Wedding party proposals!

It's definitely okay to ask at different times, but I wouldn't ask anyone until at least a year until your wedding. A lot can change between now and April 2021

I can share with you firsthand why you shouldn't ask more than 1 year out. I had unofficially asked two of my girlfriends to be my bridesmaid (we were talking wedding and I was like "maybe you'll be a bridesmaid" so they took it as they were which was my fault). Long story short, I decided to have my two cousins as my bridesmaids (my sister and my best friend are my matrons of honor). I had the slightly awkward conversation with them saying "since we are having a small and intimate wedding, I would like to ask my cousins to be my bridesmaids but wanted to run it by you since I technically asked you first." Luckily they were both super understanding about it and said "family comes first; I honesty just want to be part of the bachelorette party haha." So it worked out for me in the end and no one got hurt, but if I could redo it, I wouldn't ask anyone until a year our max.

Typically brides advise asking 8-12 months out. I asked 19 months out and didn't have any problems or drama the entire engagement.