Tebb says, “With a friend, it can become competitive.” The difference is with a hired Wingwoman by your side, the evening is about you. The role of the Wingwoman is to make an easy introduction between you and your person of interest, help keep the conversation at a comfortable level and ensure you are satisfied with your newest connection. Ultimately, Tebb wants to see you grow and meet someone authentically.

“People need to start talking to one another in this city,” says Tebb. “The loneliest people are afraid of saying ‘hi,’ but that person is just as lonely as you.”

Despite her small town charm, Tebb has worked and lived in the city of Toronto for years, therefore she knows how to navigate personalities and big city attitudes. “The key is to act like a tourist in your own city,” she says. With years of working as a Life-Skills Coach, Dating Expert and Matchmaker, Tebb has coached over 500 people and has matched over 50 long-term couples.

If you want to be inspired by love then work with Shanny. I knew what type of person I needed in my life but I didn’t exactly know how to find him. Shanny did the job and was enthusiastic, positive and dedicated to love is how I would describe my experience of her services. I’ve been dating the man of my dreams for almost a year and I’ve never been happier. A big thank you from the happy heart.


After recently coming out of a long-term relationship, I discovered Shanny in the City from a friend and contacted her right away. Not only was she professional and organized but dealt with my situation and questions on the next steps towards dating again in a knowledgeable and experienced manner. Her advice was spot-on and I found I was dating almost immediately and not only using her help to find dates but on how to work on my before-and-after dating experiences as well. I would highly recommend her to anyone who is recently new to the dating arena or is looking to hone their skills with dating in general.


By hiring Tebb as your Wingwoman, you will be guaranteed a pre-consultation, a minimum of two hours, your venue of choice, feedback and a date report, all for a fee of $350. For more information, please click on the link below:


T: 416 885 2696

I: @shannyinthecity