I don't have middle schoolers (yet), but I've been reading Teach your Children Well, and there is a lot of info on middle schoolers in there.

Untangled if you have a girl

I agree with pp above, and I encourage love and logic, love and logic for teens, and helicopters, drill sergeants and consultants.

https://www.loveandlogic.com/collections/parents

PP again - for more general parenting of middle schoolers I have liked Yes Your Teen is Crazy, How to Talk So Kid’s Will Listen and Listen So Kids Will Talk, and The Self Driven Child.

I just read Peggy Orenstein’s Boys and Sex. Read Girls and Sex when it came out. Not a fun read, but necessary, I think!

Can you recommend parenting books that deal with middle school aged kids, especially about issues/attitudes on dating, first love, etc.?