How I Chose My Bridesmaids & Groomsmen

Selecting your bridesmaids & groomsmen begins with consideration and empathy.

Since we were doing a smaller destination wedding, the bridal party thing wasn’t clear to either of us. While I haven’t been in anyone’s wedding before, my husband had, along with a bunch of our friends. I’ve heard plenty of stories about too much money being spent, poor organizational efforts, and lots of drama.

We knew we were asking a lot of people. Destination wedding = Please buy a plane ticket, a dress/suit, plan events, pay for some of that event, and then tolerate our inevitably exploding stress levels.

Immediate guilt came over me.

But unlike my only-child-self, my husband has a younger brother who technically should be Insta-Best-Man. And then there was that time where I told my best friend of 15 years, very drunkenly, “If I ever get married… you’re gonna have to be my Bridesman… my Man of Honor!”

But how do I pick and who do I choose? Can’t I just have none?

We were circling around this subject one night after dinner, and I could hear in my husband’s voice that he really wanted to have people by his side.

“I have to have my brother… I would love to have Aaron, and then there’s Jenn.”

“That’s actually brilliant — if you have Jenn than I can have Justin… we can each have our opposite-sex-friends by our side!”

A moment of uniqueness slightly shrouded in tradition = YES.

* * *

After further thought on my part, I realized how much of an ass I would be if I didn’t ask Mandy, the infamous Ivory Aisles Fashionista, to take an official part. She had been instrumental as the local voice of reason while ensuring individuality was achieved at all levels.

*Queue technological science fiction voice*

Bridesmaids now 66% complete.

* * *

Who do you want in that room, helping you fend off bridezillaness, batting mascara from those love-laden eyes, or seeing you nearly naked because they have and, in this moment, has to?

When sussing out Maid of Honor material, in family or in friendship, ask yourself the question above. My guess is you’ll know who fits that description immediately. Yes, it is a bit trite (there is far more behind your reasons and your kinship), but guttural reactions to simple questions often lead to truth. Trust your gut on this one.

I imagined myself spending the day in a room with my favorite ladies (Jenn included) and had a moment of pause. I thought I could do this whole wedding day thing alone because I’m told I have superhero powers when it comes to getting shit done. But let’s get real here. I’ve never done this before, so why the hell would I ever think I could just make it happen without asking for help? I needed someone that I was more comfortable with than my own mother (sorry mom!). Someone I could ask to do anything, be there in any way I needed, and steer me away from Bridezillaville.


When you’ve been friends since college, you’ve been through it all. Carla is the trusted friend who offers objective advice, free from judgement, and gives with the mightiest of hearts.

She also had the right resume for the job: Active bridal party member for scores of weddings in the past, been through the bride thing first hand, and as a fellow art student, the match was made!


One thing they never tell you about is the secret honor society of friends, old and new. We had moved to Beantown two years ago, and the problem I ran into was not just which of my friends to choose, but which of the newly made friends here in Boston versus the old friends from Connecticut.

The day after calling Carla to ask if she’d be up to the task of Matron of Honor, I went out for a mani-pedi with my two Boston besties (non-bridal-party people). Our engagement shoot was later that week. I shared this factoid with the delicate Vietnamese lady working on my hands.

“Oh oh, these your bridesmaid?”


“…no… but these are two of my closest and newest friends… who I wish could be in the bridal party but we just…” I rambled on and on and felt terrible.

This was intensely awkward.

None of the wedding sites told me to look out for uncomfortable circumstances brought on by kind intentions!!!

I looked at Skye and Kim with an apologetic harumph on my face.

Even though they’re amazing, non-caddy women, I was speechless and couldn’t talk about it until another week went by.

Yet in truth, the day we arrived at the nail salon, I had known Skye and Kim for all of 4 months. It is silly to be so upset, but great friends are like finding your husband — when you know, you just KNOW! They may not trump your oldest friends, but they still matter, dammit.

* * *

Back in wedded-to-be land, things were going smoothly for the bridesmaids. All three women are incredible organizers, get-shit-done-rs, and forthright about their experience or lack there of, which made for a bridal party dream team. Here’s the breakdown:

Role & Responsibility: Primary voice of reason (first call for all things), next of kin creative, chief bachelorette officer.
Tasks: Reminding me and asking me, “Yes but what do YOU want honey? This is your day.” Also spearheading initial communication, sussing out fabric colors for dresses, test driving paper flowers from afar, gut checking vendor choices, and taking on the handmade task of creating an interactive guestbook.

Role & Responsibility: Host and organizer of the anti bridal shower (more on this later), VP of bachelorette operations, fellow crafter, groom’s bestie (and thus receiver of special title).
Tasks: Secondary voice of reason regarding planning and destination-like goodness, captain of people gathering, bridesmaid dress tester and reporter, access to day-of runners, and supplier of paper flower power.

Role & Responsibility: Adviser and assistant to all, fashion maven, skincare and makeup monarch, bringer of 100% sass.
Tasks: Communications keeper, supplier of paper flower power (article about this coming soon), wedding dress + jewelery judge, cracking the whip of hydration for added skincare benefits on the day of.

Meanwhile, in groomsmen land…

Things were… going as expected. The Insta-Best-Man brother had recently been dumped for the second time in the last year. Blinded by a broken heart, he focused on how events could benefit him rather than the groom. The best man in proxy begrudgingly tapped into his dazzling planning agility, which made it feel like work rather than pure fun. And, my “man of distinction” / best friend had a crazy schedule and doesn’t do email very much (as it turns out, neither does my brother-in-law).

This was a little exhausting. Not gonna lie.

We picked the most meaningful people to be in those groomsmen seats, and we knew what we were getting into. Your lesson here is to just embrace it. Accept who your favorite people are, as individuals and what they might be like as a group. Perhaps run a pre-mortem to imagine what the pitfalls and successes of such a group might be to better prepare yourself. But, regardless of the outcome, family is family, no matter how you cut it.

So what happened next? After all the celebratory preludes and their associated libations, THE BIG DAY arrived. I can’t truly articulate how grateful I am for all the effort, support, and love we felt from each member of our bridal party, but I’ll tell you this much — it was one hell of a party!

In Conclusion, Choose Your Bridesmaids & Groomsmen with this in mind:

  1. Honor yourself by acknowledging those who are the most meaningful to you — regardless of gender, relationship, or organizational capacity.
  2. But while you’re honoring them, be sure to accept them for exactly who they are — no bridezilla overzealous expectations aloud!
  3. Be 100% yourself. Ask for precisely what you want or don’t want. Start there, then, be willing to bend with the wind and adapt to the restraints around you. Limitations will always breed creativity.
Bridesmaids & Groomsmen
Photo by Sandra Costello ( )

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