Creative Ways to Propose to Your Bridesmaids

Gal pals are the best. You’ve found your soulmate in your fiance… but he/she is never going to be able to compete with your best friends. Your friends would do anything for you. If you’re having a bad day, they’d drive over at midnight in their pajamas, toting pints of icecream. They’ll be the ones offering you support as you navigate the many stresses of wedding planning.

There is nothing more powerful in the world than the bond of female friendship. Your BFFs will soon be spending a lot of time and resources making you feel like a queen. This is your opportunity to show your girls how much they mean to you. And to start getting EXCITED about sharing this adventure together.

Order A Pizza

Sounds simple right? This one actually takes a bit of logistical planning, so take notes. Shoot your friends a causal text asking if they’ll be home at 6 pm. Be coy. If they ask why (which they surely will) tell them you’re sending them a package and they’ll need to be home to sign for it. They’ll be excited, and a little suspicious, but will never see it coming. Then call a local pizza joint. Make it easy on yourself and just opt for somewhere like Dominoes or Papa John's. Somewhere you know, for certain, delivers to their house. Then call the pizza place to put in the order- don’t order online. Tell the person on the phone what you’re doing and when you’d like it to be delivered. Then ask them to write this message on the inside of the box:

“I know this is cheesy… but will you be my bridesmaid?”

This is one of my all-time favorite ways to propose to a bridesmaid.

Confession: That’s because this is what my sister-in-law did!

The stories from her bridesmaids are hilarious. Some of the pizza guys got really into it. One guy even got down on one knee and opened the pizza box and presented it to her as a true proposal.

Unknown to my sister, another of her bridesmaids was having a MAD craving for Dominoes all day. But she decided to be frugal and pick up a frozen pizza from the grocery store on her way home from work instead. She got home and was relaxing a bit while waiting to “receive her package”. She heard a knock on the door and was super confused when there was a Dominoes delivery guy at the door. She thought she had gone into a craving-induced blackout and ordered Dominoes AND picked up the frozen pizza. Once she saw the message, though, it all came together. Now it's a funny story for her wedding scrapbook.

Coffee Date

Tell your BFFs you’d like to treat them to a coffee date. Arrive a little bit earlier than planned. Bring a special mug with “Will you be my bridesmaid?” written on the inside on the bottom of the cup. Give the mug to the barista and tell them to put her drink in that mug when she arrives. Then, relax and enjoy yourself! When she finishes her coffee, she’ll have a surprise message written on the bottom.

Celebrity Message

Did you know you can hire celebrities to make a video message for you? Keep in mind, these aren’t celebrities like Brad Pitt or Leonardo Decaprio. But Cameo has a lot of recognizable celebs for hire! If your BFF is a big fan of the show Friends, you can hire Ross’s ex-wife Carol to make a video message for your friend. Are you a fan of The Office? If so, you can hire Kevin, Toby, Oscar, or Stanley. There are pages and pages of celebrities to choose from. This is a great option for a bride (or bridesmaid) who values minimalism. You want to do something special for them. But don’t necessarily want to waste money on more stuff, this is a super fun option. They’ll always be able to access and treasure these videos. Most celebrities on Cameo give the money they earn their favorite charity. So you can feel good about where you're putting your dollars.

Mini Succulent

If your friends are plant-lovers they’ll love this option. Plants are wonderfully symbolic of relationships. Just like a friendship, you need to nurture and care for your plant. If you do that, it’ll live forever and blossom beautifully. Send your best friend this wholesome message. Then, to lighten the mood, include a card that says, “My wedding would Succ without you”.

Indulge Their Sweet Tooth

This is basically the same concept as pizza delivery. But there are some crazy people out there who don't like pizza! And this option requires less logistics. Candies, cakes, and chocolates don't necessarily need to be served hot.

You can order a delivery of baked goods as well for the bridesmaid with a sweet tooth. You can even order from some of the top bakeries in the world. Here is a list of 10 NYC Bakeries that will deliver all over the country.

Send Her Flowers

Flowers don’t have to be romantic. Everyone loves flowers! Nothing makes a girl feel more special than enjoying an unexpected bouquet.

DIY Goodie Box

There are plenty of Etsy artists who will make a special label, put it on a bottle of wine, candle, or bath bomb. There are some stand-alone companies like Bottle Your Brand who provide this service too. These companies are a fantastic option. These artists do beautiful work. But they’re also usually super expensive. And to tell you a secret- the wine usually is pretty low-caliber. I prefer to get a little crafty. I’ll make my own labels on Canva and print them out at Office Max. Then I’ll buy a few bottles of wine at Aldi and a few Walmart candles and assemble the gift baskets myself. It’s a much more affordable way to pull off this method.

Rent out the Movie Theatre

Did you know that as of 2020, you can now rent out a private theatre viewing experience for $99 at Chattanooga AMCs? If you call the theatre ahead of time to arrange it you can also plan to screen a secret message. This is a great way to propose to all your bridesmaids at once (if they’re all local, of course).

Fortune Cookies

Use this website to order fortune cookies with a personalized fortune on the inside. Then invite your BFFs for sushi. Tell the waitress to give your fortune cookies at the end instead of their own. They’ll never see it coming.