Twice a bridesmaid, always a wedding planner. Kaitlin Everett, owner of Everett Events in Richmond, is not only steeped in weddings professionally, she’s also served as the maid of honor for both of her sisters. So, who better to ask how to have a drama-free wedding party experience?
The life of a bridesmaid often gets a bad rap—lavish trips, expensive dresses, and more themed showers than one thought possible. But it doesn’t have to be that way. The key is for both parties to set expectations from day one. On one hand, the bride likely has a vision. But, on the other, the wedding party may have financial constraints and responsibilities that prevent them from jetting to Cabo for a five-day bachelorette party.
Everett recommends open lines of communication and a focus on the traditional duties that won’t drain your savings account, including helping the bride chip away at her long to-do list and interfacing with vendors or prying relatives while she’s trying to get her hair done in peace. “First and foremost, your role is to be a support system for your bride. That doesn’t require any money!”
But anyone who’s walked down the aisle in a matching dress knows that most weddings go beyond day-of duties. Everett explains that the wedding party often pitches in to organize some of the major events leading up to the big day, especially the bachelorette party. The maid of honor typically takes the lead—from researching an activity or deciding on a dinner reservation.
When it comes to the bridal shower, Everett notes that bridesmaids are often asked to step in with a secondary role, which could be lower-stakes items, such as games or décor.
“Being a bridesmaid is not only an investment monetarily, but it’s also an investment of time,” says Everett. However, most importantly, she adds that there’s one more investment to keep top of mind. “This is an investment in your relationship with that person.”
All photos by Kaitlin Everett. This article originally appeared in the February 2026 issue.
