I asked my three best friends together since we've all been friends since 3rd grade. I asked my two cousins and friend separately. There wasn't any pressure on them since they all knew they would be part of my bridal party some day.
I'm having 2 MOH's and that's it! The plan is to go out for dinner and drinks, and surprise them with little bridesmaid proposal boxes at dinner! One of my MOH's has been my best friend since birth, literally. And the other, we've been best friends for over 10 years and they're both over the moon about it and already know they're going to be a part of my wedding. But I still want to make it special!
I asked one bridesmaid alone, MOH alone, but two other bridesmaids together! The four of them on the whole aren’t individually friends aside from the two I asked together which is why I did it the way I did. I also know the only required cost for them will be their dresses (I plan to keep at or under $50, so far my eye is on a $35 dress, and if it came down to it I would pay for this if they needed it in order to participate) if you think there may be any reason that anyone would feel a need to decline I would ask separately , so that you can have a conversation right away to work through it or allow them to decline without embarrassment
I asked my bridesmaid together as a group during my birthday brunch. It’s hard to get all them together at the same time unless they are celebrating me. I handed them each a card where I hand wrote a poem explaining how I feel about them and that there’s something I’ve been wanting to ask them. I
had bought photo card boxes and printed photos of us from grade school to present and added a bridesmaid wine glass, jewelry and a small bottle of moscato. Then I had scrabble pieces that spelled their name and asking them to be my bridesmaids. Once they accepted, I brought out bridal bags with their names on them. We went to brunch in North Hollywood and told the hostess why I was there and if they could help me surprise my best friends and ask them to be my bridesmaids.