Advice about Choosing Your Wedding Party for your Caribbean Destination Wedding

Good morning!

Well, I got my wish and it really rained on us last night!  Off and on, but we got up to check the windows to make sure it wasn’t raining in during the wee hours because it was raining so hard.  You can really hear the rain coming from one side of the house or the other with these metal ventana windows, and I’m always a bit paranoid.  It’s a holiday, but we’re working today.  Bill is over at the new office space with a crew installing new locks and ceiling fans, and I’m doing paperwork and catching up on client files.  Fun fun fun!  But before I jump into that mess, I thought I would write a quick blog entry about a topic I get asked about a lot — choosing the wedding party.

I get a lot of email from brides who aren’t my clients and aren’t getting married on Vieques or Culebra Island, asking me for advice on different matters for their destination weddings.  For the past two years, I’ve simply emailed them back with quick answers and wished them the best.  Occasionally, the topics have been interesting, so I’ve decided to start posting some of the most common questions here on the blog and answering them for everybody!

Dear Sandy,

I’m getting married in the Caribbean (but not on your island) and I was wondering if you could give me some advice about my wedding party.  I have six bridesmaids and Joe has a best man and five groomsmen.  I can’t seem to pick a maid of honor because I don’t want to hurt anybody’s feelings.  Is it really that important?  Do I have to single out one friend?  And how do I choose a bridesmaid dress when one friend wants short and strapless and the other wants long and formal?  One is a size 6 and the other is a size 16.  Help!

Amy G. in Dayton, Ohio

 Wow, Amy — you’ve got a lot going on with your wedding party.  I know the feeling — I had two Maids of Honor and four bridesmaids.  Actually, I had five bridesmaids but one got pregnant with a due date the same week as my wedding so it reduced the number by one.  And that was a good thing.

Is it important to choose a maid of honor?  Sort of.  Weak answer, I know.  But it’s the truth.  You need a MoH to be your right-hand girl during your destination wedding weekend.  She’s somebody who will help keep you on schedule, remember to bring the things you need to bring to each event (your lipstick, powder, the rings, for example), and who will run interference for you when your mom, his mom or one of your other girlfriends is driving you over the edge and you need some space.  Before you actually get down to the island for your wedding, the maid of honor is the one who spearheads all the important activities, like your bridal showers and your bachelorette party.  She’s not necessarily the hostess of these events, but she makes sure that somebody is handling each of them and that everything is under control in the big picture.

I couldn’t choose between two of my girlfriends for maid of honor.  My oldest girlfriend at the time lived on the opposite side of the country and had a small child.  She was in no position (financially or time-wise) to take on any additional responsibility for my wedding.  The two girls I was closest to in DC were polar opposites — but they got along okay and I decided they could work together.  One is a lot of fun but a complete organizational disaster, so I never would have trusted her with this on her own.  I love her and I’m close to her, but if she’d dropped the ball on anything, I would have had to kill her.  The other girlfriend would have killed me if she hadn’t been given the honor.  So appointing them both Co-MoH seemed a good idea at the time.  In the end, it probably wasn’t my best judgment call ever.  The detail-oriented girl did all the heavy lifting and hard work — she’s the one who helped me with all the un-fun preparation for the wedding (I handmade all my favors for both Vieques and the reception back in DC) and who hosted a shower and the bachelorette party.  One did all of the work, both got the glory, such that it was.  When I did extra special thank yous for my wedding party, those two got spa days and the others got gifts.  One had really earned it and the other had just been along for the ride, but I couldn’t be like that.  So then I felt bad for the one who had done all the work and I did something else special for her.  Again, it was all with the best intentions and it worked out, but it was stressful and I ended up spending a fortune.

It is a very good idea to choose one person to honor with the MoH title.  She’ll be the one who helps you stay centered and makes sure things go smoothly when you can’t be out front doing it yourself.  If you choose two girls, just make sure that you split up the duties and responsibilities equally so that nobody is stuck doing all of the work.  It makes for bitter friends.  And have an honest, straight-forward talk with them from the beginning.  Tell them you love them equally but you recognize that each of them has different interests and talents so you’ve tried to split things up to make it fun for everybody.  And always include both of them in the big adventures (dress shopping, tastings, invitation stuffing, etc.).

