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Will You Be My Bridesmaid? How I Popped The Question

If you read my blog post a few months ago, you know that Justin and I have decided to postpone our wedding (wahh!). We got engaged four years ago and I pretty much knew from the beginning who was going to be in my bridal party. I really wanted to ask my bridesmaids the moment we got engaged, but I wanted to make it special for them as all of these ladies are SO important to me! Fast forward to four years later, I finally popped the question, “will you be my bridesmaid!” Today, I’m sharing all of those details with you below!

Before I kick this post off and tell you who is in my bridal party and how I asked them, I will be the first to admit that I have a rather large group of bridesmaids!! There are so many amazing women in my life that I just couldn’t imagine saying “I do” without all of my favourite gals standing next to me. It just didn’t make sense to cut that number. All of these ladies play such a different role in my life, some of them I have known since day one and others I have known for a short time, but they all mean the world to me.

My Bridal Party

Let’s start things off with who I asked to be my maid of honour! Can you guess who I picked!?! I’ll give you a hint; I picked not one but TWO ladies!! I know it may seem unconventional, but my entire engagement has been a bit unconventional. I consider both of these ladies to be my best friends, soul mates, and I have a completely different relationship with both of them. I couldn’t pick just one. So … who did I ask to be my maid of honour(s)?! I asked Tori AND Sam!!

Jillian Harris Cousin Tori and SamJillian Harris and Tori Wesszer


Tori has been in my life since the day I was born. She’s not only my cousin but someone I consider as a sister. She is my business partner and one of my best friends and I just couldn’t picture doing this without her! Growing up I idolized her so much, I always wanted to do everything she was doing.

Tori and I lived across the street from each other in our mid-twenties, both single with broken hearts, but we got through it together. She always has been my true north star when it comes to doing what’s right and thinking of others. As you know, Tori and I ventured out and created the Fraiche Food Full Hearts cookbook, and I couldn’t have done that without her!

Ps. If you’re looking for a good laugh, Tori, Sam and I were featured in a TMZ video, I’ve added the link below … you can thank me later … LOL! 

Jillian Harris and Cousin Samantha Thompson


Sam and I have had such a unique relationship. I not only consider her my best friend but my soul mate (sorry, Dustin!). Whenever I have something on my mind I know that I can talk to her about anything. Even better, we can also talk about nothing at all. Some of our best times together are just being in the presence of each other with a glass of wine in hand. I truly think that some of the best friends are friends that you can just be in their company and not have forced conversations with. We have also had some very funny moments together … if you haven’t seen the TMZ video of Sam, Tori, and I then you are in for a treat! 

Now that you know who my maid of honours are, I wanted to take a moment and introduce you to the rest of the wedding party … well, my side at least … LOL!

Jillian Harris and Cousin Stephanie


I’ve known Steph since the day she was born! She and I grew up together and some of my fondest memories are with her and her sister, Sam. Steph is SO funny, has a heart of gold, and she is always up for anything! I look up to her in so many ways, she is an amazing mama and an entrepreneur. If you haven’t seen some of her photos make sure to check them out here!! 

Jillian Harris and Bridesmaid Karissa


I’ve been friends with Karissa since our first birthday. My grandma and grandpa lived next door to Karissa and her family, which (lucky for me!) meant I got to go over to her and her sister, Karrie’s, house after school most days.

Karissa and Karrie’s parents raised me like their own, the first time I ever dabbled into wine was at their place … LOL! We have grown up together, travelled together, and had so many firsts together. She is the so kind, patient, and just the most loving human being! Even though Karissa is the kindest sweetest person you have ever met, we have some pretty wild and rebellious memories together. 

Jillian Harris' Bridesmaid


Shannon and I have known each other since elementary school. Shannon, Karissa, and I have had a really strong friendship and bond our whole lives. We have done many first together, from sneaking out as teens, taking our parent’s cars when they weren’t looking, first boyfriends, learning to drive, being roommates, road trips, camping trips, and trips around the world. I love her beyond measure! 

Jillian Harris Bride Tribe


Angela and I met in college and she is my funniest and most unique friend. A lot of you that follow me on Instagram call her my “new friend” … LOL!! She is really not a fan of being on Instagram, so when I happen to catch her on a story or a post you all think she is a new friend but she has been in my life for quite some time now! The thing about Angela is, she doesn’t force her feelings, she doesn’t pretend to be anyone that she isn’t. She is SO goofy, funny, and so dependable. My steady eddy best friend. LOL!

