Editor Brittany Jasnoff tackles your toughest big-day conundrums.

Illustrations by Lan Truong

Most of my guests are flying in from out of town. How much entertainment—and transportation—do I need to provide for them?

These days, weddings aren’t just one-day affairs—they’re entire weekends filled with Friday-night welcome bonfires, Sunday-morning farewell brunches, and, of course, your big, important moment in between. How many amenities you choose to offer your friends and family is entirely up to you, although hiring a bus or trolley service to transport them from hotel to ceremony to reception would certainly be a nice touch. Many couples also include a list of favorite activities and restaurants on their wedding website to help guests make the most of their mini vacation, even if time or money won’t allow for formal pre- or postwedding celebrations.

I’ve decided to plan my wedding without any outside help. Should I listen to my maid of honor and at least hire a day-of coordinator?

Picture yourself, if you will, on your wedding day. The photographer is ready for portraits and you’re still in hair and makeup. Meanwhile, the DJ, florist, and linen company need to coordinate setup. And that’s all before you have to corral the rowdy bridal party for the processional and cue the harpist. Do you really want to be the one to handle these logistics on what’s supposed to be the most important—and enjoyable—day of your life? I didn’t think so. Even the most organized brides in the world need someone to put out fires before, during, and after “I do.” In some cases, you can rely on your hotel’s catering manager to do the heavy lifting, but if you’re getting married in a barn, on the beach, or any other venue without an on-site coordinator, you should absolutely hire someone to execute your dream the way you imagined it. It’ll be worth every penny, and then some.

I work in a small office with just eight other employees. Many have already asked for details about the wedding, and I’m worried that they assume they are all invited. Is there any way I can covertly invite two colleagues I view as mentors?

Office politics are tough to navigate on any day; throw a wedding into the mix, and things get even trickier! Normally, there’s nothing wrong with cherry-picking a few of your favorite colleagues and supervisors. But you’re right to assume that with a team that small, it’s highly likely the few people you didn’t invite will find out—and that could cause hurt feelings. If you can’t have them all, it may be wisest to keep everyone off the list, and chalk it up to that pesky little monster called the budget.

I thought I was done with proposals when my fiancé popped the question—now I’m hearing about the “bridesmaid proposal.” What is that, exactly, and should I consider doing one?

This is really just a fancy name for what brides have already been doing for generations: asking their best friends to play a supporting role in this most special of days. With the advent of social media, however, people have started to get a lot more creative. But there’s no need to break out the flash mob for your girls. Thoughtful gestures tend to work best—a package filled with ’maid must-haves (don’t skimp on the bubbly), a cheeky and/or sappy card, or a Ring Pop in lieu of a diamond should do the trick.

My mom wants to wear black to my wedding, but I’m afraid it’ll look like she’s in mourning. How much of a fuss should I make about this?

The LBD is a smart, sophisticated choice for many occasions—including, yes, funerals. But cut your mom some slack: Some women just don’t feel comfortable in gold lace or blush taffeta, even on their daughter’s wedding day. If your event is a formal evening affair, in particular, a long black gown is more than appropriate—especially if it’s gussied up with some extra-special mother-of-the-bride details (beading, embroidery, 3-D florals). If it’s an afternoon wedding on the Vineyard, perhaps you could gently steer Mom toward another neutral—may I recommend taupe?

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