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How To Pop The Question To Your Bridal Party

By Rebecca Padgett Frett

The most important question has been asked and answered. Now it’s time for the leading man and lady to pop a question to their supporting cast. Below are a timeline, tips and ideas for securing your bridal party.

Select your Squad

When you picture your wedding day, who is standing by your side? They are the people who should have a spot in your bridal party. Consider your relationship with these significant players knowing that throughout the planning process and during the wedding weekend, they should provide comfort, fun, joy and most importantly, support. You’ll want to select your maid of honor and best man, and yes, you can have multiples. Your bridal parties can be unbalanced on either side of the aisle.

Photo by Woodland Fields Photography

When to Ask

As excited as you may be, wait until you have a date and venue set before asking people to be part of your ceremony. These are two very important considerations that the members of your intended bridal party will likely want to know about before committing. Once they are established, feel free to ask. It is best to make the ask at least eight months to a year in advance, allowing the bridal party plenty of time to make travel arrangements and add costs to their budgets.

How To Ask

This is dependent on a variety of factors: your proximity to your bridal party, whether you want to spend money and even your personality.

If you all live within reasonable travel distance of one another, it can be fun to invite the group to a gathering and let them know on arrival that they are participating in their first event as a bridal party. Consider a game night, brunch, wine or beer tasting, dinner, a spa day, golfing or any other activity you would enjoy doing together. For a more personalized experience, you might take individuals on friend dates and discuss your wedding.

Photo by Black and Hue Photography

If you’re all living in separate locales, the best option may be to send them a package in the mail. Many packages include items such as a framed photo of the two of you, drinkware (flasks, shot glasses, wine tumblers), clothing items, sunglasses, bowties, candles, jewelry, selfcare items, alcohol, food items and more. Sending a bouquet of flowers is also a thoughtful and unique idea. In sending your packages, include a letter or a card that asks, “Will you be my bridesmaid?” or “Will you be my groomsman?”

If a package is out of your price range or simply not your style, do send a letter or card. The handwritten sentiment is made all the more special if you express why you selected the person to stand by your side.

Lastly, there’s always the option to just ask. If you do decide on this option, do not ask via text or email. Arrange to meet in person, on Facetime or via a meeting platform such as Zoom.

Photo by Sarah & Paul Photography

Have a Follow Up Conversation

If you send a package, be sure to get a tracking number. If the package arrives, but the person hasn’t responded within a reasonable timeframe, check in with them. More than likely, they will respond with an enthusiastic “Yes!” Each member of the bridal party should be informed of your expectations, estimated costs and event dates. Do remember that they can say no. This usually is not reflective of their relationship to you. Likely it stems from financial stress or scheduling conflicts.

Make Introductions

Once all are on board, it’s time to meet one another, if you’re not already all acquainted.  Again, if you’re all local, arrange a casual meet-up. Meet-and-greets can otherwise be conducted via a text group, email chain or social media page.

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