Bridesmaid Proposal Box Ideas

I’ve been planning my wedding since middle school. I remember peaking out of the laundry room (where our computer was stationed growing up) and shouting to my mother, “hey mom, should Aunt Jenny be invited to my wedding?” My mother answered the question without thinking anything weird was happening and went on with her daily life.

I’ve had an account on The Knot since the summer I spent watching Lifetime from 9am to 12pm everyday. (There were a lot of commercials for The Knot.) I’ve envisioned a million different versions of this wedding - from Phantom of the Opera entrance dances to only serving soup (but like - 20 kinds of soup) to having a Second Line where a brass band leads you around the French Quarter in New Orleans to hiring a brass band to play Go the Distance as I walk down the aisle at a wedding where everyone is dressed up like Disney characters. And I have been keeping a mental (and sometimes not mental) list of who I thought would stand by me on my big day.

Since those days (over 20 years ago), some loved ones are no longer with us, I surpassed my Knot.com expected wedding date at least five times, I realized I didn’t have the budget for a full Phantom orchestra, and the list of friends I see and talk to on the day-to-day has continued to evolve. So when I sat down to plan my wedding in 2020, even though I had been planning the wedding for over two decades, it almost felt like I was starting from scratch.

Two folks on my bridal party list were obvious - my sister and my fiancé’s sister. It’s important to me to have those two by my side and for them to meet the other important people in my world. And then after much consideration, I realized I was overcomplicating it (much like I do with everything else in my life). The list of folks I chose was the list of people that I’ve called and reached out to at my worst in my adulthood. The ones who have seen me through tears, panic attacks, melt downs, and more. I don’t fully understand yet how people become those people in your life, but I’m very grateful to have them.

So now I had my list of people. What was I going to do with that? Especially in the middle of a pandemic.

Why I Decided on a Bridesmaid Proposal Box

I decided that I wanted to make a box of 6 items (one inspired by each bridesmaid) and to include a lot of photos of my time with that particular bridesmaid. By keeping each item in the $3 to $10 range, I was able to keep the overall process fun and reasonable. And creating this box did a few things -

  1. It created a really fun gift to open.

  2. It became a built-in icebreaker to introduce people to each other.

  3. It connected everyone in a unique way to make them part of the same thing right from the start.

  4. It helped them to see what they had in common.

  5. It allowed me to have the fun evening of going through all of my old photos to find my favorite ones.

  6. It served as a vehicle for me to ask them to be my bridesmaids.

The Items I Selected for The Bridesmaid Proposal Box

I tried to come up with items that were memorable, small, not breakable, light weight, reasonably priced, and practical for everyday use. I ended up choosing. Without incriminating anybody, here were the items that I chose -

  • A tiny bud vase for the friend who loves flowers.

  • A lottery ticket for the friend who played the Powerball with me when it got REALLY high.

  • Tea from Old Wisdom Wellness for the friend who loves tea.

  • A box of brownie mix made by Baked, my favorite bakery in NYC, for the friend with whom I would always visit the bakery.

  • Cuticle cream for the friend who helped me with my nails before prom.

  • Massage oil for the friend who pole dances.

I made sure to write on everybody’s card that there was an item in there that reminded me of each person and they should try to guess which item was theirs.

Maybe these items wouldn’t work for your bridesmaids. If that’s the case, here are a few questions you can ask yourself to help select an item:

  • Do they have a favorite color?

  • How does this person like to spend their time?

  • What are some of your favorite memories with them?

  • How do you spend your time together?

  • What are their favorite foods?

And then when all else fails, I recommend scrolling back through your photos together and messages you’ve sent each other to see if you get any good ideas!

Packaging the Bridesmaid Proposal Boxes

I actually tried to decide on the box size before choosing the items to go inside it so I could be sure that they fit. I even went so far as to call the bakery who made the brownie mix to ask them if they could measure the box for me before I purchased it. I was so excited when they did!

That said, the small flat rate box from USPS is really small (8-5/8″ x 5-3/8″ x 1-5/8″) and there are two medium box options, but both were a little too big in weird directions (11″ x 8-1/2″ x 5-1/2″ and 13-5/8″ x 11-7/8″ x 3-3/8″), so neither one of those ended up working out.

I kept thinking that I had to ship all of these items because none of my bridesmaids actually lived in my city, but I realized that even if they didn’t live in my city, I still saw some of them in real life. All of those were packaged in bags. At the end of the day, I only ended up mailing three out of six of them - one to Austin, TX, one to Brooklyn, NY, and one to Richmond, VA. I found random boxes, UPS-ed them, and spent a total of $50.98 on shipping. Shipping to Brooklyn and Richmond was only about $11. Shipping to Austin was about $24. I tried pricing it out on USPS and the prices were so close that it felt worth it to pay for the faster shipping from UPS.

The Overall Price of Bridesmaid Proposal Boxes

The total price came to about $325, including the shipping, or about $54 per box. The most expensive item in each box was the massage oil ($13/item), followed closely behind by the brownie mix ($10/item). This amount was within my budget and I was so glad about how the packages turned out.

If you were looking to do it for cheaper, I think there are some adjustments that could be made -

  1. Shop local to avoid shipping (pandemic times were weird…)

  2. Find mini versions of items

  3. Choose only one or two items on which to splurge

How Bridesmaid Proposal Boxes Were Received

People seemed to like them! During our first meet-up together, it was a great topic of conversation. Everyone tried to guess which item in the box was placed in it because of them, and then got to know everyone else a little bit better based on which item was chosen for them.

I would absolutely do this again. It even made me want to send out random packages to people throughout the year. Who knows, maybe that’s something I’m going to have to start doing…

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