Jillian Harris and Make-Up Artist Kaitlin Hargreaves


Kaitlin and I have known eachother since Love It or List It and she has been my Makeup Artist for 8 years now. If you don’t follow her on social media, what are you waiting for?! LOL! She’s not only hilarious, but she is such a talented artist and creates the most stunning watercolour paintings! She never puts up with my sh*t and I love that about her. She is someone that knows me almost better than anyone.

Jillian Harris and Shay Merritt 2015


Shay has been with me for 7 years now!! She helped me build this business to where it is today, and she even helped pick out my engagement ring. She has been through so many ups and downs with Justin and I. Even though she started as my assistant, she basically runs the company now. She has been there with me through not only business-related endeavours but personal ones as well. She was there when both Leo and Annie were born, she has helped plan their baby showers and family get-togethers. Even though she is a business colleague, I felt like I needed her up there with me because she has been a part of mine and Justin’s relationship since the very beginning.

Bridesmaid Boxes

Now, changing gears a little and moving on to the fun stuff! Let me share how I asked these ladies to be in my bridal party!

I had originally planned to ask all of my bridesmaids to be in my bridal party in person, but due to COVID I was only able to ask a few of them in person and fortunately, I was able to catch some of their reactions on video (make sure to give it a watch, below!).

I prepared a beautiful bridesmaid box for each of the girls to ask them to be in our wedding party. I had so much fun building these bridesmaid boxes, from the planning to executing and everything in between! I wanted it to be filled with a few items that I personally loved and that also showed these ladies just how much they mean to me (and to hopefully win them over to saying “yes!” to be my bridesmaids!). LOL!

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Melaine Auld Bridesmaid Rings

The hero item in the box is a stunning ring from Melanie Auld! They are 14k yellow gold with a Blue Topaz Center stone flanked by a diamond on each side. I really wanted this piece to incorporate “something blue” as blue represents love, purity, and fidelity. I also wanted the design of the ring to resemble a heirloom ring to wear for years to come and pass down to other generations (eventually … LOL). It’s also my birth stone so thought it would be nice for my bridal party to share that with me.

Lamarca Prosecco Mini Bottle
The Cake Mama Custom Cookies
Will you be my bridesmaid gift box

The other items that I included in the box was a mini bottle of Lamarca prosecco, a scrunchie from Chelsea King, and adorable cookies from The Cake Mama. The last item in the box was a very heartfelt card from Minted, what I LOVE about these cards is that they all included a picture of me and each of my bridesmaids/maids of honour and included a little heartfelt letter. These cards were such a great addition to the box, they are relatively inexpensive and completely customizable, which I loved!

Custom Bridesmaid Card From Minted

Stay tuned for another blog post on who Justin’s groomsmen are and how he asked his buddies!



Leave a Reply

  1. I’m 27 weeks pregnant and you can’t do this to me!!! I balled my eyes out reading the blog and watching all the reactions!

    Such a lovely way to express your love to your friends and family!

    I can’t wait for the posts about the wedding day (whenever that will be❤️)

    1. Aww! Congrats mama!! So happy to hear you loved the blog, I held back tears watching the videos for the second time too! xo

  2. SO beautiful! I smiled through the whole thing, I can see the love you and your bridal party have for each other and I think I loved watching this so much because it’s totally relatable to my own group of friends! We all talk about being apart of each others day (when the time comes) thanks for giving me such great ideas 😉

  3. Ohhhh my goshhhhhhh! This box is so beautiful and thoughtful. Way to make me cry on a Wednesday afternoon.
    So so sweet. I can’t wait for your wedding day!

  4. Yay! I held off on sending mine when I saw your sneakpeeks on Insta awhile back! Such beautiful, thoughtful boxes! 🙂

  5. Beautiful bridesmaid box! So sweet brought tears to my eyes! You stated you sent nine boxes out but only wrote about 8. Who is the ninth bridesmaid?

  6. So heartwarming to see the love you have for your friends! I just love everything you put in the box. I especially love that you picked two matrons of honor. I wondered how you’d choose between Tori and Sam…

  7. Why am I crying lol?!? Very sweet way to ask and honour your friends. I appreciate you sharing this beautiful and happy video. It brightened my day. Congratulations everyone.

  8. So thoughtful
    So touching
    I cried…still crying
    YOU are an incredible human being, friend, role model, mother and fiance
    YOU are also my FAVORITE person to follow
    Thanks so much for inviting us into your home and family/personal life
    I am also so grateful to have been able to purchase the FALL Box
    Forever one of your biggest fans – and now my daughter is moving to Kelowna! Not because of you but I would…if I didn’t have a husband!!! But I adore Bruce so I’m staying here in Ancaster, Ontario LOL

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