The Scoop: Shannon Tebb, CEO of Shanny in the City, provides practical assistance to relationship-minded singles in and around Toronto. She offers boutique matchmaking, dating coaching, life coaching, and fashion consultations to build her clients up and make them feel comfortable and confident in the dating scene. As part of her business, she has run mock dates, gone on shopping excursions, and even acted as a personal wingwoman to support singles wherever they need guidance. Her invaluable expertise has led many clients to their happily ever afters. In fact, her matchmaking firm currently boasts a 74% success rate. Daters in the field can rely on Shannon to have their backs as they navigate the dating scene and form budding relationships.

In the 2005 romantic comedy “Hitch,” it’s a big secret that Will Smith is working as a dating coach and personal wingman to single guys in New York City. He operates under the radar so women won’t know he’s whispering tips in men’s ears. But what exactly is so bad about that? Athletes are allowed to hire professional trainers. Models can hire dietitians. So why can’t singles seek professional assistance too?

Photo of Shannon Tebb, CEO of Shanny in the City

Matchmaker Shannon Tebb said the movie “Hitch” inspired her to enter the dating industry.

Despite the negative stigma, seeing a dating coach or matchmaker is a good sign that someone is committed to improving their dating results and attracting the right partner. As a boutique matchmaker and wingwoman, Shannon Tebb is on a mission to make professional dating services a more acceptable and enjoyable resource for singles in Toronto, where she’s lived for 12 years.

“It’s nice to have a professional to help you through dating,” she said. “I’m there to work out the kinks before you go out. I show singles how to interact with the opposite sex and get comfortable in a social environment.”

Since 2010, Shannon’s concierge dating service, Shanny in the City, has offered hands-on assistance and knowledgeable advice to singles who are ready to get in a relationship but don’t know how to go about it. She provides concrete guidance to help her clients put aside their nerves and fears so they can put their best foot forward on first dates, at singles events, and in other social situations.

As a dating professional, Shannon is all about making a lasting difference in her client’s love life. She doesn’t just deliver a good catch — she shows her clients how to fish for dates themselves during wingwoman nights on the town. Whether her client is newly divorced or never married, she gives them the tools they need to embark on a worry-free and values-driven dating experience.

“People use matchmakers because they’re busy professionals who don’t have the time to go online and want a bit more privacy,” she said. “I want to get rid of the stigma that it’s not cool to use a matchmaker.”

Shannon Tebb Helps Singles Get Back Out There

One way Shannon makes her matchmaking service stand out from others in the business is by accompanying her clients to afterwork socials, networking events, and charity events. Her wingwoman service includes three hours of mixing and mingling with a professional by your side. Clients can choose the venue, and Shannon will assume the role of a friend who can break the ice, make introductions, and slip away if the couple starts to hit it off.

This wingwoman service is the only service of its kind in Toronto. No dating professional in the area puts as much energy into seeing singles get new relationships off to the right start.

“I absolutely loved the wingwoman service that Shanny in the City provides,” wrote a 38-year-old single woman in a testimonial. “Shannon is fun and brings up your confidence. She organized the evening perfectly, and I met people I never would have met on my own.”

Screenshot of Shanny in the City's homepage

Shannon’s wingwoman service helps daters break the ice and feel more confident in social settings.

Shannon said going out together is a fun way to get singles out of their shells. “They have a blast,” she said. “We have such a good time.”

Throughout the evening, Shannon offers tips on how to make an approach, how to read body language, and what to talk about with a new love interest. She does all she can to keep her clients’ energy up so they feel comfortable starting conversations and flirting even without her help. Shannon takes individuals as well as groups out on what she calls “Wingnights.” These consultations offer the practical help singles need to improve their social and dating skills in real time.

“The intent of the wingwoman night is to make connections, get phone numbers, land dates, and all of that,” she said. “It gives singles the push they need and something to look forward to. It increases their confidence and gives them hope.”

Shopping Excursions, Mock Dates & Other Resources

In addition to boutique matchmaking, Shannon gives singles a range of add-on services to choose from, so they can take their dating games up a notch. Singles can hire her as a matchmaker or wingwoman, and they can also seek her advice as a dating consultant or life coach or book a styling or shopping session.

Her dating consultations typically last an hour and include a deep dive into the strategies and tactics that lead to romantic success. She can focus on particular weak points in her client’s love life — for instance, maybe he or she is having difficulty getting a second date — or she can provide a general overview of how to act in the modern dating scene. Shannon’s hourly rate for a dating consult is $175.

Sometimes Shannon arranges mock dates with her clients so she can see them in action and assess their date conversation, date attire, body language, and date follow-up techniques. She said she often provides homework and exercises that keep her clients learning and growing after their one-on-one session is over.

Photo of a couple hugging

Shannon has coached over 500 singles in person, on the phone, and via Skype.

Shannon’s life coaching service is broader and more about personal development than straightforward dating coaching. Shannon charges $175 for an hour-long session dedicated to imparting strong life skills, including communication, self-awareness, and active listening. All these skills are important in relationships, but they can also help people in other areas of life.

Shannon told us she also organizes personal shopping sessions for clients who are looking for trendy date attire. The dating expert picks out clothing that brings out her client’s style and makes them feel good about themselves. It’s important to make a great first impression on a date, and Shannon’s fashion tips can help someone do just that.

“I help manage your dating lifestyle,” she said. “I do all the work for you behind the scenes and see that you get the results you want.”

Taking the Stress Out of the Dating Experience

Shanny in the City’s matchmaking service boasts a 74% success rate. Her boutique screening and matching process yields great results and has solved the dating worries of many busy professionals ranging in age from 25 to 55.

Shannon told us she has worked with singles facing many different dating challenges. “I have worked with millennials who don’t know how to talk to a date and baby boomers who don’t know how to text,” she said. “People are forgetting how to connect authentically, and that’s why I do what I do.”

“All I can say about Shanny is she’s the real deal.” — A satisfied Shanny in the City client

Whether she’s acting as a middle(wo)man between a fledgling relationship or preparing singles to succeed on a dating site or app, Shannon caters her approach to the needs and personalities of her clients. She does all she can to take the stress and work out of dating, so singles just have to show up and enjoy themselves. By fostering a stress-free environment, she helps singles build self-esteem and carry on in a positive direction.

“I used Shanny in the City to find the love of my life,” said a 42-year-old client. “Shanny understood what I was looking for in my partner, and she delivered!”

“Shannon helped me out tremendously,” said a male client in his late 40s. “I improved myself and changed for the better…I improved my overall image, and I’m now dating someone who is important to me.”

Shannon Supports Clients Every Step of the Way

Shannon, much like Will Smith’s character Hitch, supports daters who want to find love but don’t know where to look or how to create romantic opportunities themselves. Her comprehensive, hands-on services empower singles to grow into more confident, attractive, and capable daters both online and offline.

This Toronto-based dating expert arranges introductions, offers sage advice, organizes learning exercises, and accompanies clients out on the town, all in hopes of raising the caliber of dates in her area. From start to finish, Shannon’s thoughtful guidance helps singles of all ages improve themselves and increase their odds of finding a perfect match.

“It’s really all about connection,” she said, “and feeling good about yourself. You have to ask yourself, ‘Am I ready to date?’ Just start slow, get comfortable, and have fun with it.”

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