Top 10 Winter Bridesmaid Proposal Ideas

There are endless bridesmaid proposal gift ideas out there, but asking your closest friends and family to be in your bridal party isn’t about monogramed cups and personalized t-shirts. It’s about the experience of saying I do with the full support of your bridesmaids.

Make popping the question to your bridesmaids part of the experience by planning a proposal they will never forget during the winter season.

Here are our top 10 winter bridesmaid proposal ideas.

Two Women in Robes Toasting the Camera With Champagne Glasses: Ria Michelle

Sign Up for an Afternoon of Skin Nourishing Spa Treatments

The cold air of winter can leave your skin looking and feeling dehydrated. Why not treat your girls to an afternoon of skin-nourishing spa treatments so that they glow from the inside out?

Spend a day getting hydrating facials, body scrubs, and hair conditioning treatments. Pour a little champagne and ask your crew to be there for you on your wedding day when you’re lounging in your robes waiting for the next treatment.

Group of Women Taking a Sleigh Ride: Only in Your State

Take a Sleigh Ride

A sleigh ride is the perfect winter activity if you want to plan a bridesmaid proposal for just one or a few of your closest girlfriends.

If you work with the coachman, they may let you hang a sign on the side of the sleigh that says, “Will you be my bridesmaid?” You could also post a sign somewhere along your route and point it out as you pass by.

Three Women Posing For a Picture on Ice Skates: Strawberry Chic Blog

Go Ice Skating

Ice skating is another fun winter bridesmaid proposal idea. There’s sure to be plenty of laughs as you all try and skate some laps around the rink!

If you’re skating indoors, you may be able to get the staff to scroll a message on the jumbotron. Otherwise, it’s perfectly fine to ask your girls to be in your bridal party when you take a break from the ice to eat a soft pretzel or drink a beer.

Three Women Sitting in the Snow on a Sled: Pexels

Go Sledding

Bundle up and do some sledding when you ask them to be there for you on your wedding day!

Before the rest of your girls get there, write a message in the snow using a stick or food coloring asking them to be your bridesmaids. They will definitely be surprised when they sled to the bottom of the hill and see your message!

Person Holding a Christmas Gift: Unsplash

Pop the Question With a Christmas Gift

Christmas is the perfect cover for giving your future bridesmaids a gift and asking them to be in your bridal party at the same time. All it takes is a bridesmaid proposal box. With the message clearly printed on the top, you can put any gift you want inside, then wrap it with wrapping paper. They will be truly surprised when the message is revealed!

Group of People Standing Around a Table Laughing and Baking: King Arthur Baking

Take a Holiday Baking Class

Taking a class can be a fun way to spend time together when you want to propose to your bridesmaids. During the holiday season, it can be especially fun to take a holiday baking class.

You can take a class in person, but you can also take a class online. Invite the girls over, sip on some wine, and make something delicious in your own kitchen!

Take a class on how to make cookies or cakes and you can write, “Will you be my bridesmaids?” in icing.

Two Cups of Hot Chocolate With Whipped Cream and Marshmallows: Neilson Dairy

Ask Over Hot Cocoa

If you’re looking for a more relaxed, informal way to ask your bridesmaids, you can ask over hot cocoa. Invite them over to your house or hit up a coffee shop for a fancy hot chocolate. You can make the experience extra special by serving their hot cocoa inside a personalized bridesmaid mug.

Women Dancing at a New Year’s Eve Party at Home: May the Ray

Throw a New Year’s Eve Party

New Year’s is a great time to ask your girlfriends to become your bridesmaids. You can go to a party together, or you can throw a special party just for your squad. There are a lot of great theme ideas for an at-home New Year’s party!

If you want to make your bridesmaid proposal extra memorable, shout “Will you be my bridesmaids?” when the countdown to midnight is complete.

Three Women Dressed Up for a Murder Mystery Party: Chris Loves Julia

Host a Murder Mystery

Although you can host a murder mystery party any time of the year, it’s an especially good idea in the winter when you’re stuck inside.

Any old murder mystery will do, but you can take your bridesmaid proposal to a whole other level by creating a custom game just to ask your bridesmaids to be there for you on your big day.

Indoor Movie Fort With Pillows and a Popcorn Machine: Kara’s Party Ideas

Host a Movie Night

Another great indoor bridal proposal idea involves hosting a movie night. Make the living room extra cozy by covering the floor with pillows, filling bowls with snacks, and hanging string lights from the ceiling.

You can watch holiday movies, the latest release, or any movies you want. Squeeze Bridesmaids into the lineup and your girls will get the hint!

Winter bridesmaid proposal ideas don't have to involve extravagant or personalized gifts that have been wildly overdone. Choose an idea from this list and you can share a meaningful experience that’s all about your bridal party—before wedding planning becomes all about you.