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Our Story

Like the classic girl groups of the 90s, Classic Affairs by Jenna is made up of an incredible group of woman who share one common goal; Elevating your Wedding experience. Founded in 2015 and led by Creative Director, Principle Planner and Florist - Jenna Lipman, Classic Affairs by Jenna's team will help set the tone for your custom wedding experience. 


Fast forward 8 years and we have grown to a core team of 4, and with an expansion into the floral design side of the industry we really are a one-stop shop for all your event needs. From Planning, and execution to design details, florals and decor rentals. We believe that providing personalized and attentive service, excellent communication and creative ideas is where we shine! Let us elevate your wedding to the next level! 

Get to know our incredible team below!

Meet the Team


Nicole Gregory

Creative Director, Principal Planner & Florist

I'm Jenna, Creative Director, Principle Planner and Florist at Classic Affairs By Jenna. Weddings, floral design and event planning is not only my career but my passion! There is no better feeling than knowing I have made my clients dreams come true on their big day. Graduating from the Toronto Metropolitan University's (Formerly Ryerson) Hospitality & Tourism Management program through the Ted Rogers school of management and having worked in the hospitality industry for over 12 years, I have successfully executed over 600 weddings. I am also a certified wedding and events planner through the WPICC. With a background in event/venue management, wedding planning and floral design, I look forward to working with each and every client to successfully bring their wedding day vision to life! In my down time you can find me at the beach, walking my furbaby Pepper or planning my next vacation. I love to travel!

Senior Wedding Planner & Director of Operations

I'm Nicole, Senior Wedding Planner & Director of Operations at Classic Affairs By Jenna. I am a Fashion Management & WPICC graduate with a love for everything Weddings! Having previously worked in the bridal industry as well as wedding planning, I have seen many different sides to the wedding industry and have a lot of knowledge when it comes to all things wedding related. Ever since I was a little girl, I have loved everything that has to do with weddings. I grew up watching Say Yes to The Dress and Four Weddings. Fun fact- I actually worked at Kleinfeld Canada for a little bit and it was a dream come true! When I am not onsite, you can find me on the back end working on all things social media related. I love being able to share all those special moments we see with everyone that follows us! When I am not working, you can find me spending time with my boyfriend aventuring while blasting country music, shopping or travelling.  

Jenna Lipman

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Karleece Lapointe-Kumar

Senior Wedding Producer

I’m Karleece, one of the Wedding Planner's at Classic Affairs by Jenna.

I am a WPICC graduate and have a background in Fashion Design and Apparel Production. I am newer to the wedding planning industry however, I have many years experience helping brides and bridesmaids find the perfect attire for the day of. There is such a special feeling you get when you help someone plan and execute such an Important day! When I’m not working, you can find me spending time with my pets, travelling, and shopping!

Alana Martin

Lead Wedding Planner


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Jemeika Jackson

Associate Wedding Planner


Rachel Sedore

Associate Wedding Planner


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