Choose friends who understand you.
Think about the roles you’d like your bridesmaids to play—from supportive listener to party planner—advises Kate Chynoweth, author of The Bridesmaid Guide: Etiquette, Parties and Being Fabulous. Consider friends with whom you’re in touch regularly, who live close by and whom you’ve known to e dependable team players, since a lot of planning is consensus-based. And don’t be afraid to ask your best guy friend.
More isn’t merrier.
Chynoweth recommends having six or fewer bridesmaids unless you’re inviting 300-plus guests. Pare down your list of potential ’maids before you start extending invitations, so you don’t lose track and find yourself with a larger group than you’d like. While it’s appropriate to include your future sisters-in-law, inviting other in-laws and extended-family members is up to you. Don’t feel obligated to "repay" friends who asked you to be in their weddings if your relationships have since fizzled.
Timing is everything.
Enjoy two to four weeks without asking anyone to be a bridesmaid, NYC-based wedding planner and designer Michelle Rago advises: "It’s lovely to be engaged and focused on this huge life change." Try to choose your ’maids within the first three to five months—ideally, they should have six months’ notice—and ask everyone at about the same time so no one feels last.
Pop the question with style.
Ask each bridesmaid individually, not in a group, so they have the opportunity to say no if they so choose. "Remember, you’re asking her, not telling her," Rago says. Chynoweth suggests sending a note with a special photo or token of your friendship. Give a T-shirt or tank top that says "Bridesmaid" or, if you already know your wedding colors, send an accessory (like a necklace or headband) that matches. Take prospective bridesmaids who live nearby to meaningful locations like a favorite lunch spot, and invite long-distance pals over the phone, not e-mail.
Be up front with close friends you don’t invite to be bridesmaids.
"Always tell them in person so they don’t hear it secondhand," advises Chynoweth. Say, "As a couple, we’ve decided on a more intimate bridal party," or cite family obligations. If someone asks for a reason, explain that as much as you would’ve loved for her to participate, you just couldn’t expand the number.
Confront any problems that arise.
If there’s any trouble in the bridal party, try to smooth things over as soon as possible by having an open, honest discussion. Don’t address anything contentious via e-mail or send a messenger to do your dirty work.
Say thank you.
Expressing your gratitude for your bridesmaids’ time, money and support will make them happy to go on giving it. Acknowledge their efforts, and don’t insist on exotic bachelorette trips or overly extravagant bridesmaids’ ensembles. Treat them to a festive brunch and, finally, give each a thoughtful gift when the wedding comes around.