What I’ve Learned As A Professional Bridesmaid

Over the last 365 days, I’ve helped out over 30 brides. I’ve fluffed more veils than I can count on one hand, and danced both the Horah and The Electric Slide more times than I’d like to admit. No, I’m not the most popular woman on the East Side of Manhattan. I’m a professional bridesmaid, and I’ve helped dozens of strangers have the best days of their lives. A few years ago, when all of my friends started getting engaged, I started making new, single friends. Friends who wouldn’t mind piggybacking onto a Friday night of bar-hopping or a Sunday afternoon of endless chatting over scrambled eggs and avocado toast. Friends who didn’t ask me why I was still single more often than they asked me how I was doing. There was nothing wrong with my newly married or freshly engaged friends: They just had to-do lists that looked foreign to me. Their weekend plans included going shopping for the week at Whole Foods with their S.O.'s, while mine included binge-watching Orange Is the New Black on Netflix or mapping out the dance floors on the Lower East Side I wanted to take over on Saturday night. They no longer called me with adventurous plans to book backpacking trips to Costa Rica; instead they were more interested in saving money for things like mortgages or their baby’s daycare bills. Soon, though, these new, single friends of mine started showing up at brunch with twinkling diamond engagement rings and fairy-tale stories of how he’d popped the question while she was collecting shells on their trip to Tulum. I’d sit there and listen while nervously devouring blueberry muffin crumbs; I knew the question that was coming. I had already been asked — by women ranging from my current BFF to someone I hadn’t been close with since our junior year of college — once, twice, no five times before: “Will you be my bridesmaid?” During the time when all these bridesmaid invitations were coming my way, I was a lot of things: a full-time copywriter, a struggling blogger, the kind of girl who couldn’t make it past date number one without having an anxiety attack. Dating was not on my list of successes. But now, to add to that list, I was a perpetual bridesmaid — and I was good at it. Suddenly, it hit me: If weddings were going to be such a big part of my life, why not get paid for it? Why not become a professional bridesmaid?
So one night, I found myself canoodling with my emergency stash of vanilla-bean ice cream and opening up my geriatric MacBook to a website that people usually turn to for old couches, new jobs, and even missed attempts at love: Craigslist. I told complete strangers that I’d be there for them, whether it was to be the personal assistant or peacekeeper during their wedding, or just listen to them chat about their challenges months before the big day. I wrote the ad before the ice cream melted and pressed send. Five days and 459 emails later, I started working with my very first bride, Ashley. After 37 phone calls with her over the course of two months, I found myself sitting nervously on the runway of the Minneapolis–Saint Paul International Airport, ready to take part in Ashley’s wedding. This was the first time I had ever been hired to be a bridesmaid. I had done it for my friends more than a handful of times, but here I was doing it for a complete stranger. Would her other bridesmaids take me in as their own, or would they reject me? Would I know how to help someone that I’d only known for 65 days? Ashley had replied to my Craigslist ad after firing her maid of honor, a good friend of hers who became not such a good friend after Ashley got engaged, ignoring her phone calls and making her feel bad about being over-the-moon excited to walk down the aisle. Though we often don’t expect it when signing up to help usher our friends through their wedding days, friendships can fall apart after the wedding is over — or sometimes even before. Despite my nervousness, Ashley's wedding went flawlessly. I was by her side for her first look, on the dance floor with her 'til midnight, and even a helpful hand when she needed someone to lift up the layers of her dress to pee.
Many more customers followed — and, to my surprise, some of them went from being customers to being close friends. After Ashley, I worked with Rod and Buck from Australia; Jen and Nancy from Chicago; Elle from Texas; and many others. Bryn from Brooklyn and I especially hit it off. As I left her wedding, I hugged her goodbye and said something I never thought I’d say when I started this business last year: “Can we still be friends?” I said it in an honest way, a way I hoped would put the exchange of money for temporary services in our past. I hoped the whole I-found-you-on-Craigslist thing wouldn't matter to my brides after they said "I do" — and I said "I do" to my next client. And it didn't, because many of them entered my life in a real way. We spent hours on the phone and days texting back and forth. Sometimes after a wedding, that kind of hectic back-and-forth stopped, and sometimes it didn’t — and I was glad. June 27 of this year marked one year since I had posted that first ad on Craigslist. There I was, eating my third slice of pizza of the night on Grand Street beside Bryn from Brooklyn — three months after her wedding. Despite her to-do list looking a bit different from mine, she’s always down for a leisurely meal. All your best friends were once strangers to you. Bryn was no different; I just met her a little differently than how most people meet their best friends. One year and 30 weddings later, I’m grateful that my business has brought me more than just financial compensation. It’s brought me the everlasting knowledge that friendships don’t have to end after you walk down the aisle. If there’s that spark — the one that goes off in your head that says, “This person gets me, me and my tiny little intricacies and the things that make me uniquely weird, and I totally get them” — then your friendship will outlast the leftover wedding cake you stuck in your freezer.

More from Sex & Relationships

R29 Original Series