Choosing a good best man is just as, if not more, important than choosing your MoH.  Let’s face it — most of the time (and there are exceptions), the groom is the one who is a hot mess the afternoon of the wedding.  The best man’s job is to get his buddy showered, dressed and where he’s supposed to be when he’s supposed to be there.  He’s responsible for having a beer on hand for the groom but not allowing the groom to do shots.  He’s responsible for having the ring — and he’s responsible for having an extra copy of the groom’s vows (if you guys are reading them versus the minister).  He’s responsible for the first toast (preferably one that isn’t too inappropriate) and he’ll probably be the one to seat the moms at the ceremony.  But other than that, he’s just there in case the groom needs somebody to lean on.  Still, it’s important that you have somebody as best man that the groom isn’t going to have to babysit.  And if the groom has to ask his brother to be best man so that there isn’t a family drama, and the little brother has a tendency to get drunk and arrive late everywhere, make sure that another groomsman has been assigned to pick up the slack where the best man is dropping it.  Guys don’t care who is the best man.  Maybe some do, but my experience is that they really don’t give a hoot and probably, most of the time, wish they didn’t have to put on a monkey suit and stand up in front in the first place.  They’re doing it because someday they’re going to make their buddies do the same thing for them.  It has nothing to do with friendship and rank and favoritism, which is exactly what it’s all about for the girls.  Sorry ladies, but it’s completely true.  We’re petty.  And weddings seem to engender more pettiness than usual.

I’ve noticed that most of my wedding parties go one way or the other in size.  It’s very in vogue right now to simply have one attendant each — a MoH and a Best Man.  But there are still girls who ask all their bestest girlfriends from the past 30 years (I was one of those).  I’m not sure which one is better.  For me, as a wedding planner, smaller is better.  Because that way I’m not trying to get 16 people to stop chattering during the wedding rehearsal.  But for each bride, it’s different.  Sometimes I think that only one attendant means you miss out on the group thing with your bridesmaids.  I’ve had a lot of fun (as a bride and a bridesmaid) with groups of girls, getting our mani/pedis and our hair done the day of the wedding.  It’s a great way to reconnect with old friends you knew through each other and to build new friendships.  It’s a wonderful thing you can do for the girlfriend whose big day is coming.

But do keep in mind that your costs go up as the size of your wedding party grows.  Every client is different, but most brides and grooms get expensive thank you gifts for each member of the wedding party.  And sometimes, they even help subsidize the accommodations for certain members of the wedding party.  Brides may treat their girls to a beauty day the day of the wedding so that everybody looks their best for the pictures.  And every bouquet adds more to the flower budget.  Your wedding budget goes up incrementally with each person you add to your wedding party, from ring bearer to flower girl.

Sometimes we feel obligated to include somebody in our wedding party that we really, really don’t want to include.  Don’t do it.  Listen, some hurt feelings in the beginning (she’ll likely get over it in time to throw you a bridal shower so that you feel like crap for not making her a bridesmaid) are a lot better than you being miserable the week of your wedding because you have included somebody who is bossy or overbearing or who just grates on your nerves to spend the most important moments of your life right next to you.  You can always give her another job if she’s someone you love but just can’t stand to spend a lot of time with — she can pass out programs or hold the sand for a sand blending ceremony or do a reading and know that she’s important to you.

Having been a bridesmaid in somebody else’s wedding does not obligate you to ask her to be in your wedding.  Same goes for guys.  When my cousin got married with a humongous wedding party, somebody told me it was because he’d been in all these fraternity brothers’ weddings so he had to have them in his.  If the groom was a super-popular frat boy, he may well be in a lot more weddings than the number of  groomsmen that is appropriate for your wedding (think “27 Dresses”).  You can even ask a few guys to act as ushers rather than groomsmen, just make sure they’re clear on the difference and figure out what you want to do with them during pictures in advance.  We had a little awkwardness at my friend’s wedding when the usher joined the groomsmen up front at the ceremony because he didn’t know any better.  At that point, it’s too late.  The point is that you don’t have to have everybody in your wedding who asked you to be in theirs, especially if you’re having trouble keeping to a reasonable number.

As for the other part of Amy’s question — asking about bridesmaid dresses — that’s a whole new topic for my next blog entry.  You’ll have to come back later and learn about that!

And remember — if you have a question — just email me at and I’ll try to respond to you in a future blog entry.

Until next time, happy wedding planning from Weddings in Vieques and Weddings in Culebra!


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