From deciding who gets picked, to choosing dresses, there are many bridesmaid woes to worry about. First thing to do is to select the appropriate time to ask friends to be your bridesmaids. Actually, anytime is good. But, if you really want to set a formal time, it is better to wait until a few of the big wedding details have been decided, such as when and where the wedding is taking place. And, of course, don't wait too long either. They should be given enough time for dress fittings and other arrangements without feeling rushed. Do send each of your bridesmaids-to-be a bouquet with a card or invite the group for a meal. Being a bridesmaid is a big commitment, so you should give her sufficient time to consider it.
A common question on choosing a bridesmaid is whether she has to be unmarried. Well, not really. Usually bridesmaids are unmarried and hence the term maids. If you pick a married friend, she would be called matron of honour instead, and would be wearing something more mature than the typical bridesmaid dress. Most importantly, just try to pick someone who makes you feel confident and happy, someone you can trust to help you out on your big day. Also, if you do not want to start a battle by only asking some, but not all of your friends to be bridesmaids, you can ask them to become unofficial wedding "helpers" or "sisters".
The typical protocol is that the bride pays for the bridesmaids' dresses while the groom bears the cost of the suits for the groomsmen. The transport to and from their homes to the wedding venues have to be well taken care of too. All these may add up to a really big sum of money. However, there are always several options to help you sourcing for cheap dresses and suits.
It is not necessary to have bridesmaids wearing matching dresses. Matching styles may not work as your bridesmaids aren't identical to start with. While styles don't have to match, you can have one common element so the whole look of your bridal party gels. For instance, you can choose the color and fabric that suits all bridesmaids and they pick the style of the dress themselves.