How to Pop the Question: "Will You Be My Bridesmaid?"

Bridesmaids, Real Weddings
Guest Blogger Ilana Stern With Her Bridesmaid

Photo: Courtesy of Ilana Stern

What do real brides have to say about the wedding planning experience? Well, it's not all happy tears at the bridal boutique and indulgent cake tastings. Over the next two months, guest blogger and Weddington Way founder and CEO Ilana Stern will share the ins and outs of planning a California wedding, running a business, picking the perfect wedding planner, and customizing your dress.

Unlike some of the other decisions involving the wedding (Should I get a wedding planner? Where should I have the wedding?), when it was time to figure out my bridal party, I knew exactly which girlfriends I wanted to be my bridesmaids. I also knew that I wanted to do something special, fun, and true to our friendships to ask them to participate in my wedding. Since so much dishing between my girls and I has happened over a glass of wine, I thought it was only appropriate to incorporate a bottle (or several) into how I asked my ladies to be my bridesmaids.

Champagne was a natural choice—I loved the idea of 'popping' the will you be my bridesmaid question with some bubbly. My bridesmaids are scattered across the world (several are in New York, another is in Peru, and a third is in Dubai!), so presenting them with champagne was a fun way for me to bring a celebration to them no matter where they were.

Instead of simply gifting the girls with a bottle of bubbly, I decided to have custom labels printed. Each label said: "Dear (insert maid's name here), will you be my bridesmaid? Love Ilana." Jenna Raberman of The Pink Lantern created the lovely labels to my liking. The next step was the fun part: Giving my friends the bottles! It was easy with the girls who lived in my hometown of San Francisco—I delivered the bottles in person. It was great to be able to exchange a hug and enjoy the champagne together afterward. I also went to New York City for work and was able to personally present the custom bottles to my ladies there. What a treat to see their smiles when I surprised them with the champagne. And how fun to celebrate by pouring some glasses!

Guest Blogger Ilana Stern With Her Bridesmaid

Photo: Courtesy of Ilana Stern

Popping the question to Astrid, one of my best girlfriends from college who lives in Dubai, and Dani, who lives in Peru, was a little more challenging. Since you can't ship alcohol internationally, I had to enlist some helpers to deliver the bottles. I conspired with Astrid's fiancé and Dani's mom and sent them the champagne label and a card. They affixed the label to a bottle of champagne and presented it to my future maids. Getting the others involved ended up making the delivery of these gifts even more special.

Guest Blogger Ilana Stern's Bridesmaid Champagne Bottles

Photo: Courtesy of Ilana Stern

Some of the girls who I didn't ask in person posted pictures of their bottles on Facebook with some crazy form of a "yes" response (as hilariously pictured, below). Seeing their creative and funny replies was a surprise for me, not to mention a glimpse of what's to come.

Guest Blogger Ilana Stern's Bridesmaid Creative Response

Photo: Courtesy of Ilana Stern

It reminded me that you don't really have to do anything fancy to 'pop' the question to your bridesmaids. It's simply a wonderful opportunity to let them know in your own way how much their friendship means to you. They are about to commit a lot of time over the coming months to making you, the bride, feel incredibly special and loved, so it's a a great chance before the craziness begins to return the favor and let them know how much you love them!

—Ilana Stern

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