Bridal party proposal individual or as a group

I did mine individually.

I did up "bridesmaid boxes" for each of my girls. I ordered white boxes off Etsy with their names in gold on the top, and when you opened the box on the inside of the lid it said "will you be my bridesmaid?". In each box I had a wine tumbler with the girls name on it, a bracelet with their initial, a bottle of their favourite wine and then a card specific to each girl (ex. one of my bridesmaids is a total plant-mom so she got a card with succulents on it that said "my wedding would succ without you").

2 of my bridesmaids live out of province so I set up with their significant others to facetime me when they got their girlfriends to open it. The rest of my bridesmaids I gave to them individually in person.

I had planned today do it individually, but when I asked the first friend she insisted on helping me get everyone together so we could toast and celebrate. It was actually a really fun bonus day with my girlfriends.

Since my fiance and I only have one standing up for each of us, we had done it individually. If I had more bridemaids standing up for me, I'm sure I would have done it separately. I think it's more personal that way.

I asked my Best Man and each of my groomsmen individually. I did it over lunch with each of them. It feels more personalized and the members are not all from the same social circle so it would be weird for that to be the first meet.