How to Propose to Your Wedding Party in Westchester

Local couples are proposing to their wedding parties, and you can too.

Growing up, we often dream of that moment when our beloved drops to one knee. But couples today are doing more than just asking each other. Once the ring has been accepted, it’s time for brides-to-be to do their own proposing. This time, asking their maids of honor, bridesmaids, even flower girls and officiants, to join their wedding parties.

Many are getting crafty and creative in finding ways to pop the question, putting together proposal boxes with custom goodies or finding local companies to help make their ask, like a colorful balloon bouquet from The Westchester Balloon Company in Peekskill. Such websites as Pinterest and Etsy have pages of ideas devoted to items perfect for requesting members of your wedding party to join you as you take your vows. Just check out #bridesmaidproposal on Instagram and its more than 200,000 posts showcasing brides’ resourcefulness and ideas, including using cute sayings like “I can’t say ‘I Do’ without you,” and “I found my mister; now I need my sister.”

Adobe Stock/ Gartmanart

Not to be outdone, grooms are getting in on the act, too, sending the guys who will stand up for them custom cigars, booze, and monogrammed can Koozies.

- Advertisement -

Wedding party proposals are a growing trend, according to Melisa Imberman, owner of The Event of a Lifetime, Inc., in Chappaqua, who says it’s all about personalization of weddings and the desire to create an Instagrammable moment.

“Many of these proposals end up on Instagram, Snapchat, and TikTok, so the items are carefully curated to optimize the post,” she says. It’s a great way “to get your friends and family excited for the wedding and show them your appreciation. The possibilities are endless.”

“Weddings can be one of the most cherished occasions in our lives, and you’re asking your besties to come along for the ride,” says Sarah Banks of Foster Supply Hospitality, a group of independent hotels and restaurants in the Catskill Mountains that often host weddings. “What better way to say, ‘Please take this journey with me,’ than with a sweet and fun proposal? Giving these moments a special touch only enhances the memories that stick with us forever.”

Ready to pop the question?

These seven local businesses can help you propose to your crew:

1 | The perfect way to pop the question is with fun, flavored popcorn. Bri Marie Gourmet Popcorn of Blauvelt will create bags or boxes of gourmet popcorn for this special ask and even match it to your wedding colors. Include Cupid’s Crunch (pink, candy-coated popcorn with marshmallows, red, white, and pink M&Ms, drizzled with white chocolate), Wedding Wishes (crunchy vanilla popcorn with rainbow sprinkles), or Celebration Puffs (caramel corn puffs). Or create your own flavor combination.

- Partner Content -
gift basket
Courtesy of brand

2 | Just so you don’t think it’s only about food, consider proposing with a piece of jewelry from Tatiana M Designs of Briarcliff Manor. Design a necklace, bracelet, or ring that can be worn at the wedding and then cherished forever as a symbol of your friendship and a reminder of the day. Incorporate a gemstone that inspires love and joy or match it to your wedding palette.

Courtesy of brand

3 | A proposal in chocolate form has a 100% success rate. Ask members of your wedding party to join you with chocolates molded in any of thousands of shapes, including a high-heel shoe, diamond ring, or rose, with Chocolations in Mamaroneck. Or send a whole box of truffles spelling out your question.

Courtesy of brand

4 | How can you go wrong with something sweet? The Poppery of Mount Kisco will put together some “edible couture.” Choose from dozens of types of deliciousness, including Nutella hearts, cake pops, and blueberry macarons that spell out your message: “Will you be my something blue?”

Courtesy of brand

5 | Individualize your asks with delicious handcrafted and decorated cookies from the Ethereal Baker in Pleasantville. Get them in the shape of a diamond ring, wedding dress, flowers, or come up with your own idea, to say: “I’m such a lucky bride to have you by my side.”

Courtesy of brand

6 | Chappaqua’s The Event of a Lifetime will work with vendors like Bridesmaid Gifts Boutique (pictured) to create a customized box with a personalized card and all sorts of goodies, including candles, mugs, makeup, champagne, and chocolates for you to make your ask. “I try to customize each package to reflect the bride and her bridesmaids,” says Melisa Imberman. It could include something that has to do with the city where the wedding will be taking place, a hobby/interest of the bride, or how they met.” Make sure your proposal box includes something your “I do crew” can wear while getting ready on the big day, she says. “Bridal parties wearing cute matching items are Instagram gold.”

- Advertisement -
gift box
Courtesy of brand

7 | Get the groomsmen in on the ask with Small Fry Press. The Pleasantville company will customize almost anything you can imagine. Most popular with the guys are engraved flasks, shot glasses, keyrings, and dopp kits. Have them add a card with the all-important question: “Suit up! Will you be my groomsman?”

Gift set
Courtesy of brand

Related: 5 Easy-to-Maintain Plants to Add Serenity to Your Workspace

Our Westchester Home Design Awards event is June 26!

Our Wine & Food Festival returns June 4-9!

Our Wunderkinds event takes place on May 23!

Our Best of Business Ballot is open through May 15!

Our Healthcare Heroes Awards event takes place on May 9!

Our Westchester Home Builders Awards take place on April 4!

Our Diversity, Equity & Inclusion Forum is March 14!

Unveiled: A Boutique Bridal Brunch is February 25!

Our Best of Westchester Elimination Ballot is open through March 6!

Holiday flash sale ... subscribe and save 50%

Limited time offer. New subscribers only.