I have been asked to be in 5 weddings, in which I always gladly said yes and was honored too.  In my opinion, you should be specific when you ask (the bridesmaid) so she isn't shocked (if you think her feelings will be hurt or disappointed) I know it is a tough decision and you know your friends “best.”  I was maid of honor in my younger sister's wedding and bridesmaid in all the others.  When I was asked each time I was always asked one on one, in a casual kind of way…”Hey Rachel, I am going to have “x” amount of Bridesmaids in my wedding, I really would love to have you as one. I can't imagine you not being in my wedding would you want to be one of my bridesmaids?”  That is how I was asked almost every time with no mention or confusion about what role I was going to have in each wedding.  *I would ask in an upbeat, really happy, positive way so she can't see the tension that your having.  You will know immediately if she is not happy about being a bridesmaid.  I hope this helps, the last thing a Bride needs is an unhappy member(s).  I was “crazy” enough without all that when I got married.  It will be fine no matter what

Rachel – Virginia Calligrapher