Best Man is Woman
When you pick someone to fill the traditional position of "best man," you should pick the person you are closest to. Although conventionally this role might be filled by a brother, relative, or male friend, do not be afraid to stand up and say "My best man is a woman!" Despite any reservations you may have, the wedding party should be a reflection of you and the relationships that are important to you. They should be people who always have been and will continue to be an important part of your lives.
Having a woman act as the best man will certainly spice up the typical wedding atmosphere. Of course, you will need to make some appropriate changes. First, ensure that your bride-to-be is content with the choice. Remember that you are making these important decisions together. Moreover, if you intend to marry in a religious institution, it might be necessary to confirm your choice with your priest, rabbi, reverend, etc. Ensure that your photographer is aware of her status so that she can be included in the pictures of the groom's party. This practice has become increasingly common, so you should have very little difficulty readying everyone for the change.
If you are worried about introducing your choice as "The Best Woman," you can opt for the phrase, "The Groom's Attendant." This can help to relieve any potential embarrassment she may feel. She should be dressed to accent either the bridesmaids or the groom's men. The decision is between you and your bride, and whichever you choose, each is equally appropriate. If you are going for a humorous approach, you could always dress her in a tuxedo. Your guests will get a kick out of it and it will lighten the formal mood of the ceremony.
When it comes to planning the bachelor party, be sure to discuss the details with her. She may feel uncomfortable about approaching you, or even attending. Let her know your thoughts on the matter. Tell her if you want her to go, what kind of venue you're looking for, and all the particulars. Do not be afraid to discuss strippers and beer kegs with her either. If she is worthy of being your "best man," she is likely to already know your tastes.
The "best man" gives one of the most important toasts at the reception. You may even decide to poke a little fun at her title when you introduce her, easing the tension for any of the traditional guests who do not understand the practice. Make sure that you and your fianc sit down with her and let her know what sort of jokes and poems you find inappropriate. Also, try to provide her with a list of duties she will have to perform as your best man. The more communication you have, the better the outcome.
Do not be afraid to choose a woman to fill the position of "best man." You will be happy to find that many people already accept the practice. If you are concerned about any of your guests' prejudices, it can be a good idea to have your parents or close family members get the word around ahead of time to limit the possibility of surprise. Remember, your wedding day is all about you and your bride to be, and you should have fun with it!