Sex & the 6ix: Connor & Jenna

Sex & The 6ix is our new weekly Sunday dating column in collaboration with a dating expert and matchmaker. Every week watch two people get to know each other and predict if the relationship will bloom or if it looks like an epic fail. We send two people out to a hot spot to enjoy dinner on us and see if we can make a love connection! 

Sex and the 6ixMeet our matchmaker:

Shannon Tebb, entrepreneur and creator of Shanny in the City, has worked as a Matchmaker and Dating Consultant since 2010. She has been featured on various radio shows, and offered her expert opinion for articles in the Huffington Post, The Star, Metro, Eligible TV, Oh So Cosmo, KISS 92.5, CBC Radio, and was the spokesperson for

Interested in being one of our daters? Shanny is looking for genuine candidates that are interested in finding love in this oh so busy city!

Fill out the form that applies to you and we will set you up with a potential perfect match! With Shanny’s expertise, we hope we can help you find love in the 6ix – or at least enjoy a nice meal on us. After the date we ask for a quick feedback session to gain insight as to how the date went and encourage you to keep putting yourself out there!

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Now onto this week’s date…. Meet Shanny’s match:

Sex & the 6ix

Shanny tells us why she matched these two up:

This week I wanted to switch it up a bit and play matchmaker with the millennials.

Jenna and Connor were our youngest applicants for the Sex & the 6ix blind date and were a bit shocked when I offered them a dinner on us.

Who knew that a 21 year-old guy could be interested in a long-term relationship? When I was that age, I was glued to the TV watching re-runs of Beverley Hills 90210, not trying to find a committed relationship. And now we see the “hook up” culture in full force leaving little room for the relationship chat. Connor, a business coach and entrepreneur, he isn’t your average millennial and finds it tough finding mature girls in his age category that are “keepers”. Although, Jenna was looking for something more casual, I felt that she would be smitten with Connor, which is why I wanted these two to meet.

One common interest they both shared in their profile was checking out a hot new restaurant on a Friday night rather than a typical movie date. Jenna said that she was attracted to an athletic entrepreneur and ideas guy, which is exactly who Connor is. Connor looks for intelligence in a match and appreciates a take-charge woman. Being in marketing, I felt Jenna resembled this girl boss persona, and also rocked the cute librarian look behind her black rim glasses.

Given that these two are close in age and have similar interests, did sparks fly? Let’s see if these two will make a connection over margaritas at Fonda Lola.

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Sex and the 6ix

After interviewing both Connor and Jenna, Shannon’s expert opinion is…

After chatting with Connor and Jenna it was evident that one was looking forward to a second date while the other was disengaged with the idea. It’s unfortunate that a second date won’t be happening anytime soon. The date ended after an hour and a half, and there wasn’t even a goodbye hug. I think it’s fair to say that these two both have experienced different things from one another even if both are close in age. One is an avid traveller, while the other has yet to fly leaving little substance for conversation they would both enjoy.

Although this wasn’t the perfect match, I think they both enjoyed the food at Fonda Lola and got some practice dating and figuring out exactly what they are looking for.

We wish both our daters success with future love connections!

Related Link: Brittany & Ken

What do you think of this week’s date? Let Vv Magazine know in the comments below, or tweet us @ViewtheVibe.

Shannon Tebb

Shannon Tebb

Shannon Tebb, entrepreneur and creator of Shanny in the City, has worked as a Matchmaker and Dating Consultant since 2010.
Shannon Tebb

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